(E)-2-cyano-4,4,5,5,6,6,6-heptafluoro-1-mesitylhex-1-en-3-one | 459148-20-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-2-cyano-4,4,5,5,6,6,6-heptafluoro-1-mesitylhex-1-en-3-one
• 英文别名: (2E)-4,4,5,5,6,6,6-heptafluoro-3-oxo-2-[(2,4,6-trimethylphenyl)methylidene]hexanenitrile
• CAS: 459148-20-0
• 化学式: C₁₆H₁₂F₇NO
• 分子量: 367.266
• InChiKey: OXFMAXFNNGXRDR-IZZDOVSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  40.9
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (E)-2-cyano-4,4,5,5,6,6,6-heptafluoro-1-mesitylhex-1-en-3-one 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 以79%的产率得到(E)-2-cyano-4,4,5,5,6,6,6-heptafluoro-1-mesityl-1-hexen-3-ol
  参考文献：
  名称：

  Synthetic Organic Chemistry with 2-Ethoxy-2-(phenylselenenyl)perfluoroalk-2-enenitrile:  Application to α-Cyanoperfluoroacylation of Aldehydes

  摘要：

  (Z)- and (E)-2-Ethoxyperfluoro-2-(phenylselenenyl)alk-2-enenitriles 2-4 prepared by our original method underwent transmetalation on treatment with n-BuLi or EtMgBr, and the successive reaction with aldehyde and ketones afforded the corresponding allylic alcohols 10a-f, 9a, and 11a,b in good to high yields. Hydrolysis of the alcohols gave alpha-cyano-alpha,beta-unsaturated perfluoroalkyl ketones 13a-c, 13e, 12a, and 15a. alpha-Cyanoperfluoroalkyl ketones were easily converted to alpha,beta-unsaturated 3-aryl-2-cyanoallylic alcohols 18-22 having interesting biological activities and chemical reactivities.

  DOI：

  10.1021/jo0201880
• 作为产物：
  描述：

  (Z)-2-cyano-3-ethoxy-4,4,5,5,6,6,6-heptafluoro-1-mesitylhex-2-en-1-ol 在 对甲苯磺酸 作用下， 以 1,2-二氯乙烷 为溶剂， 以59%的产率得到(E)-2-cyano-4,4,5,5,6,6,6-heptafluoro-1-mesitylhex-1-en-3-one
  参考文献：
  名称：

  Synthetic Organic Chemistry with 2-Ethoxy-2-(phenylselenenyl)perfluoroalk-2-enenitrile:  Application to α-Cyanoperfluoroacylation of Aldehydes

  摘要：

  (Z)- and (E)-2-Ethoxyperfluoro-2-(phenylselenenyl)alk-2-enenitriles 2-4 prepared by our original method underwent transmetalation on treatment with n-BuLi or EtMgBr, and the successive reaction with aldehyde and ketones afforded the corresponding allylic alcohols 10a-f, 9a, and 11a,b in good to high yields. Hydrolysis of the alcohols gave alpha-cyano-alpha,beta-unsaturated perfluoroalkyl ketones 13a-c, 13e, 12a, and 15a. alpha-Cyanoperfluoroalkyl ketones were easily converted to alpha,beta-unsaturated 3-aryl-2-cyanoallylic alcohols 18-22 having interesting biological activities and chemical reactivities.

  DOI：

  10.1021/jo0201880

文献信息

• Synthetic Organic Chemistry with 2-Ethoxy-2-(phenylselenenyl)perfluoroalk-2-enenitrile:  Application to α-Cyanoperfluoroacylation of Aldehydes
  作者：Mitsuhiro Yoshimatsu、Yoshie Timura

  DOI：10.1021/jo0201880

  日期：2002.8.1

  (Z)- and (E)-2-Ethoxyperfluoro-2-(phenylselenenyl)alk-2-enenitriles 2-4 prepared by our original method underwent transmetalation on treatment with n-BuLi or EtMgBr, and the successive reaction with aldehyde and ketones afforded the corresponding allylic alcohols 10a-f, 9a, and 11a,b in good to high yields. Hydrolysis of the alcohols gave alpha-cyano-alpha,beta-unsaturated perfluoroalkyl ketones 13a-c, 13e, 12a, and 15a. alpha-Cyanoperfluoroalkyl ketones were easily converted to alpha,beta-unsaturated 3-aryl-2-cyanoallylic alcohols 18-22 having interesting biological activities and chemical reactivities.