(3R,5S)-5-cyclohexyl-3-((R)-1-phenylethyamino)-dihydrofuran-2(3H)-one | 1273328-84-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (3R,5S)-5-cyclohexyl-3-((R)-1-phenylethyamino)-dihydrofuran-2(3H)-one
• 英文别名: (3R,5S)-5-cyclohexyl-3-[[(1R)-1-phenylethyl]amino]oxolan-2-one
• CAS: 1273328-84-9
• 化学式: C₁₈H₂₅NO₂
• 分子量: 287.402
• InChiKey: HEZOKZVDOLYMLA-XYPHTWIQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3R,5S)-5-cyclohexyl-3-((R)-1-phenylethyamino)-dihydrofuran-2(3H)-one 在 sodium tetrahydroborate 、 20 wt% Pd(OH)2/C 、 氢气 作用下， 以 甲醇 、 乙醇 为溶剂， 生成 (1S,3R)-3-amino-1-cyclohexylbutane-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
• 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 作用下， 以 甲醇 、 水 为溶剂， 反应 2.0h， 生成 (3R,5S)-5-cyclohexyl-3-((R)-1-phenylethyamino)-dihydrofuran-2(3H)-one
  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

• Stereodivergent synthesis of cyclic γ-aminobutyric acid – GABA analogues
  作者：Andrej Ďuriš、Dušan Berkeš、Pavol Jakubec

  DOI：10.1016/j.tetlet.2019.01.005

  日期：2019.2

  A novel synthetic route towards two series of enantiomerically pure cyclic analogues of 2,3-cis- and 2,3-trans-γ-aminobutyric acid (GABA) was developed. The route is based on the elongation and stereodivergent manipulation of a readily accessible enantiomerically pure γ-substituted α-aminolactone. The five-step route towards the 2,3-cis-substituted GABA analogues was achieved via straightforward carbon

  提出了一条新的合成路线，该路线指向两个对映体纯的2,3-顺式和2,3-反式-γ-氨基丁酸（GABA）系列环状类似物。该途径基于易于获得的对映体纯的γ-取代的α-氨基内酯的延伸和立体发散操纵。朝向2,3-五步路径顺式-取代的GABA类似物达到通过使用一种非经典Wittig反应，接着化学选择性还原内酯的直接的碳链延长和保护基团的开关。通往2,3-反式的五步路线-取代的GABA类似物利用Horner-Wadsworth-Emmons反应和高度立体选择性的分子内氧杂-Michael加成作为关键的合成操作，延长了相同的氨基内酯。总的来说，这种化学方法允许立体发散地制备两种非对映异构体系列的新型GABA类似物。
• 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.