(S)-1,1-diethoxypent-2-yn-4-ol | 156129-56-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-1,1-diethoxypent-2-yn-4-ol
• 英文别名: 3-Pentyn-2-ol, 5,5-diethoxy-, (2S)-；(2S)-5,5-diethoxypent-3-yn-2-ol
• CAS: 156129-56-5
• 化学式: C₉H₁₆O₃
• 分子量: 172.224
• InChiKey: NUYIPJRBAIRPDV-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-1,1-diethoxypent-2-yn-4-ol 在 pyridine-SO3 complex 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 4.0h， 以100%的产率得到[(2S)-5,5-diethoxypent-3-yn-2-yl] hydrogen sulfate
  参考文献：
  名称：

  WO2006/76565

  摘要：

  公开号：
• 作为产物：
  描述：

  丙醛二乙基乙缩醛 在 正丁基锂 、 (S)-BINAL-H 、 zinc(II) chloride 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 生成 (S)-1,1-diethoxypent-2-yn-4-ol
  参考文献：
  名称：

  4-Hydroxynon-2-enal, a cytotoxic lipid peroxidation product, and its C5-analog 4-hydroxypent-2-enal: Enantioselective synthesis and stereoanalysis

  摘要：

  A stereoselective synthesis of the lipid peroxidation products 4-hydroxypent-2-enal (1a) and 4-hydroxynon-2-enal (1b) in high optical purity is presented. The configuration of 1a and b was established by Ru(III)-catalyzed oxidative degradation and subsequent stereoanalysis of the resulting alpha-hydroxy acids. It was demonstrated that 1a is configuratively stable under physiological conditions.

  DOI：

  10.1016/s0040-4020(01)81757-9

文献信息

• Enzymatic resolution of the ethyl acetals of (R)- and (S)-4-hydroxyalk-2-ynals
  作者：Pietro Allevi、Mario Anastasia、Francesco Cajone、Pierangela Ciuffreda、Anna M. Sanvito

  DOI：10.1016/s0957-4166(00)80472-3

  日期：1994.1

  4-hydroxyalk-2-ynals diethylacetals have been efficiently resolved by enatioselective acetylation mediated by Pseudomonas fluorescens lipase affording the acetylated (R)-enantiomers in preference, independent of the length and bulk of the alkyl substituent at the carbinol group. Reduction with LiAlH4 of unreacted or acetylated isomers affords the corresponding ethylenic acetals with the hydrogen deriving from the hydride in the beta position in respect to the allylic hydroxyl.
• WO2006/76565
  申请人：——

  公开号：——

  公开（公告）日：——
• 4-Hydroxynon-2-enal, a cytotoxic lipid peroxidation product, and its C5-analog 4-hydroxypent-2-enal: Enantioselective synthesis and stereoanalysis
  作者：Gerhard Bringmann、Michael Gassen、Raphaëlle Lardy

  DOI：10.1016/s0040-4020(01)81757-9

  日期：1994.8

  A stereoselective synthesis of the lipid peroxidation products 4-hydroxypent-2-enal (1a) and 4-hydroxynon-2-enal (1b) in high optical purity is presented. The configuration of 1a and b was established by Ru(III)-catalyzed oxidative degradation and subsequent stereoanalysis of the resulting alpha-hydroxy acids. It was demonstrated that 1a is configuratively stable under physiological conditions.