(8-methoxy-3',3'-dimethyl-6-nitro-3'H-spiro[chromene-2,2'-indol]-1'-yl)-acetic acid ethyl ester | 65792-37-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (8-methoxy-3',3'-dimethyl-6-nitro-3'H-spiro[chromene-2,2'-indol]-1'-yl)-acetic acid ethyl ester
• 英文别名: Ethyl 2-{8-methoxy-3',3'-dimethyl-6-nitro-1',3'-dihydrospiro[chromene-2,2'-indol]-1'-YL}acetate；ethyl 2-(8-methoxy-3',3'-dimethyl-6-nitrospiro[chromene-2,2'-indole]-1'-yl)acetate
• CAS: 65792-37-2
• 化学式: C₂₃H₂₄N₂O₆
• 分子量: 424.453
• InChiKey: HKOGKXZXSOANBD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  93.8
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  3,3-dimethyl-2-methylene-1-ethoxycarbonylmethyl-2,3-dihydro-1H-indole 、 2-羟基-3-甲氧基-5-硝基苯甲醛 以 乙醇 为溶剂， 反应 0.02h， 以43%的产率得到(8-methoxy-3',3'-dimethyl-6-nitro-3'H-spiro[chromene-2,2'-indol]-1'-yl)-acetic acid ethyl ester
  参考文献：
  名称：

  [EN] TIME TEMPERATURE INDICATOR COMPRISING INDOLENIN BASED SPIROPYRANS CONTAINING A N-ACETYLAMIDO OR N- ACETYLESTER SIDE CHAIN
  [FR] INDICATEUR TEMPS-TEMPÉRATURE COMPRENANT DES SPIROPYRANES À BASE D'INDOLÉNINE CONTENANT UNE CHAÎNE LATÉRALE N-ACÉTYLAMIDO OU N-ACÉTYLESTER

  摘要：

  本发明涉及一种时间温度指示器（TTI）系统，其中包括含有N-乙酰氨基或N-乙酰酯侧链的吲哚啉基螺环吡喃，特别是包括至少一种公式（I）的螺环吡喃指示器的时间温度指示器。其中，R1是氢、-C1-C18烷氧基、-C1-C18烷基硫醚、-C1-C18烷基-SO-、-C1-C18烷基-SO2-、苯硫醚、苯、卤素、-C1-C18烷基硫醚、-C1-C18烷基-SO-、-C1-C18烷基-SO2-、苯硫醚、苯、卤素、-C1-C18烷基或-NO2；R2是氢或-C1-C18烷氧基；R3是NO2或卤素；R4是氢、-C1-C18烷氧基或卤素；R5是氢、卤素、-C1-C18烷氧基、-COOH、-COO-C1-C18烷基、-CF3或苯；R6是氢或R6和R7共同形成苯环；R7是氢；Ra是氢或-C1-C6烷基；Rb是氢或-C1-C6烷基，或与Ra共同形成一个5-6成员环；Y是-CH2-COO-R8或-CH2-CO-N（R10）-R9；或CH2-CO-N（R1O）-L-N（R10）CO-CH2-或Y是-CH2-CO-O-L'-O-CO-CH2-其中R8是氢、C3-C18烷基或R8是乙基，条件是R6和R7共同形成苯环；R9是苯、二甲苯、苯-O-苯、苯-S-苯、苯经一次或多次取代的卤素、-CF3、C1-C6烷基、-C1-C6烷氧基、羧基、-COO-C1-C6烷基，其中在多次取代的情况下，取代基可以相同也可以不同；R10是氢、C1-C18烷基；L是1,3-苯撑基或1,4-苯撑基，其中苯撑基可以选择地经一次或多次取代为卤素、-CF3、C1-C18烷氧基、羧基、-COO-C1-C18烷基、-CONH2、-CON（C1-C18烷基）2、硝基；或L是萘、联苯基或苯-O-苯，其中萘、联苯基或苯-O-苯连接基可以选择地经一次或多次取代为卤素、-CF3、C1-C18烷基、-C1-C18烷氧基、羧基、-COO-C1-C18烷基、-CONH2、-CON（C1-C18烷基）2、硝基；L'是1,3-苯撑基或1,4-苯撑基，其中苯撑基可以选择地经一次或多次取代为卤素、CF3、C1-C18烷基、-C1-C18烷氧基、羧基、-COO-C1-C18烷基、-CON（C1-C18烷基）2、硝基；或L是萘、联苯-O-苯，其中萘、联苯基或苯-O-苯连接基可以选择地经一次或多次取代为卤素、-CF3、C1-C18烷基、-C1-C18烷氧基、羧基、-COO-C1-C18烷基、-CONH2、-CON（C1-C18烷基）2、硝基。

  公开号：

  WO2009141237A1

文献信息

• [EN] TIME TEMPERATURE INDICATOR COMPRISING INDOLENIN BASED SPIROPYRANS CONTAINING A N-ACETYLAMIDO OR N- ACETYLESTER SIDE CHAIN<br/>[FR] INDICATEUR TEMPS-TEMPÉRATURE COMPRENANT DES SPIROPYRANES À BASE D'INDOLÉNINE CONTENANT UNE CHAÎNE LATÉRALE N-ACÉTYLAMIDO OU N-ACÉTYLESTER
  申请人：BASF SE

  公开号：WO2009141237A1

  公开（公告）日：2009-11-26

  The present invention relates to time-temperature indicator (TTI) systems comprising indolenin based spiropyrans containing a N-acetylamido or N-acetylester side chain, especially to a time temperature indicator comprising at least one spiropyran indicator of formula (I) Wherein R1 is hydrogen, -C1-C18 alkoxy, -C1-C18 alkylthio, -C1-C18 alkyl-SO-, -C1C18 alkyl-SO2-, phenylthio, phenyl, halogen, -C1-C18 alkylthio, -C1-C18 alkyl-SO-, -C1-C18 alkyl-SO2-, phenylthio, phenyl, halogen, -C1-C18 alkyl or -NO2; R2 is hydrogen or -C1-C18 alkoxy; R3 is NO2 or halogen; R4 is hydrogen, -C1-C18 alkoxy or halogen; R5 is hydrogen, halogen, -C1-C18 alkoxy, -COOH, -COO-C1-C18alkyl, -CF3 or phenyl; R6 is hydrogen or R6 and R7 form together a phenyl ring; R7 is hydrogen; Ra is hydrogen or -C1-C6 alkyl; Rb is hydrogen or -C1-C6 alkyl, or together with Ra form a 5-6 membered ring; Y is -CH2-COO-R8 or -CH2-CO-N(R10)-R9; or CH2-CO-N(R1O)-L-N(R10) CO-CH2- or Y is -CH2-CO-O-L'-O-CO-CH2- wherein R8 is hydrogen, C3-C18alkyl or R8 is ethyl with the proviso that R6 and R7 form together a phenyl ring; R9 is phenyl, mesityl, phenyl-O-phenyl, phenyl-S-phenyl, phenyl once or more than once substituted by halogen, -CF3, C1-C6alkyl, -C1-C6 alkoxy, carboxy, -COO-C1-C6alkyl whereby in case of a more than once substitution, the substituent can be the same or different; R10 is hydrogen, C1-C18alkyl; L is 1,3 phenylene or 1,4 phenylene wherein the phenylene linker is optionally substituted by once or more than once by halogen, -CF3, C1-C18 alkoxy, carboxy, -COO-C1-C18alkyl, -CONH2, -CON(C1-C18alkyl)2, nitro; or L is naphthalene, biphenylene or phenylene-O-phenylene wherein the naphthalene, biphenylene or phenylene-O-phenylene linker is optionally substituted once or more than once by halogen, -CF3, C1-C18alkyl, -C1-C18 alkoxy, carboxy, -COO-C1-C18alkyl, -CONH2, -CON(C1-C18alkyl)2, nitro; L' is 1,3 phenylene or 1,4 phenylene wherein the phenylene linker is optionally substituted by once or more than once by halogen, CF3, C1-C18alkyl, -C1-C18 alkoxy, carboxy, -COO-C1-C18alkyl, -CON(C1-C18alkyl)2, nitro; or L is naphthalene, biphenylene-O-phenylene wherein the naphtalene, biphenylene or phenylene-O-phenylene linker is optionally substituted once or more than once by halogen, -CF3, C1-C18alkyl, - C1-C18 alkoxy, carboxy, -COO-C1-C18alkyl, -CONH2, - CON(C1-C18alkyl)2, nitro.

  本发明涉及一种时间温度指示器（TTI）系统，其中包括含有N-乙酰氨基或N-乙酰酯侧链的吲哚啉基螺环吡喃，特别是包括至少一种公式（I）的螺环吡喃指示器的时间温度指示器。其中，R1是氢、-C1-C18烷氧基、-C1-C18烷基硫醚、-C1-C18烷基-SO-、-C1-C18烷基-SO2-、苯硫醚、苯、卤素、-C1-C18烷基硫醚、-C1-C18烷基-SO-、-C1-C18烷基-SO2-、苯硫醚、苯、卤素、-C1-C18烷基或-NO2；R2是氢或-C1-C18烷氧基；R3是NO2或卤素；R4是氢、-C1-C18烷氧基或卤素；R5是氢、卤素、-C1-C18烷氧基、-COOH、-COO-C1-C18烷基、-CF3或苯；R6是氢或R6和R7共同形成苯环；R7是氢；Ra是氢或-C1-C6烷基；Rb是氢或-C1-C6烷基，或与Ra共同形成一个5-6成员环；Y是-CH2-COO-R8或-CH2-CO-N（R10）-R9；或CH2-CO-N（R1O）-L-N（R10）CO-CH2-或Y是-CH2-CO-O-L'-O-CO-CH2-其中R8是氢、C3-C18烷基或R8是乙基，条件是R6和R7共同形成苯环；R9是苯、二甲苯、苯-O-苯、苯-S-苯、苯经一次或多次取代的卤素、-CF3、C1-C6烷基、-C1-C6烷氧基、羧基、-COO-C1-C6烷基，其中在多次取代的情况下，取代基可以相同也可以不同；R10是氢、C1-C18烷基；L是1,3-苯撑基或1,4-苯撑基，其中苯撑基可以选择地经一次或多次取代为卤素、-CF3、C1-C18烷氧基、羧基、-COO-C1-C18烷基、-CONH2、-CON（C1-C18烷基）2、硝基；或L是萘、联苯基或苯-O-苯，其中萘、联苯基或苯-O-苯连接基可以选择地经一次或多次取代为卤素、-CF3、C1-C18烷基、-C1-C18烷氧基、羧基、-COO-C1-C18烷基、-CONH2、-CON（C1-C18烷基）2、硝基；L'是1,3-苯撑基或1,4-苯撑基，其中苯撑基可以选择地经一次或多次取代为卤素、CF3、C1-C18烷基、-C1-C18烷氧基、羧基、-COO-C1-C18烷基、-CON（C1-C18烷基）2、硝基；或L是萘、联苯-O-苯，其中萘、联苯基或苯-O-苯连接基可以选择地经一次或多次取代为卤素、-CF3、C1-C18烷基、-C1-C18烷氧基、羧基、-COO-C1-C18烷基、-CONH2、-CON（C1-C18烷基）2、硝基。
• TIME TEMPERATURE INDICATOR COMPRISING INDOLENIN BASED SPIROPYRANS CONTAINING A N-ACETYLAMIDO OR N- ACETYLESTER SIDE CHAIN
  申请人：BASF SE

  公开号：EP2291382B1

  公开（公告）日：2011-12-14
• TIME TEMPERATURE INDICATOR COMPRISING INDOLENIN BASED SPIROPYRANS CONTAINING A N-ACETYLAMIDO OR N-ACETYLESTER SIDE CHAIN
  申请人：Feiler Leonhard

  公开号：US20110139059A1

  公开（公告）日：2011-06-16

  The present invention relates to time-temperature indicator (TTI) systems comprising indolenin based spiropyrans containing a N-acetylamido or N-acetylester side chain, especially to a time temperature indicator comprising at least one spiropyran indicator of formula (I) Wherein R 1 is hydrogen, —C 1 -C 18 alkoxy, —C 1 -C 18 alkylthio, —C 1 -C 18 alkyl-SO—, —C 1 -C 18 alkyl-SO 2 —, phenylthio, phenyl, halogen, —C 1 -C 18 alkylthio, —C 1 -C 18 alkyl-SO—, —C 1 -C 18 alkyl-SO 2 —, phenylthio, phenyl, halogen, —C 1 -C 18 alkyl or —NO 2 ; R 2 is hydrogen or —C 1 -C 18 alkoxy; R 3 is NO 2 or halogen; R 4 is hydrogen, —C 1 -C 18 alkoxy or halogen; R 5 is hydrogen, halogen, —C 1 -C 18 alkoxy, —COOH, —COO—C 1 -C 18 alkyl, —CF 3 or phenyl; R 6 is hydrogen or R 6 and R 7 form together a phenyl ring; R 7 is hydrogen; R a is hydrogen or —C 1 -C 6 alkyl; R b is hydrogen or —C 1 -C 6 alkyl, or together with R a form a 5-6 membered ring; Y is —CH 2 —COO—R 8 or —CH 2 —CO—N(R 10 )—R 9 ; or CH 2 —CO—N(R 10 )-L-N(R 10 ) CO—CH 2 — or Y is —CH 2 —CO—O-L′-O—CO—CH 2 — wherein R 8 is hydrogen, C 3 -C 18 alkyl or R 8 is ethyl with the proviso that R 6 and R 7 form together a phenyl ring; R 9 is phenyl, mesityl, phenyl-O-phenyl, phenyl-S-phenyl, phenyl once or more than once substituted by halogen, —CF 3 , C 1 -C 6 alkyl, —C 1 -C 6 alkoxy, carboxy, —COO—C 1 -C 6 alkyl whereby in case of a more than once substitution, the substituent can be the same or different; R 10 is hydrogen, C 1 -C 18 alkyl; L is 1,3 phenylene or 1,4 phenylene wherein the phenylene linker is optionally substituted by once or more than once by halogen, —CF 3 , C 1 -C 18 alkoxy, carboxy, —COO—C 1 -C 18 alkyl, —CONH2, —CON(C 1 -C 18 alkyl) 2 , nitro; or L is naphthalene, biphenylene or phenylene-O-phenylene wherein the naphthalene, biphenylene or phenylene-O-phenylene linker is optionally substituted once or more than once by halogen, —CF 3 , C 1 -C 18 alkyl, —C 1 -C 18 alkoxy, carboxy, —COO—C 1 -C 18 alkyl, —CONH 2 , —CON(C 1 -C 18 alkyl) 2 , nitro; L′ is 1,3 phenylene
• Photochromic properties of some N-substituted 3,3-dimethyl-6?-nitroindoline-2-spiro-2?-2H-chromenes
  作者：M. A. Gal'bershtam、N. M. Przhiyalgovskaya、O. R. Khrolova、I. B. Lazarenko、G. K. Bobyleva、N. N. Suvorov

  DOI：10.1007/bf00469891

  日期：1977.12