ES2656823T3 - Compuestos fotocrómicos - Google Patents
Compuestos fotocrómicos Download PDFInfo
- Publication number
- ES2656823T3 ES2656823T3 ES11001431.3T ES11001431T ES2656823T3 ES 2656823 T3 ES2656823 T3 ES 2656823T3 ES 11001431 T ES11001431 T ES 11001431T ES 2656823 T3 ES2656823 T3 ES 2656823T3
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- Spain
- Prior art keywords
- phenyl
- naphtho
- pyran
- piperidin
- indene
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 150000001875 compounds Chemical class 0.000 title abstract description 13
- -1 4- (4-fluoro-phenoxycarbonyloxy) -piperidin-1-yl Chemical group 0.000 abstract description 14
- 239000003795 chemical substances by application Substances 0.000 abstract description 7
- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 abstract description 3
- 150000002148 esters Chemical class 0.000 abstract description 3
- MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 abstract description 2
- NEQFBGHQPUXOFH-UHFFFAOYSA-N 4-(4-carboxyphenyl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=C(C(O)=O)C=C1 NEQFBGHQPUXOFH-UHFFFAOYSA-N 0.000 abstract description 2
- 241000282324 Felis Species 0.000 abstract description 2
- GFSXWQUSLTVUBW-UHFFFAOYSA-N 10bh-benzo[h]chromene Chemical compound C1=CC=C2C3OC=CC=C3C=CC2=C1 GFSXWQUSLTVUBW-UHFFFAOYSA-N 0.000 abstract 8
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 abstract 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 4
- YZTJYBJCZXZGCT-UHFFFAOYSA-N phenylpiperazine Chemical compound C1CNCCN1C1=CC=CC=C1 YZTJYBJCZXZGCT-UHFFFAOYSA-N 0.000 abstract 1
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 12
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 6
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- SYUYTOYKQOAVDW-UHFFFAOYSA-N 2-nitrosonaphthalen-1-ol Chemical group C1=CC=C2C(O)=C(N=O)C=CC2=C1 SYUYTOYKQOAVDW-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 125000005605 benzo group Chemical group 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- ZTUKGBOUHWYFGC-UHFFFAOYSA-N 1,3,3-trimethyl-2-methylideneindole Chemical compound C1=CC=C2N(C)C(=C)C(C)(C)C2=C1 ZTUKGBOUHWYFGC-UHFFFAOYSA-N 0.000 description 1
- QEQVCPKISCKMOQ-UHFFFAOYSA-N 3h-benzo[f][1,2]benzoxazine Chemical group C1=CC=CC2=C(C=CNO3)C3=CC=C21 QEQVCPKISCKMOQ-UHFFFAOYSA-N 0.000 description 1
- JSTCPNFNKICNNO-UHFFFAOYSA-N 4-nitrosophenol Chemical compound OC1=CC=C(N=O)C=C1 JSTCPNFNKICNNO-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- MQKPEUAOJLJUMD-UHFFFAOYSA-N phenol;piperazine Chemical compound C1C[NH2+]CCN1.[O-]C1=CC=CC=C1 MQKPEUAOJLJUMD-UHFFFAOYSA-N 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
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- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/78—Ring systems having three or more relevant rings
- C07D311/92—Naphthopyrans; Hydrogenated naphthopyrans
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- C07D311/94—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems condensed with rings other than six-membered or with ring systems containing such rings
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Abstract
Un compuesto fotocrómico: (I) que comprende: (A) al menos un grupo fotocrómico seleccionado entre un pirano, una oxazina y un fúlgido; y (B) al menos un agente de alargamiento unido a al menos un grupo fotocrómico, en donde el al menos un agente de alargamiento se selecciona entre: (1) 4-(4-fluoro-fenoxicarboniloxi)-piperidin-1-ilo; (2) 4-(bifenil-4-carboniloxi)-piperidin-1-ilo; (3) 4-(naftalen-2-carboniloxi)-piperidin-1-ilo; (4) 4-(4-pentadecafluoroheptiloxi-fenilcarbamoil)-benciloxi; (5) 4-(3-piperidin-4-il-propil)-piperidin-1-ilo; (6) éster de bis-[1-nombre del PC]-piperidin-4-ilo] del ácido bifenil-4,4'-dicarboxílico o (II) seleccionado entre: (a) 3-fenil-3-(4-(4-piperidinopiperidino)fenil)-13,13-dimetil-indeno[2',3':3,4]nafto[1,2-b]pirano; (b) 3-fenil-3-(4-(4-fenilpiperazina)fenil)-13,13-dimetil-indeno[2',3':3,4]nafto[1,2-b]pirano; (c) 3-fenil-3-(4-pirrolidin-1-il-fenil)-13,13-dimetil-6-metoxi-7-(4-fenil-piperazin-1-il)indeno[2',3':3,4]nafto[1,2- b]pirano; (d) 3-fenil-3-(4-pirrolidin-1-il-fenil)-13,13-dimetil-6-metoxi-7-([1,4']bipiperidinil-1``-il)indeno[2',3':3,4]nafto[1,2- b]pirano; (e) 3-fenil-3-(4-([1,4']bipiperidinil-1'-il)fenil)-13,13-dimetil-6-metoxi-7-([1,4']bipiperidinil-1'- il)indeno[2',3':3,4]nafto[1,2-b]pirano; (f) 3-fenil-3-(4-([1,4']bipiperidinil-1'-il)fenil)-13,13-dimetil-6-metoxi-7-(4-bencilpiperidin-1-il)indeno[2',3':3,4] nafto[1,2-b]pirano; (g) 3-fenil-3-(4-([1,4']bipiperidinil-1'-il)fenil)-13,13-dimetil-6-metoxi-7-(piperadin-1-il)indeno[2',3':3,4]nafto[1,2- b]pirano; (h) 3-fenil-3-(4-(4-fenil-piperazin-1-il)fenil)-13,13-dimetil-6-metoxi-7-(4-fenil-piperazin-1- il)indeno[2',3':3,4]nafto[1,2-b]pirano; (i) 1,3,3-trimetil-6'-(4-etoxicarbonil)-piperidin-1-il)-espiro[indolina-2,3'-3H-nafto[2,1-b][1,4]oxazina].
Description
(xiv) grupos R1 inmediatamente adyacentes junto a un grupo representado por una de las Fórmulas vii, viii y ix:
5 en donde
(A) W y W’ se seleccionan independientemente en cada ocasión entre -O-, -N(X7)-, -C(X14)-, -C(X17)-, (en donde X7, X14 y X17 son como se han expuesto anteriormente),
(B) X14, X15 y X17 son como se ha expuesto anteriormente y 10 (C) q es un número entero seleccionado entre 0, 1, 2, 3 y 4.
Otra realización no limitante proporciona un compuesto fotocrómico que comprende:
(a) al menos un grupo fotocrómico seleccionado entre un pirano, una oxazina y un fúlgido; y
15 (b) al menos un agente de alargamiento (L) unido al al menos un grupo fotocrómico, en donde el al menos un agente de alargamiento se selecciona entre uno de los siguientes compuestos enumerados (y representados gráficamente) a continuación en la Tabla I.
Tabla I:
- (1) 4-(4-fluoro-fenoxicarboniloxi)-piperidin-1-ilo
- (2) 4-(bifenil-4-carboniloxi)-piperidin-1-ilo
- imagen9
- (3) 4-(naftalen-2-carboniloxi)-piperidin-1-ilo
- (4) 4-(4-pentadecafluoroheptiloxi-fenilcarbamoil)-benciloxi
- (5) 4-(3-piperidin-4-il-propil)-piperidin-1-ilo
- (6) éster bis-[1-nombre del PC]-piperidin-4-ílico] del ácido bifenil4,4’-dicarboxílico
Otra realización no limitante desvelada en el presente documento proporciona un compuesto fotocrómico representado por la Fórmula II:
En referencia a la Fórmula II, A es un anillo aromático o un anillo aromático condensado seleccionado entre: nafto, benzo, fenantro, fluoranteno, anteno, quinolino, tieno, furo, indolo, indolino, indeno, benzofuro, benzotieno, tiofeno, nafto indenocondensado, nafto heterociclocondensado y benzo heterociclocondensado. Además, de acuerdo con diversas realizaciones no limitantes, B y B’ pueden seleccionarse cada uno independientemente entre:
9
(xiii) un anillo que contiene nitrógeno representado por la Fórmula i, que se ha expuesto anteriormente;
(xiv) un grupo representado por una de las Fórmulas ii o iii, que se han expuesto anteriormente; y
(xv) los grupos R3 inmediatamente adyacentes juntos forman un grupo representado por una de las Fórmulas vii, viii o ix, que se han expuesto anteriormente.
5 Además, de acuerdo con diversas realizaciones no limitantes desveladas en el presente documento, el compuesto fotocrómico representado por la Fórmula XII comprende al menos un agente de alargamiento (L) como se ha definido anteriormente.
10 Como se ha analizado anteriormente con respecto a los compuestos fotocrómicos generalmente representados por la Fórmula II desvelados en el presente documento, los compuestos fotocrómicos generalmente representados por la Fórmula XII pueden extenderse en cualquier posición disponible mediante sustitución con L o un grupo R3 sustituido con L, y/o en cualquier dirección deseada mediante distintas combinaciones de sustituciones de posiciones disponibles con L o grupos R3 sustituidos con L. Por lo tanto, por ejemplo, aunque de manera no limitante
15 en el presente documento, los compuestos fotocrómicos generalmente representados por la Fórmula XII pueden extenderse sustituyendo el grupo SP con L o un grupo R3 sustituido con L y/o sustituyendo el grupo A con L o un grupo R3 sustituido con L para proporcionar una relación de absorción promedio deseada para el compuesto fotocrómico.
20 Como se ha analizado anteriormente en referencia a la Fórmula XII, de acuerdo con diversas realizaciones no limitantes desveladas en el presente documento, el grupo SP puede ser indolino. Más específicamente, de acuerdo con diversas realizaciones no limitantes desveladas en el presente documento, el compuestos fotocrómico puede representarse por la Fórmula XIII:
25
en donde cada R’’ se selecciona independientemente en cada ocasión entre hidrógeno, un alquilo sustituido o sin sustituir, cicloalquilo, arilalquilo o juntos forman cicloalquilo que está sustituido o sin sustituir; R’’’ se selecciona entre un grupo alquilo, arilo o arilalquilo que está sin sustituir o sustituido con al menos uno de: (i) -CH(CN)2 o 30 CH(COOX1)2; (ii) -CH(X2)(X3); y (iii) -C(O)X24 (en donde X1, X2, X3 y X24 son como se ha definido anteriormente); y
(iv) halógeno, hidroxi, éster o amina; y en donde al menos uno de i y r es al menos 1 y al menos un R3 comprende L.
Por ejemplo, aunque de manera no limitante en el presente documento, de acuerdo con diversas realizaciones no limitantes desveladas en el presente documento en donde el grupo SP es indolino, el compuesto fotocrómico puede 35 representarse por al menos una de Fórmula XIV y Fórmula XV:
23
Secuencia de reacción I
5 Las secuencias de reacción más específicas para sintetizar los compuestos fotocrómicos de acuerdo con diversas realizaciones no limitantes desveladas en el presente documento y generalmente representadas por la Fórmula XII anterior y más específicamente representadas por la Fórmula XIII anterior, en donde Y es N y SP es indolino se representan a continuación en las Secuencias de reacción J y K.
10 En la Secuencia de reacción J (a continuación), un nitrosofenol representado por la Fórmula φ1 se hace reaccionar en metanol con un agente de alargamiento L, que es piperazino fenol (representado por la Fórmula φ2), para formar el nitrosonaftol sustituido con L representado por la Fórmula φ3. Como se representa en la Secuencia de reacción J, el nitrosonaftol sustituido con L puede además sustituirse con uno o más grupos R, cada uno de los cuales puede comprender un agente de alargamiento L que es igual o diferente a los restantes sustituyentes L. El nitrosonaftol
15 sustituido con L representado por la Fórmula φ3 después se acopla por calentamiento con la base de Fischer representada por la Fórmula φ4 para producir la naftoxazina sustituida con L representada por la Fórmula φ5.
28
Claims (1)
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| JP5377014B2 (ja) * | 2009-03-18 | 2013-12-25 | 株式会社トクヤマ | クロメン化合物の製造方法 |
| CN103282800B (zh) * | 2010-12-27 | 2018-01-23 | Dic株式会社 | 立体图像显示装置用双折射透镜材料和立体图像显示装置用双折射透镜的制造方法 |
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2004
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2006
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