endo-3-(methoxycarbonyl)bicyclo[2.2.1]hept-5-en-exo-2-carboxylic acid

• 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: endo-3-(methoxycarbonyl)bicyclo[2.2.1]hept-5-en-exo-2-carboxylic acid
• 英文别名: endo-3-methoxycarbonylbicyclo[2.2.1]hept-2-ene-2-exo-carboxylic acid；(1R,2R,3R,4S)-3-methoxycarbonylbicyclo[2.2.1]hept-5-ene-2-carboxylic acid
• 化学式: C₁₀H₁₂O₄
• 分子量: 196.203
• InChiKey: JYZKYCYHXBQTCY-LXGUWJNJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  endo-3-(methoxycarbonyl)bicyclo[2.2.1]hept-5-en-exo-2-carboxylic acid 以3%的产率得到
  参考文献：
  名称：

  KLUNDER, A. J. H.;VAN, GASTEL F. J. C.;ZWANENBURG, B., TETRAHEDRON LETT., 29,(1988) N 22, C. 2697-2700

  摘要：

  DOI：
• 作为产物：
  描述：

  tert-butyl methyl fumarate 在 美雄醇 、 三氟乙酸 作用下， 生成 endo-3-(methoxycarbonyl)bicyclo[2.2.1]hept-5-en-exo-2-carboxylic acid
  参考文献：
  名称：

  Enantioselective synthesis of dual serotonergic azanoradamantane SC-52491

  摘要：

  A racemic synthesis of azanoradamantane (+/-)-3 was accomplished via Yamamoto's MAD-catalyzed Diels-Alder protocol. Subsequently, a scalable asymmetric synthesis of azanoradamantane benzamide SC-52491 was carried out employing Helmchen's asymmetric Diels-Alder methodology to construct all four contiguous asymmetric centers with the correct relative stereochemistry and in 99.3% e.e. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00680-8

文献信息

• A Simple Method for Resolution of <i>Endo</i> -/<i>Exo</i> -Monoesters of <i>Trans</i> -Norborn-5-Ene-2,3-Dicarboxylic Acids Into Their Enantiomers
  作者：Vitaly N. Kovalenko、Yurii Yu. Kozyrkov

  DOI：10.1002/chir.22404

  日期：2015.2

  obtainable from trans‐norborn‐5‐ene‐2,3‐dicarboxylic acid methyl and tert‐butyl monoesters was performed by crystallization of the respective salts prepared with (R)‐ and (S)‐1‐phenylethylamine. Starting from racemic endo‐monomethyl ester of trans‐norborn‐5‐ene‐2,3‐dicarboxylic acid, prepared by partial hydrolysis of the cyclopentadiene‐dimethyl fumarate adduct, the corresponding (2R,3R)‐endo‐monoester was

  通过用（R）-和（S）-1-苯基乙胺制备的相应盐进行结晶，可以分离可从反式降冰片烯5烯2,3-二羧酸甲酯和叔丁基单酯获得的旋光异构体。从外消旋起始内切-单甲基酯反-norborn -5-烯-2,3-二羧酸，由环戊二烯富马酸二甲酯加合物的部分水解，相应的（2制备- [R，3 - [R ）-内切-monoester分离在四氯甲烷中反复结晶七次后，其对映体过量（ee）产率为97％。从exo- mono-开始叔丁基相同的酸，由环戊二烯的马来酸酐加合物的醇解制备的酯，随后异构化，（2 - [R，3 - [R ）-外型-monoester物后从乙醇中4个重复结晶分离出> 98％ee的产率。从含有（S）-1-苯乙胺的母液中结晶出酸，生成的产物具有相反的立体化学构型。手性27：151–155，2015。©2014 Wiley Periodicals，Inc.
• New exo/endo selectivity observed in monohydrolysis of dialkyl bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylates
  作者：Satomi Niwayama、Yoshikazu Hiraga

  DOI：10.1016/j.tetlet.2003.09.131

  日期：2003.11

  New monohydrolysis reactions of several exo or endo dimethyl or diethyl bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylates showed higher selectivity toward monohydrolyses of exo-carboalkoxy groups, although the reaction centers are located away from the norbornene rings.

  几个外切或内切二甲基或二乙基双环[2.2.1]庚-5-烯-2,3-二羧酸酯的新的单水解反应显示出对外-羰基烷氧基单水解的更高选择性，尽管反应中心位于远离降冰片烯环的位置。
• Remote Exo/Endo Selectivity in Selective Monohydrolysis of Dialkyl Bicyclo[2.2.1]heptane-2,3-dicarboxylate Derivatives
  作者：Satomi Niwayama、Hanjoung Cho、Masoud Zabet-Moghaddam、Bruce R. Whittlesey

  DOI：10.1021/jo100564e

  日期：2010.6.4

  High exo-facial selectivity was observed in the selective monohydrolysis of a series of near-symmetric diesters that possess an exo-ester group and an endo-ester group attached on a norbornane or norbornene skeleton. The selectivities were found to be clear-cut, although the reaction center in these reactions is one covalent bond distant from the norbornane or norbornene ring, where the difference of the environment between the exo face and endo face is therefore expected to be negligible. The effect of the co-solvent we studied earlier for the selective monohydrolysis reaction was also confirmed and contributed to improvement of the yields of the half-esters.
• Gastel, F. J. C. van; Klunder, A. J. H.; Zwanenburg, B., Recueil des Travaux Chimiques des Pays-Bas, 1991, vol. 110, # 5, p. 175 - 184
  作者：Gastel, F. J. C. van、Klunder, A. J. H.、Zwanenburg, B.

  DOI：——

  日期：——
• KLUNDER, A. J. H.;VAN, GASTEL F. J. C.;ZWANENBURG, B., TETRAHEDRON LETT., 29,(1988) N 22, C. 2697-2700
  作者：KLUNDER, A. J. H.、VAN, GASTEL F. J. C.、ZWANENBURG, B.

  DOI：——

  日期：——