(3aS,6aS)-3a-benzhydryl-6a-methoxy-3,4,5,6-tetrahydro-2H-cyclopenta[b]furan | 461025-76-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (3aS,6aS)-3a-benzhydryl-6a-methoxy-3,4,5,6-tetrahydro-2H-cyclopenta[b]furan
• CAS: 461025-76-3
• 化学式: C₂₁H₂₄O₂
• 分子量: 308.42
• InChiKey: HFJNSKIGWUSJCG-SFTDATJTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3aS,6aS)-3a-benzhydryl-6a-methoxy-3,4,5,6-tetrahydro-2H-cyclopenta[b]furan 生成 8S-8-diphenylmethyl-bicyclo[3.3.0]-1-oxa-6-octene
  参考文献：
  名称：

  Highly efficient chiral resolution and determination of absolute configuration of 2-alkanols by using a cyclopenta[b]furan derivative

  摘要：

  The reaction of 3a-benzhydryi-3,3a,4,5-tetrahydro-2H-cyclopenta[hjfuran and various 2-alkanols in the presence of a catalytic amount of pyridinium 4-tolunesulfonate in dichlorornethane gave 3a-benzhydryl-6a-(1-methyl-aloxy)-hexahydrocyclopenta[b]furan in more than 90% chemical yields. The resulting diastereomeric mixture is easily separable on silica gel chromatography because of the large DeltaR(f) value (briefly 0.1). Absolute configuration of the 2-alkanols can be easily estimated by the chemical shifts of H-1 and C-13 NMR of methyne group of the benzhydryl moiety. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.12.104
• 作为产物：
  描述：

  (+/-)-1-methoxy-5-formylbicyclo[3.3.0]-2-oxaoctane 在 重铬酸吡啶 、 氨 、 4-甲基苯磺酸吡啶 、 lithium 、 乙酰氯 作用下， 以 四氢呋喃 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 69.5h， 生成 (3aS,6aS)-3a-benzhydryl-6a-methoxy-3,4,5,6-tetrahydro-2H-cyclopenta[b]furan
  参考文献：
  名称：

  Highly efficient chiral resolution and determination of absolute configuration of 2-alkanols by using a cyclopenta[b]furan derivative

  摘要：

  The reaction of 3a-benzhydryi-3,3a,4,5-tetrahydro-2H-cyclopenta[hjfuran and various 2-alkanols in the presence of a catalytic amount of pyridinium 4-tolunesulfonate in dichlorornethane gave 3a-benzhydryl-6a-(1-methyl-aloxy)-hexahydrocyclopenta[b]furan in more than 90% chemical yields. The resulting diastereomeric mixture is easily separable on silica gel chromatography because of the large DeltaR(f) value (briefly 0.1). Absolute configuration of the 2-alkanols can be easily estimated by the chemical shifts of H-1 and C-13 NMR of methyne group of the benzhydryl moiety. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.12.104

文献信息

• OPTICAL RESOLVER AND METHOD OF OPTICALLY RESOLVING ALCOHOL WITH THE SAME
  申请人：ZEON CORPORATION

  公开号：EP1364933B1

  公开（公告）日：2007-10-03
• US7674614B2
  申请人：——

  公开号：US7674614B2

  公开（公告）日：2010-03-09
• Highly efficient chiral resolution and determination of absolute configuration of 2-alkanols by using a cyclopenta[b]furan derivative
  作者：Hisao Nemoto、Hiroe Tsutsumi、Satomi Yuzawa、Xian Peng、Weihui Zhong、Jun Xie、Norikazu Miyoshi、Ichiro Suzuki、Masayuki Shibuya

  DOI：10.1016/j.tetlet.2003.12.104

  日期：2004.2

  The reaction of 3a-benzhydryi-3,3a,4,5-tetrahydro-2H-cyclopenta[hjfuran and various 2-alkanols in the presence of a catalytic amount of pyridinium 4-tolunesulfonate in dichlorornethane gave 3a-benzhydryl-6a-(1-methyl-aloxy)-hexahydrocyclopenta[b]furan in more than 90% chemical yields. The resulting diastereomeric mixture is easily separable on silica gel chromatography because of the large DeltaR(f) value (briefly 0.1). Absolute configuration of the 2-alkanols can be easily estimated by the chemical shifts of H-1 and C-13 NMR of methyne group of the benzhydryl moiety. (C) 2003 Elsevier Ltd. All rights reserved.