1-chloro-4-(2,6,6-trimethylcyclohexenyl)-3-butenoate | 88981-43-5

• 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: 1-chloro-4-(2,6,6-trimethylcyclohexenyl)-3-butenoate
• 英文别名: β-Ionone α'-Chloromethyl Ketone；(E)-1-chloro-4-(2,6,6-trimethylcyclohexen-1-yl)but-3-en-2-one
• CAS: 88981-43-5
• 化学式: C₁₃H₁₉ClO
• 分子量: 226.746
• InChiKey: DNFOYTDKFKOKES-VOTSOKGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  氰甲基磷酸二乙酯 、 1-chloro-4-(2,6,6-trimethylcyclohexenyl)-3-butenoate 在 正丁基锂 作用下， 生成 trans-3-(chloromethyl)-5-(2,6,6-trimethylcyclohexenyl)-2,4-pentadienenitrile 、 trans-3-(chloromethyl)-5-(2,6,6-trimethylcyclohexenyl)-2,4-pentadienenitrile
  参考文献：
  名称：

  Synthesis of 19-Fluororetinal and 20-Fluororetinal

  摘要：

  We have investigated methods to monofluorinate the methyl positions 19 and 20 in retinal, and we describe a general, mild strategy that proceeds in high yields and is compatible with current carbon-13 labeling strategies. The new sequence consists of the conversion of N-methoxy-N-methylamides via the alpha-chloromethyl ketone to the corresponding gamma-hydroxy nitrile, which can subsequently be fluorinated by (diethylamido)sulfur trifluoride (DAST).

  DOI：

  10.1021/jo970162m
• 作为产物：
  描述：

  beta-紫罗酮 在 N-氯代丁二酰亚胺 、 lithium diisopropyl amide 作用下， 生成 1-chloro-4-(2,6,6-trimethylcyclohexenyl)-3-butenoate
  参考文献：
  名称：

  A convenient and simple method for the .alpha.'-chlorination of .alpha.,.beta. and conjugated ketones

  摘要：

  DOI：

  10.1021/jo00181a033

文献信息

• Synthesis of 19-Fluororetinal and 20-Fluororetinal
  作者：Michel Groesbeek、Steven O. Smith

  DOI：10.1021/jo970162m

  日期：1997.5.1

  We have investigated methods to monofluorinate the methyl positions 19 and 20 in retinal, and we describe a general, mild strategy that proceeds in high yields and is compatible with current carbon-13 labeling strategies. The new sequence consists of the conversion of N-methoxy-N-methylamides via the alpha-chloromethyl ketone to the corresponding gamma-hydroxy nitrile, which can subsequently be fluorinated by (diethylamido)sulfur trifluoride (DAST).
• A convenient and simple method for the .alpha.'-chlorination of .alpha.,.beta. and conjugated ketones
  作者：Alfin D. N. Vaz、Guenther Schoellmann

  DOI：10.1021/jo00181a033

  日期：1984.4