(9Z)-<11,11,12,12,13,13,14,14,16,16,17,17,18,18,18-(2)H15>octadec-9-en-1-ol | 223487-54-5

• 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: (9Z)-<11,11,12,12,13,13,14,14,16,16,17,17,18,18,18-(2)H15>octadec-9-en-1-ol
• 英文别名: (Z)-11,11,12,12,13,13,14,14,16,16,17,17,18,18,18-pentadecadeuteriooctadec-9-en-1-ol
• CAS: 223487-54-5
• 化学式: C₁₈H₃₆O
• 分子量: 283.364
• InChiKey: ALSTYHKOOCGGFT-KVQWEPJASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  19
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 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：

  (9Z)-<11,11,12,12,13,13,14,14,16,16,17,17,18,18,18-(2)H15>octadec-9-en-1-ol 在 重铬酸吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 以38%的产率得到(9Z)-<11,11,12,12,13,13,14,14,16,16,17,17,18,18,18-(2)H15>octadec-9-enoic acid
  参考文献：
  名称：

  Biosynthesis of epilachnene, a macrocyclic defensive alkaloid of the Mexican bean beetle

  摘要：

  The carbon skeleton of the azamacrolide epilachnene, the principal defensive alkaloid of Epilachna varivestis pupae, can be derived from oleic acid and serine. Analytical evidence from three experiments in which insects were fed [H-2(35)]octadecanoic acid, (Z)-9-[11,11,12,12,13,13,14,14,15,15,16,16,17,17,18,18,18-H-2(17)]octadecenoic acid and (Z)-9-[11,11,12,12,13,13,14,14,16,16,17,17,18,18,18-H-2(15)]octadecenoic acid, indicates that only the C-15 methylene group of oleic acid is involved in the mechanism leading to carbon-nitrogen bond formation in epilachnene. Support for this scheme is provided by the observation of an unusual ion at m/z 170 in the electron-ionization mass spectrum of epilachnene, rationalized as CH2=CH-COO-CH2-CH2-NH+=CH-CH2-CH2-CH3. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)01102-8
• 作为产物：
  描述：

  2-(9-癸炔-1-基氧基)四氢-2H-吡喃 在 P₂-Ni 吡啶 、 氢气 、 对甲苯磺酸 、 sodium iodide 作用下， 以 甲醇 、 乙醇 、 丙酮 为溶剂， 反应 21.5h， 生成 (9Z)-<11,11,12,12,13,13,14,14,16,16,17,17,18,18,18-(2)H15>octadec-9-en-1-ol
  参考文献：
  名称：

  Biosynthesis of epilachnene, a macrocyclic defensive alkaloid of the Mexican bean beetle

  摘要：

  The carbon skeleton of the azamacrolide epilachnene, the principal defensive alkaloid of Epilachna varivestis pupae, can be derived from oleic acid and serine. Analytical evidence from three experiments in which insects were fed [H-2(35)]octadecanoic acid, (Z)-9-[11,11,12,12,13,13,14,14,15,15,16,16,17,17,18,18,18-H-2(17)]octadecenoic acid and (Z)-9-[11,11,12,12,13,13,14,14,16,16,17,17,18,18,18-H-2(15)]octadecenoic acid, indicates that only the C-15 methylene group of oleic acid is involved in the mechanism leading to carbon-nitrogen bond formation in epilachnene. Support for this scheme is provided by the observation of an unusual ion at m/z 170 in the electron-ionization mass spectrum of epilachnene, rationalized as CH2=CH-COO-CH2-CH2-NH+=CH-CH2-CH2-CH3. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)01102-8

文献信息

• Biosynthesis of epilachnene, a macrocyclic defensive alkaloid of the Mexican bean beetle
  作者：Athula B. Attygalle、Aleš Svatoš、Martin Veith、Jay J. Farmer、Jerrold Meinwald、Scott Smedley、Andrés González、Thomas Eisner

  DOI：10.1016/s0040-4020(98)01102-8

  日期：1999.1

  The carbon skeleton of the azamacrolide epilachnene, the principal defensive alkaloid of Epilachna varivestis pupae, can be derived from oleic acid and serine. Analytical evidence from three experiments in which insects were fed [H-2(35)]octadecanoic acid, (Z)-9-[11,11,12,12,13,13,14,14,15,15,16,16,17,17,18,18,18-H-2(17)]octadecenoic acid and (Z)-9-[11,11,12,12,13,13,14,14,16,16,17,17,18,18,18-H-2(15)]octadecenoic acid, indicates that only the C-15 methylene group of oleic acid is involved in the mechanism leading to carbon-nitrogen bond formation in epilachnene. Support for this scheme is provided by the observation of an unusual ion at m/z 170 in the electron-ionization mass spectrum of epilachnene, rationalized as CH2=CH-COO-CH2-CH2-NH+=CH-CH2-CH2-CH3. (C) 1999 Elsevier Science Ltd. All rights reserved.