methyl 10-(2-hexylcyclopropyl)decanoate | 5965-63-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl 10-(2-hexylcyclopropyl)decanoate
• 英文别名: Methyl-11,12-methylenoctadecanoat；11,12-Methylenoctadecanomethylat；11,12-Methylen-octadecansaeure-methylester；11,12-methyleneoctadecanoate methyl ester
• CAS: 5965-63-9
• 化学式: C₂₀H₃₈O₂
• 分子量: 310.521
• InChiKey: HASAQWANQLNRRS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  22
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.95
• 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：

  2-苄氧基-1,3-丙二醇 、 methyl 10-(2-hexylcyclopropyl)decanoate 在 Lipase PS 作用下， 以 氯仿 为溶剂， 反应 144.0h， 以0.7%的产率得到10-(2-Hexyl-cyclopropyl)-decanoic acid 2-benzyloxy-3-[10-(2-hexyl-cyclopropyl)-decanoyloxy]-propyl ester
  参考文献：
  名称：

  Synthesis of a Novel Lysophosphatidylcholine

  摘要：

  The novel lysophosphatidylcholine (1), which naturally occurs in the marine sponge Spirastrella abata and was reported to inhibit cholesterol biosynthesis in the Chang liver cell, has been synthesized in four steps from methyl cis-11-octadecenoate (2).

  DOI：

  10.1021/np000222a
• 作为产物：
  描述：

  顺式-11-十八烯酸甲酯 以82.1%的产率得到methyl 10-(2-hexylcyclopropyl)decanoate
  参考文献：
  名称：

  An unexpected reversal of fluorine substituent effects in the biomethylenation of two positional isomers: a serendipitous discovery

  摘要：

  The mechanism of biological cyclopropyl fatty acid biosynthesis as it occurs in Lactobacillus plantarum has been probed using fluorine substituent effects. It has been shown that the pattern of rate retardations induced by homoallylic fluorine substitution is numerically the same but opposite in sense for two series of olefinic fatty acid substrates bearing the double bond at either the 9- or the 11-position.

  DOI：

  10.1021/jo00313a004

文献信息

• Synthesis of a Novel Lysophosphatidylcholine
  作者：Changjin Zhu、Tatsuya Morimoto、Shuhei Nakajima、Teruhiko Nitoda、Naomichi Baba

  DOI：10.1021/np000222a

  日期：2001.1.1

  The novel lysophosphatidylcholine (1), which naturally occurs in the marine sponge Spirastrella abata and was reported to inhibit cholesterol biosynthesis in the Chang liver cell, has been synthesized in four steps from methyl cis-11-octadecenoate (2).
• An unexpected reversal of fluorine substituent effects in the biomethylenation of two positional isomers: a serendipitous discovery
  作者：Peter H. Buist、Robert A. Pon

  DOI：10.1021/jo00313a004

  日期：1990.12

  The mechanism of biological cyclopropyl fatty acid biosynthesis as it occurs in Lactobacillus plantarum has been probed using fluorine substituent effects. It has been shown that the pattern of rate retardations induced by homoallylic fluorine substitution is numerically the same but opposite in sense for two series of olefinic fatty acid substrates bearing the double bond at either the 9- or the 11-position.