(3aR,4S,6R,8aR,8bS)-4-((dimethyl(phenyl)silyl)methyl)hexahydro-4H-[1,3]dioxolo[4,5-a]pyrrolizine-6-carbonitrile | 1431853-27-8

• 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,6R,8aR,8bS)-4-((dimethyl(phenyl)silyl)methyl)hexahydro-4H-[1,3]dioxolo[4,5-a]pyrrolizine-6-carbonitrile
• 英文别名: (3aR,4S,6R,8aR,8bS)-4-[[dimethyl(phenyl)silyl]methyl]-4,6,7,8,8a,8b-hexahydro-3aH-[1,3]dioxolo[4,5-a]pyrrolizine-6-carbonitrile
• CAS: 1431853-27-8
• 化学式: C₁₈H₂₄N₂O₂Si
• 分子量: 328.486
• InChiKey: XARIUVPMCMMYMU-FXXCCUJSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.08
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  45.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (5S,6R,7S,7aR)-6,7-dihydroxy-5-((dimethyl(phenyl)silyl)methyl)-hexahydropyrrolizin-3-one 在 正丁基锂 、 phosphoric anhydride 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 33.0h， 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

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.