1-(tetrahydropyran-2-yloxy)-<11,11,12,12,13,13,14,14,15,15,16,16,17,17,18,18,18-(2)H17>octadec-9-yne | 223487-41-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: 1-(tetrahydropyran-2-yloxy)-<11,11,12,12,13,13,14,14,15,15,16,16,17,17,18,18,18-(2)H17>octadec-9-yne
• CAS: 223487-41-0
• 化学式: C₂₃H₄₂O₂
• 分子量: 367.45
• InChiKey: HXLZDWWAMWJMHS-OISRNESJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.01
• 重原子数：
  25.0
• 可旋转键数：
  16.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1-(tetrahydropyran-2-yloxy)-<11,11,12,12,13,13,14,14,15,15,16,16,17,17,18,18,18-(2)H17>octadec-9-yne 在 P₂-Ni 氢气 作用下， 以 乙醇 为溶剂， 反应 1.5h， 生成 (Z)-2-((octadec-9-en-1-yl-11,11,12,12,13,13,14,14,15,15,16,16,17,17,18,18,18-d17)oxy)tetrahydro-2H-pyran
  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：

  1-溴-8-(四氢吡喃氧基)辛烷 在 N,N-二甲基丙烯基脲 、 正丁基锂 作用下， 以 二甲基亚砜 为溶剂， 反应 12.0h， 生成 1-(tetrahydropyran-2-yloxy)-<11,11,12,12,13,13,14,14,15,15,16,16,17,17,18,18,18-(2)H17>octadec-9-yne
  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 Defensive Coccinellidae Alkaloids: Incorporation of Fatty Acids in Adaline, Coccinelline, and Harmonine
  作者：Eveline Haulotte、Pascal Laurent、Jean-Claude Braekman

  DOI：10.1002/ejoc.201101563

  日期：2012.4

  In this study, we report on in vitro incorporation experiments of several labelled fatty acids in the ladybird alkaloids coccinelline (Coccinella 7-punctata), adaline (Adalia 2-punctata), and harmonine (Harmonia axyridis). The obtained results clearly indicate that stearic acid is the precursor of coccinelline and harmonine, whereas myristic acid is at the origin of the carbon skeleton of adaline.

  在这项研究中，我们报告了几种标记脂肪酸在瓢虫生物碱瓢虫碱 (Coccinella 7-punctata)、阿达琳 (Adalia 2-punctata) 和和谐 (Harmonia axyridis) 中的体外掺入实验。所得结果清楚地表明，硬脂酸是瓢虫碱和海葵碱的前体，而肉豆蔻酸是阿达林碳骨架的起源。介绍了这些生物碱生物合成的可能途径。
• 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.