(1R,3S)-N-(3-cyclohexyl-3-hydroxy-1-(hydroxymethyl)prop-1-yl)dodecanamide | 1273329-18-2

• 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: (1R,3S)-N-(3-cyclohexyl-3-hydroxy-1-(hydroxymethyl)prop-1-yl)dodecanamide
• 英文别名: N-[(2R,4S)-4-cyclohexyl-1,4-dihydroxybutan-2-yl]dodecanamide
• CAS: 1273329-18-2
• 化学式: C₂₂H₄₃NO₃
• 分子量: 369.588
• InChiKey: ADDAHFNPRDJFNH-RTWAWAEBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  26
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  69.6
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (2R)-4-cyclohexyl-4-oxo-2-{[(1R)-1-phenylethyl]amino}-butanoic acid 在 盐酸 、 sodium tetrahydroborate 、 manganese(II) chloride tetrahydrate 、 20 wt% Pd(OH)2/C 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 水 为溶剂， 反应 2.0h， 生成 (1R,3S)-N-(3-cyclohexyl-3-hydroxy-1-(hydroxymethyl)prop-1-yl)dodecanamide
  参考文献：
  名称：

  Expedient and Practical Synthesis of CERT-Dependent Ceramide Trafficking Inhibitor HPA-12 and Its Analogues

  摘要：

  The practical stereodivergent route to both syn- and anti-diastereomers of 1-substituted 3-aminobutane-1,4-diols based on the crystallization-induced asymmetric transformation (CIAT) approach was completed. This led to the revision of the reported stereochemistry of the first inhibitor of CERT-dependent ceramide trafficking HPA-12 from (R,R)-anti- to the (R,S)-syn-enantiomer. Due to the expeditiousness of production and inexpensive conditions developed, a series of alkyl- and aryl-substituted analogues of HPA-12 is also reported.

  DOI：

  10.1021/ol2001057

文献信息

• Expedient and Practical Synthesis of CERT-Dependent Ceramide Trafficking Inhibitor HPA-12 and Its Analogues
  作者：Andrej Ďuriš、Tomáš Wiesenganger、Daniela Moravčíková、Peter Baran、Jozef Kožíšek、Adam Daïch、Dušan Berkeš

  DOI：10.1021/ol2001057

  日期：2011.4.1

  The practical stereodivergent route to both syn- and anti-diastereomers of 1-substituted 3-aminobutane-1,4-diols based on the crystallization-induced asymmetric transformation (CIAT) approach was completed. This led to the revision of the reported stereochemistry of the first inhibitor of CERT-dependent ceramide trafficking HPA-12 from (R,R)-anti- to the (R,S)-syn-enantiomer. Due to the expeditiousness of production and inexpensive conditions developed, a series of alkyl- and aryl-substituted analogues of HPA-12 is also reported.