tricyclo(6.2.1.0^2,7)undeca-4,9-dien-3,6-diol | 28380-02-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: tricyclo(6.2.1.0^2,7)undeca-4,9-dien-3,6-diol
• 英文别名: Tricyclo[6.2.1.02,7]undeca-4,9-diene-3,6-diol
• CAS: 28380-02-1
• 化学式: C₁₁H₁₄O₂
• 分子量: 178.231
• InChiKey: WQYPBLXNPXDCOZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.636
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  乙酸-4-氯苯酯 、 tricyclo(6.2.1.0^2,7)undeca-4,9-dien-3,6-diol 在 novozyme 435 作用下， 以 甲苯 为溶剂， 反应 12.0h， 以81%的产率得到(+)-(1S,4R,4aS,5S,8R,8aS)-5-acetoxy-1,4,4a,5,8,8a-hexahydro-8-hydroxy-endo-1,4-methanonaphthalene
  参考文献：
  名称：

  The influence of microwave irradiation on lipase-catalyzed kinetic resolution of racemic secondary alcohols

  摘要：

  The influence of microwave irradiation on the Novozyme 4350 (Candida antarctica lipase) catalyzed kinetic resolution of secondary alcohols with different functional groups was studied in comparison to the use of conventional heating at 60 degrees C. p-Chlorophenyl acetate was used as an acyl donor and toluene as the solvent. (+/-)-1-Phenyl-1-propanol 1, (+/-)-1-(4-bromophenyl)-propan-1-ol 3, (+/-)-1-phenylbut-3-en-1-ol 5 and (+/-)-3-bromo-2-(2-hydroxypropyl)-1,4-dimethoxynaphthalene 7 were successfully resolved into their (S)-alcohols and (R)-esters, respectively, in good enantiomeric excess. Resolution of (+/-)-ethyl-5-(4-methoxybenyloxy)-3-hydroxypentanoate 9 afforded its (R)-alcohol and (S)-ester using this method. In addition, microwave-assisted lipase transesterification of meso-symmetric diol 11 effected desymmetrization to ester 12 with high enantiomeric excess. In all cases studied, the conversion value for the microwave-assisted lipase kinetic resolution of secondary alcohols was higher than that obtained using conventional heating. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.06.035

文献信息

• The influence of microwave irradiation on lipase-catalyzed kinetic resolution of racemic secondary alcohols
  作者：Prabhakar Bachu、Jennifer S. Gibson、Jonathan Sperry、Margaret A. Brimble

  DOI：10.1016/j.tetasy.2007.06.035

  日期：2007.7

  The influence of microwave irradiation on the Novozyme 4350 (Candida antarctica lipase) catalyzed kinetic resolution of secondary alcohols with different functional groups was studied in comparison to the use of conventional heating at 60 degrees C. p-Chlorophenyl acetate was used as an acyl donor and toluene as the solvent. (+/-)-1-Phenyl-1-propanol 1, (+/-)-1-(4-bromophenyl)-propan-1-ol 3, (+/-)-1-phenylbut-3-en-1-ol 5 and (+/-)-3-bromo-2-(2-hydroxypropyl)-1,4-dimethoxynaphthalene 7 were successfully resolved into their (S)-alcohols and (R)-esters, respectively, in good enantiomeric excess. Resolution of (+/-)-ethyl-5-(4-methoxybenyloxy)-3-hydroxypentanoate 9 afforded its (R)-alcohol and (S)-ester using this method. In addition, microwave-assisted lipase transesterification of meso-symmetric diol 11 effected desymmetrization to ester 12 with high enantiomeric excess. In all cases studied, the conversion value for the microwave-assisted lipase kinetic resolution of secondary alcohols was higher than that obtained using conventional heating. (C) 2007 Elsevier Ltd. All rights reserved.