Acetic acid (1S,2R,4R,6R)-1,6-dimethyl-3,9-dioxa-tricyclo[4.2.1.0^2,4]non-4-yl ester | 257860-33-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: Acetic acid (1S,2R,4R,6R)-1,6-dimethyl-3,9-dioxa-tricyclo[4.2.1.0^2,4]non-4-yl ester
• CAS: 257860-33-6
• 化学式: C₁₁H₁₆O₄
• 分子量: 212.246
• InChiKey: WFWLHPXGLITSLB-ZNSHCXBVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.38
• 重原子数：
  15.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  48.06
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (1S,2R,4R,6R)-1,6-dimethyl-3,9-dioxa-tricyclo[4.2.1.0^2,4]non-4-yl ester 在 对甲苯磺酸 、 溶剂黄146 作用下， 以 氯仿 为溶剂， 以94%的产率得到(1S,2S,5R)-2-Hydroxy-1,5-dimethyl-8-oxa-bicyclo[3.2.1]octan-3-one
  参考文献：
  名称：

  Chiral enol acetates derived from prochiral oxabicyclic ketones using enzymes

  摘要：

  Racemic enol acetates 2-4 and 9 derived from prochiral 8-oxabicyclo[3.2.1]oct-6-en-3-ones have been resolved with good enantioselectivity (E=45, 47, 48 and 7.8, respectively) using silica-adsorbed Humicola sp. lipase and the absolute configuration of enol acetate 2 was determined by X-ray crystallographic analysis of the camphanyl derivative 13. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01809-2
• 作为产物：
  描述：

  Acetic acid (1S,5S)-1,5-dimethyl-8-oxa-bicyclo[3.2.1]octa-2,6-dien-3-yl ester 在 palladium on activated charcoal disodium hydrogenphosphate 、 氢气 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 0.17h， 生成 Acetic acid (1S,2R,4R,6R)-1,6-dimethyl-3,9-dioxa-tricyclo[4.2.1.0^2,4]non-4-yl ester
  参考文献：
  名称：

  Chiral enol acetates derived from prochiral oxabicyclic ketones using enzymes

  摘要：

  Racemic enol acetates 2-4 and 9 derived from prochiral 8-oxabicyclo[3.2.1]oct-6-en-3-ones have been resolved with good enantioselectivity (E=45, 47, 48 and 7.8, respectively) using silica-adsorbed Humicola sp. lipase and the absolute configuration of enol acetate 2 was determined by X-ray crystallographic analysis of the camphanyl derivative 13. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01809-2