Methyl 16-hydroxyhexadeca-5,8,11,14-tetraynoate | 741675-26-3

• 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 16-hydroxyhexadeca-5,8,11,14-tetraynoate
• CAS: 741675-26-3
• 化学式: C₁₇H₁₈O₃
• 分子量: 270.328
• InChiKey: WIYDVMGDWWWOGF-UHFFFAOYSA-N

物化性质

• 沸点：
  441.5±45.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Methyl 16-hydroxyhexadeca-5,8,11,14-tetraynoate 在 lithium hydroxide 、 copper(l) iodide 、 四溴化碳 、 nickel boride (P-2 Ni) 、 氢气 、 potassium carbonate 、 三苯基膦 、 sodium iodide 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 22.5h， 生成 (5Z,8Z,11Z,14Z)-21-Chloro-henicosa-5,8,11,14-tetraen-17-ynoic acid
  参考文献：
  名称：

  A synthetic route to anandamide analogues carrying a substituent at the terminal carbon and an acetylene group in the end pentyl chain

  摘要：

  A versatile sequence is developed for the synthesis of' anandamide analogues with an acetylene group in the end pentyl chain carrying a substituent at the terminal carbon of the chain. These analogues are important for SAR studies of the endocannabinoid. anandamide. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.05.071
• 作为产物：
  描述：

  13-hydroxytrideca-5,8,11-triynoic acid methyl ester 在 copper(l) iodide 、 四溴化碳 、 potassium carbonate 、 三苯基膦 、 sodium iodide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 49.5h， 生成 Methyl 16-hydroxyhexadeca-5,8,11,14-tetraynoate
  参考文献：
  名称：

  A synthetic route to anandamide analogues carrying a substituent at the terminal carbon and an acetylene group in the end pentyl chain

  摘要：

  A versatile sequence is developed for the synthesis of' anandamide analogues with an acetylene group in the end pentyl chain carrying a substituent at the terminal carbon of the chain. These analogues are important for SAR studies of the endocannabinoid. anandamide. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.05.071

文献信息

• WO2006/44381
  申请人：——

  公开号：——

  公开（公告）日：——
• Cannabinergic Lipid Ligands
  申请人：Makriyannis Alexandros

  公开号：US20090163557A1

  公开（公告）日：2009-06-25

  One aspect of this disclosure relates generally to lipid compounds that exert diverse effects in the endocannabinoid system, such as regulating CB1 and CB2 receptor or moderating other bio-macromolecules within the endocannabinoid system. Some of the compounds showed improved receptor binding affinity, and/or improved receptor subtype selectivity, and improved bio-stability. Some of the compounds exhibit activities to regulate the enzymes that moderate the bio-disposal of endogenous cannabinoids, such as the fatty acid amide hydrolase (FAAH). Some of the compounds exhibit activities to inhibit the anandamide transporter. Other aspects of the invention are pharmaceutical preparations employing these ligands and methods of administering therapeutically effective amounts of the preparations to provide a physiological effect.
• US8202893B2
  申请人：——

  公开号：US8202893B2

  公开（公告）日：2012-06-19
• A synthetic route to anandamide analogues carrying a substituent at the terminal carbon and an acetylene group in the end pentyl chain
  作者：Ramazan Altundas、Anu Mahadevan、Raj K Razdan

  DOI：10.1016/j.tetlet.2004.05.071

  日期：2004.7

  A versatile sequence is developed for the synthesis of' anandamide analogues with an acetylene group in the end pentyl chain carrying a substituent at the terminal carbon of the chain. These analogues are important for SAR studies of the endocannabinoid. anandamide. (C) 2004 Elsevier Ltd. All rights reserved.