((2S,3aR,4R,6S,8aR,8bS)-6-(benzyloxymethyl)-2-phenylhexahydro-4H-[1,3]dioxolo[4,5-a]pyrrolizin-4-yl)methanol | 1431853-38-1

• 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,4R,6S,8aR,8bS)-6-(benzyloxymethyl)-2-phenylhexahydro-4H-[1,3]dioxolo[4,5-a]pyrrolizin-4-yl)methanol
• 英文别名: [(2S,3aR,4R,6S,8aR,8bS)-2-phenyl-6-(phenylmethoxymethyl)-4,6,7,8,8a,8b-hexahydro-3aH-[1,3]dioxolo[4,5-a]pyrrolizin-4-yl]methanol
• CAS: 1431853-38-1
• 化学式: C₂₃H₂₇NO₄
• 分子量: 381.472
• InChiKey: CQJRHUAIRZMVRB-PQBVEICXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  51.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ((2S,3aR,4R,6S,8aR,8bS)-6-(benzyloxymethyl)-2-phenylhexahydro-4H-[1,3]dioxolo[4,5-a]pyrrolizin-4-yl)methanol 在 盐酸 、 palladium 10% on activated carbon 、 氢气 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 16.0h， 以89%的产率得到(+)-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,6S,8aR,8bS)-6-(benzyloxymethyl)-4-((dimethyl(phenyl)silyl)methyl)-2-phenylhexahydro-4H-[1,3]dioxolo[4,5-a]pyrrolizine 在 叔丁基过氧化氢 、 四丁基氟化铵 、 potassium hydride 作用下， 以 四氢呋喃 、 癸烷 、 N,N-二甲基甲酰胺 、 mineral oil 、 正戊烷 为溶剂， 反应 1.0h， 以100%的产率得到((2S,3aR,4R,6S,8aR,8bS)-6-(benzyloxymethyl)-2-phenylhexahydro-4H-[1,3]dioxolo[4,5-a]pyrrolizin-4-yl)methanol
  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.