(+/-)-6,6-dimethylhept-2-en-4-ol | 176550-31-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (+/-)-6,6-dimethylhept-2-en-4-ol
• 英文别名: (E)-6,6-dimethylhept-2-en-4-ol
• CAS: 176550-31-5
• 化学式: C₉H₁₈O
• 分子量: 142.241
• InChiKey: GWBRMLZVVFLSQN-AATRIKPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (+/-)-6,6-dimethylhept-2-en-4-ol 、 丁酰氯 在 吡啶 作用下， 以 乙醚 为溶剂， 反应 24.0h， 以83%的产率得到1-(2,2-dimethylpropyl)but-2-enyl butanoate
  参考文献：
  名称：

  Kinetic resolution of racemic secondary aliphatic allylic alcohols in lipase-catalyzed transesterification

  摘要：

  Different lipases were screened as biocatalysts in the kinetic resolution process of (+/-)-hept-1-en-3-ol 1, (+/-)-5-methylhex-1-en3-ol 2, (+/-)-6-methythept-2-en-4-ol 3, (+/-)-6,6-dimethylhept-2-en-4-ol 4, and 1-phenylbut-3-en-2-ol 5 by enantio selective transesterification. The acylation of (+/-)-l and (+/-)-2 catalyzed by Novozym 435 (Candida antarctica) was very effective and proceeded with good enantioselectivity. After 4-8 h of reactions the esters formed and the alcohols, which remained were obtained with high enantiomeric excess with 97-100% ee and 91-100% ee, respectively. The lipase Amano PS (Burkholderia cepacia) was the best catalyst in the asymmetric transesterification of (+/-)-5 affording the (R)-alcohol with 90-95% ee and the (S)-ester with 98-100% ce. Low enantio selectivities were observed in the cases of lipase-catalyzed acylation of (+/-)-3 and (+/-)-4. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.12.020
• 作为产物：
  描述：

  巴豆醛 、 1-溴-2,2-二甲基丙烷 在 magnesium 作用下， 以 乙醚 为溶剂， 以68%的产率得到(+/-)-6,6-dimethylhept-2-en-4-ol
  参考文献：
  名称：

  Kinetic resolution of racemic secondary aliphatic allylic alcohols in lipase-catalyzed transesterification

  摘要：

  Different lipases were screened as biocatalysts in the kinetic resolution process of (+/-)-hept-1-en-3-ol 1, (+/-)-5-methylhex-1-en3-ol 2, (+/-)-6-methythept-2-en-4-ol 3, (+/-)-6,6-dimethylhept-2-en-4-ol 4, and 1-phenylbut-3-en-2-ol 5 by enantio selective transesterification. The acylation of (+/-)-l and (+/-)-2 catalyzed by Novozym 435 (Candida antarctica) was very effective and proceeded with good enantioselectivity. After 4-8 h of reactions the esters formed and the alcohols, which remained were obtained with high enantiomeric excess with 97-100% ee and 91-100% ee, respectively. The lipase Amano PS (Burkholderia cepacia) was the best catalyst in the asymmetric transesterification of (+/-)-5 affording the (R)-alcohol with 90-95% ee and the (S)-ester with 98-100% ce. Low enantio selectivities were observed in the cases of lipase-catalyzed acylation of (+/-)-3 and (+/-)-4. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.12.020