Acetic acid (1R,2R,3R,4S)-3-hydroxymethyl-bicyclo[2.2.1]hept-5-en-2-ylmethyl ester | 123231-73-2

• 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: Acetic acid (1R,2R,3R,4S)-3-hydroxymethyl-bicyclo[2.2.1]hept-5-en-2-ylmethyl ester
• 英文别名: [(1R,2R,3R,4S)-3-(hydroxymethyl)-2-bicyclo[2.2.1]hept-5-enyl]methyl acetate
• CAS: 123231-73-2
• 化学式: C₁₁H₁₆O₃
• 分子量: 196.246
• InChiKey: GRQPTGXDINMECF-LMLFDSFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Acetic acid (1R,2R,3R,4S)-3-hydroxymethyl-bicyclo[2.2.1]hept-5-en-2-ylmethyl ester 生成
  参考文献：
  名称：

  Enzymatic resolution of norbor(NE)nylmethanols in organic media and an application to the synthesis of (+)- and (−)-endo-Norbornene lactone.

  摘要：

  The enzymatic resolution of some norbornene carboxylic acids, norbornenylmethanols and -methylamines was evaluated. The kinetic resolution of norbornyl- and norbornenylmethanols by Porcine Pancreatic Lipase (PPL)-catalyzed transesterification in methyl acetate as the solvent leads to corresponding acetates and remaining methanols both of high enantiomeric purity. A useful application is the synthesis of both enantiomers of endo-norbornene lactone 8n via transesterification of iodolactone 18. The influence of structural variations on the efficiency of the PPL-catalyzed resolution of lactone methanols 21, 23, 25 and 28, at the optimal reaction conditions established for iodolactone 18, was investigated.

  DOI：

  10.1016/s0040-4020(01)80984-4
• 作为产物：
  描述：

  降冰片烯-2,3-二羧酸 在 lithium aluminium tetrahydride 作用下， 反应 44.0h， 生成 Acetic acid (1R,2R,3R,4S)-3-hydroxymethyl-bicyclo[2.2.1]hept-5-en-2-ylmethyl ester
  参考文献：
  名称：

  Enzymatic resolution of norbor(NE)nylmethanols in organic media and an application to the synthesis of (+)- and (−)-endo-Norbornene lactone.

  摘要：

  The enzymatic resolution of some norbornene carboxylic acids, norbornenylmethanols and -methylamines was evaluated. The kinetic resolution of norbornyl- and norbornenylmethanols by Porcine Pancreatic Lipase (PPL)-catalyzed transesterification in methyl acetate as the solvent leads to corresponding acetates and remaining methanols both of high enantiomeric purity. A useful application is the synthesis of both enantiomers of endo-norbornene lactone 8n via transesterification of iodolactone 18. The influence of structural variations on the efficiency of the PPL-catalyzed resolution of lactone methanols 21, 23, 25 and 28, at the optimal reaction conditions established for iodolactone 18, was investigated.

  DOI：

  10.1016/s0040-4020(01)80984-4

文献信息

• Enzyme mediated optical resolution of endo-norbornene lactone
  作者：A.J.M. Janssen、A.J.H. Klunder、B. Zwanenburg

  DOI：10.1016/s0040-4039(00)97284-8

  日期：1990.1

  The enzymatic resolution of some norbornene esters, -carboxylic acids and -methanols was evaluated. Good results were obtained for the Porcine Pancreatic Lipase (PPL) catalyzed transesterification of norbornene methanols 12 and 13 in methyl acetate. A formal kinetic resolution of endo-norbornene lactone 7 could be achieved through the PPL-catalyzed transesterification of iodolactone 15 in methyl acetate

  评估了一些降冰片烯酯，-羧酸和-甲醇的酶促拆分。猪胰脂肪酶（PPL）催化降冰片烯甲醇12和13在乙酸甲酯中的酯交换反应获得了良好的结果。内降冰片烯内酯7的正式动力学拆分可以通过PPL催化碘代内酯15在乙酸甲酯中的酯交换反应来实现。内酯7的两种对映异构体均以良好的总收率获得对映体纯。
• Enzymatic preparation of optically active bicyclo[2.2.1]heptene derivatives, building blocks for terpenoid natural products. An attractive alternative to enantioselective Diels–Alder syntheses
  作者：J. Van der Eycken、M. Vandewalle、G. Heinemann、K. Laumen、M. P. Schneider、J. Kredel、J. Sauer

  DOI：10.1039/c39890000306

  日期：——

  Bicyclo[2.2.1]heptene derivatives (1)–(3), building blocks for terpenoid natural products, have been prepared with high enantiometric purities by enzymatic hydrolysis of their racemic esters in the presence of porcine liver esterase (PLE) and an ester hydrolase from Pseudomonas sp. (SAM-II).

  双环[2.2.1]庚烯衍生物（1）-（3）是萜类天然产物的组成部分，已通过在猪肝酯酶（PLE）和一种酯的存在下对其外消旋酯进行酶水解，以高对映体纯度制备假单胞菌（Pseudomonas sp）的水解酶。（SAM-II）。
• VAN, DER EYCKEN J.;VANDEWALLE, M.;HEINEMANN, G.;LAUMEN, K.;SCHNEIDER, M. +, J. CHEM. SOC. CHEM. COMMUN.,(1989) N, C. 306-308
  作者：VAN, DER EYCKEN J.、VANDEWALLE, M.、HEINEMANN, G.、LAUMEN, K.、SCHNEIDER, M. +

  DOI：——

  日期：——