(2S,3aR,4S,6S,8aR,8bS)-6-(benzyloxymethyl)-4-((dimethyl(phenyl)silyl)methyl)-2-phenylhexahydro-4H-[1,3]dioxolo[4,5-a]pyrrolizine | 1431853-37-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2S,3aR,4S,6S,8aR,8bS)-6-(benzyloxymethyl)-4-((dimethyl(phenyl)silyl)methyl)-2-phenylhexahydro-4H-[1,3]dioxolo[4,5-a]pyrrolizine
• 英文别名: [(2S,3aR,4S,6S,8aR,8bS)-2-phenyl-6-(phenylmethoxymethyl)-4,6,7,8,8a,8b-hexahydro-3aH-[1,3]dioxolo[4,5-a]pyrrolizin-4-yl]methyl-dimethyl-phenylsilane
• CAS: 1431853-37-0
• 化学式: C₃₁H₃₇NO₃Si
• 分子量: 499.725
• InChiKey: KISORFAXYJPPKK-MBLGCPJISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.52
• 重原子数：
  36
• 可旋转键数：
  8
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  30.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,3aR,4S,6S,8aR,8bS)-6-(benzyloxymethyl)-4-((dimethyl(phenyl)silyl)methyl)-2-phenylhexahydro-4H-[1,3]dioxolo[4,5-a]pyrrolizine 在 盐酸 、 叔丁基过氧化氢 、 palladium 10% on activated carbon 、 四丁基氟化铵 、 氢气 、 potassium hydride 作用下， 以 四氢呋喃 、 癸烷 、 乙醇 、 水 、 N,N-二甲基甲酰胺 、 mineral oil 、 正戊烷 为溶剂， 反应 17.0h， 生成 (+)-hyacinthacine B2
  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：

  (2S,3aR,4S,8aR,8bS)-4-((dimethyl(phenyl)silyl)methyl)-2-phenylhexahydro-4H-[1,3]dioxolo[4,5-a]pyrrolizine-6-carbonitrile 在 sodium tetrahydroborate 、 正丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 为溶剂， 反应 1.75h， 生成 (2S,3aR,4S,6S,8aR,8bS)-6-(benzyloxymethyl)-4-((dimethyl(phenyl)silyl)methyl)-2-phenylhexahydro-4H-[1,3]dioxolo[4,5-a]pyrrolizine
  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.