(3aR,4S,8aR,8bS)-4-((dimethyl(phenyl)silyl)methyl)hexahydro-[1,3]dioxolo[4,5-a]pyrrolizin-6-one | 1431853-26-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯里西啶类
• 英文名称: (3aR,4S,8aR,8bS)-4-((dimethyl(phenyl)silyl)methyl)hexahydro-[1,3]dioxolo[4,5-a]pyrrolizin-6-one
• 英文别名: (3aR,4S,8aR,8bS)-4-[[dimethyl(phenyl)silyl]methyl]-3a,4,7,8,8a,8b-hexahydro-[1,3]dioxolo[4,5-a]pyrrolizin-6-one
• CAS: 1431853-26-7
• 化学式: C₁₇H₂₃NO₃Si
• 分子量: 317.46
• InChiKey: NYNJCQSXCJUFON-TXCZRRACSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.72
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  三甲基氰硅烷 、 (3aR,4S,8aR,8bS)-4-((dimethyl(phenyl)silyl)methyl)hexahydro-[1,3]dioxolo[4,5-a]pyrrolizin-6-one 在 正丁基锂 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 17.0h， 生成 (3aR,4S,6R,8aR,8bS)-4-((dimethyl(phenyl)silyl)methyl)hexahydro-4H-[1,3]dioxolo[4,5-a]pyrrolizine-6-carbonitrile 、 (3aR,4S,6S,8aR,8bS)-4-((dimethyl(phenyl)silyl)methyl)hexahydro-4H-[1,3]dioxolo[4,5-a]pyrrolizine-6-carbonitrile
  参考文献：
  名称：

  Asymmetric Approach to Hyacinthacines B₁ and B₂

  摘要：

  Naturally occurring hyacinthacines B-1 and B-2 have been prepared from a common, easily available, advanced intermediate. The approach features several highly stereoselective transformations: inter alia, a dichloroketene-enol ether [2 + 2] cycloaddition, a Bruylants alkylation, and an amino-nitrile alkylation-reduction.

  DOI：

  10.1021/jo400386f
• 作为产物：
  描述：

  二甲醇缩甲醛 、 (5S,6R,7S,7aR)-6,7-dihydroxy-5-((dimethyl(phenyl)silyl)methyl)-hexahydropyrrolizin-3-one 在 phosphoric anhydride 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以88%的产率得到(3aR,4S,8aR,8bS)-4-((dimethyl(phenyl)silyl)methyl)hexahydro-[1,3]dioxolo[4,5-a]pyrrolizin-6-one
  参考文献：
  名称：

  Asymmetric Approach to Hyacinthacines B₁ and B₂

  摘要：

  Naturally occurring hyacinthacines B-1 and B-2 have been prepared from a common, easily available, advanced intermediate. The approach features several highly stereoselective transformations: inter alia, a dichloroketene-enol ether [2 + 2] cycloaddition, a Bruylants alkylation, and an amino-nitrile alkylation-reduction.

  DOI：

  10.1021/jo400386f

文献信息

• Asymmetric Approach to Hyacinthacines B₁ and B₂
  作者：Paidi Venkatram Reddy、Julien Smith、Anushree Kamath、Hélène Jamet、Amaël Veyron、Peter Koos、Christian Philouze、Andrew E. Greene、Philippe Delair

  DOI：10.1021/jo400386f

  日期：2013.5.17

  Naturally occurring hyacinthacines B-1 and B-2 have been prepared from a common, easily available, advanced intermediate. The approach features several highly stereoselective transformations: inter alia, a dichloroketene-enol ether [2 + 2] cycloaddition, a Bruylants alkylation, and an amino-nitrile alkylation-reduction.