(4S,5R)-p-mentha-1,8-diene-5-acetate | 890711-67-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (4S,5R)-p-mentha-1,8-diene-5-acetate
• 英文别名: Acetic acid 3-methyl-6beta-isopropenyl-3-cyclohexene-1alpha-yl ester；[(1R,6S)-3-methyl-6-prop-1-en-2-ylcyclohex-3-en-1-yl] acetate
• CAS: 890711-67-8
• 化学式: C₁₂H₁₈O₂
• 分子量: 194.274
• InChiKey: JKPZFVIXMYNENT-NWDGAFQWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (4S,5R)-p-mentha-1,8-diene-5-acetate 在 草酰氯 、 L-Selectride 、 potassium carbonate 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 (1S,6S)-3-methyl-6-(prop-1-en-2-yl)cyclohex-3-enol
  参考文献：
  名称：

  Enzyme-mediated preparation of enantioenriched forms of trans- and cis-p-menthan-1,8-dien-5-ol

  摘要：

  The synthesis of the trans-p-menthan-5-ol (+/-)-1 was carried out by Diels-Alder cycloaddition of 3-keto-1-butenyl-acetate 3 with isoprene followed by Wittig methylenation. PS lipase resolution of the alcohol afforded acetate (-)-5 with 98% ec, which was hydrolysed to give (-)1. Alternatively, enzymatic hydrolysis of a keto ester followed by Wittig methylenation and hydrolysis afforded the same alcohol with an ee of 86%. The cis-p-menthan-5-ol (-)-2 was obtained by Swern oxidation of (-)-1. followed by diastereoselective reduction with L-Selectride without lost of enantiomeric excess. (c) 2006 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetasy.2006.02.012
• 作为产物：
  描述：

  3-oxo-1-butenyl acetate 在 正丁基锂 、 phosphate buffer 、 Burkholderia cepacia PS lipase 、 三氟化硼乙醚 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 75.5h， 生成 (4S,5R)-p-mentha-1,8-diene-5-acetate
  参考文献：
  名称：

  Enzyme-mediated preparation of enantioenriched forms of trans- and cis-p-menthan-1,8-dien-5-ol

  摘要：

  The synthesis of the trans-p-menthan-5-ol (+/-)-1 was carried out by Diels-Alder cycloaddition of 3-keto-1-butenyl-acetate 3 with isoprene followed by Wittig methylenation. PS lipase resolution of the alcohol afforded acetate (-)-5 with 98% ec, which was hydrolysed to give (-)1. Alternatively, enzymatic hydrolysis of a keto ester followed by Wittig methylenation and hydrolysis afforded the same alcohol with an ee of 86%. The cis-p-menthan-5-ol (-)-2 was obtained by Swern oxidation of (-)-1. followed by diastereoselective reduction with L-Selectride without lost of enantiomeric excess. (c) 2006 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetasy.2006.02.012

文献信息

• Enzyme-mediated preparation of enantioenriched forms of trans- and cis-p-menthan-1,8-dien-5-ol
  作者：Elisabetta Brenna、Claudio Fuganti、Francesco G. Gatti、Marco Perego、Stefano Serra

  DOI：10.1016/j.tetasy.2006.02.012

  日期：2006.3

  The synthesis of the trans-p-menthan-5-ol (+/-)-1 was carried out by Diels-Alder cycloaddition of 3-keto-1-butenyl-acetate 3 with isoprene followed by Wittig methylenation. PS lipase resolution of the alcohol afforded acetate (-)-5 with 98% ec, which was hydrolysed to give (-)1. Alternatively, enzymatic hydrolysis of a keto ester followed by Wittig methylenation and hydrolysis afforded the same alcohol with an ee of 86%. The cis-p-menthan-5-ol (-)-2 was obtained by Swern oxidation of (-)-1. followed by diastereoselective reduction with L-Selectride without lost of enantiomeric excess. (c) 2006 Published by Elsevier Ltd.