(S)-1,2-heptadecanediol | 185306-38-1

• 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: (S)-1,2-heptadecanediol
• 英文别名: (2S)-heptadecane-1,2-diol
• CAS: 185306-38-1
• 化学式: C₁₇H₃₆O₂
• 分子量: 272.472
• InChiKey: FDEPHESLFILWER-KRWDZBQOSA-N

物化性质

• 沸点：
  365.3±10.0 °C(Predicted)
• 密度：
  0.894±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  19
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-1,2-heptadecanediol 以 甲醇 、 二氯甲烷 为溶剂， 反应 48.0h， 生成 (2S,4S)-2,6-dimethyl-4-pentadecyl-1,3,6,2lambda5-dioxazaphosphocane 2-oxide
  参考文献：
  名称：

  Synthesis of Optically Pure Cyclic Lipoidal Ammonium Salts and Evaluation of Inhibition of Protein Kinase C

  摘要：

  Stereoisomeric cyclic analogues of hexadecylphosphocholine (Miltefosine) and phosphatidylcholine, (2S,4S)-, (2R,4S)-, (2R,4R)-, and (2S,4R)-2,6,6-trimethyl-2-oxo-4-pentadecyl-1,3-dioxa-6-aza-2-phosphacyclooctane bromide (2a-d), and the enantiomers (S)- and (R)-N-(2-hydroxyethyl)-N-(2-hydroxyheptadecyl)-N,N-dimethylammonium iodide ((S)-and (R)-11) were prepared in good overall yields using optically pure glyceraldehyde surrogates as the starting materials. A four-step synthesis of the key intermediates ((S)- and (R)-1-pentadecyloxirane ((S)-and (R)-3) gave overall high optical purity and chemical yields. Approaches to the synthesis of these key intermediates utilizing asymmetric dihydroxylation on 1-pentadecene gave high chemical yields but only modest optical purity. All ammonium salts inhibited protein kinase C with the following values of IC50 (mu M): 2a (105), 2b (109), 2c (121), 2d (113).

  DOI：

  10.1021/jo961365y
• 作为产物：
  描述：

  正十四烷基三苯基溴化膦 在 palladium on activated charcoal 正丁基锂 、 氢气 作用下， 以 四氢呋喃 、 正己烷 、 乙酸乙酯 为溶剂， 20.0 ℃ 、344.74 kPa 条件下， 反应 86.0h， 生成 (S)-1,2-heptadecanediol
  参考文献：
  名称：

  Study of the synthesis of poecillanosine

  摘要：

  The synthesis of poecillanosine, a natural N-hydroxy-N-nitroso-alkylamine compound, was studied. Poecillanosine was shown to be unstable under acidic nitrosation conditions. Only degradation compounds of poecillanosine were obtained under such conditions, however, the O-methyl derivative of poecillanosine was synthesised and confirmed. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.12.059

文献信息

• Study of the synthesis of poecillanosine
  作者：Ming Xian、Brian J. Shuhler

  DOI：10.1016/j.tetlet.2006.12.059

  日期：2007.2

  The synthesis of poecillanosine, a natural N-hydroxy-N-nitroso-alkylamine compound, was studied. Poecillanosine was shown to be unstable under acidic nitrosation conditions. Only degradation compounds of poecillanosine were obtained under such conditions, however, the O-methyl derivative of poecillanosine was synthesised and confirmed. (c) 2006 Elsevier Ltd. All rights reserved.
• Synthesis of Optically Pure Cyclic Lipoidal Ammonium Salts and Evaluation of Inhibition of Protein Kinase C
  作者：M. Patricia Hubieki、Richard D. Gandour、Curtis L. Ashendel

  DOI：10.1021/jo961365y

  日期：1996.1.1

  Stereoisomeric cyclic analogues of hexadecylphosphocholine (Miltefosine) and phosphatidylcholine, (2S,4S)-, (2R,4S)-, (2R,4R)-, and (2S,4R)-2,6,6-trimethyl-2-oxo-4-pentadecyl-1,3-dioxa-6-aza-2-phosphacyclooctane bromide (2a-d), and the enantiomers (S)- and (R)-N-(2-hydroxyethyl)-N-(2-hydroxyheptadecyl)-N,N-dimethylammonium iodide ((S)-and (R)-11) were prepared in good overall yields using optically pure glyceraldehyde surrogates as the starting materials. A four-step synthesis of the key intermediates ((S)- and (R)-1-pentadecyloxirane ((S)-and (R)-3) gave overall high optical purity and chemical yields. Approaches to the synthesis of these key intermediates utilizing asymmetric dihydroxylation on 1-pentadecene gave high chemical yields but only modest optical purity. All ammonium salts inhibited protein kinase C with the following values of IC50 (mu M): 2a (105), 2b (109), 2c (121), 2d (113).