(1R,3R)-1-(4-methylphenyl)-3-((R)-1-phenylethylamino)butane-1,4-diol | 1273328-90-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1R,3R)-1-(4-methylphenyl)-3-((R)-1-phenylethylamino)butane-1,4-diol
• CAS: 1273328-90-7
• 化学式: C₁₉H₂₅NO₂
• 分子量: 299.413
• InChiKey: LOUAWAPYZUUJKT-ATZDWAIDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.13
• 重原子数：
  22.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  52.49
• 氢给体数：
  3.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (1R,3R)-1-(4-methylphenyl)-3-((R)-1-phenylethylamino)butane-1,4-diol 在 20 wt% Pd(OH)2/C 、 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 20.0~40.0 ℃ 、110.0 kPa 条件下， 生成 (1R,3R)-N-(3-hydroxy-1-hydroxymethyl-3-(4-methylphenyl)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
• 作为产物：
  描述：

  在 盐酸 、 sodium tetrahydroborate 作用下， 以 乙醇 、 水 为溶剂， 反应 4.25h， 生成 (1R,3R)-1-(4-methylphenyl)-3-((R)-1-phenylethylamino)butane-1,4-diol
  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