(R)-5-(3-((tert-butyldiphenylsilyl)oxy)propyl)furan-2(5H)-one | 1191043-81-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: (R)-5-(3-((tert-butyldiphenylsilyl)oxy)propyl)furan-2(5H)-one
• 英文别名: (2R)-2-[3-[tert-butyl(diphenyl)silyl]oxypropyl]-2H-furan-5-one
• CAS: 1191043-81-8
• 化学式: C₂₃H₂₈O₃Si
• 分子量: 380.559
• InChiKey: BCQQDALCRQLDAX-LJQANCHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.82
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  5-(tert-butyldiphenylsilyloxy)pentanal 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 L-脯氨酸 、 lithium chloride 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 反应 15.0h， 生成 (R)-5-(3-((tert-butyldiphenylsilyl)oxy)propyl)furan-2(5H)-one 、 (R)-(E)-ethyl 7-((tert-butyldiphenylsilyl)oxy)-4-hydroxyhept-2-enoate
  参考文献：
  名称：

  Organocatalytic sequential α-aminoxylation and cis-Wittig olefination of aldehydes: synthesis of enantiopure γ-butenolides

  摘要：

  A short route to enantiopure gamma-butenolides (up to 99% ee) has been developed from readily available starting materials. The strategy involves a sequential organocatalytic alpha-aminoxylation followed by cis-Wittig olefination of aldehydes. The utility of this protocol has been demonstrated in the asymmetric synthesis of trans-(+)-cognac lactone with high enantiomeric purity. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.02.004

文献信息

• Organocatalytic sequential α-aminoxylation and cis-Wittig olefination of aldehydes: synthesis of enantiopure γ-butenolides
  作者：Dattatray A. Devalankar、Pandurang V. Chouthaiwale、Arumugam Sudalai

  DOI：10.1016/j.tetasy.2012.02.004

  日期：2012.2

  A short route to enantiopure gamma-butenolides (up to 99% ee) has been developed from readily available starting materials. The strategy involves a sequential organocatalytic alpha-aminoxylation followed by cis-Wittig olefination of aldehydes. The utility of this protocol has been demonstrated in the asymmetric synthesis of trans-(+)-cognac lactone with high enantiomeric purity. (C) 2012 Elsevier Ltd. All rights reserved.