<1R-(1α,4β,5β,6β)> N-<5,6-bis(phenylmethoxy)-4-hydroxy-2-cyclohexen-1-yl>-1,3 benzodioxole-4-hydroxy-5-carboxamide | 153165-91-4

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: <1R-(1α,4β,5β,6β)> N-<5,6-bis(phenylmethoxy)-4-hydroxy-2-cyclohexen-1-yl>-1,3 benzodioxole-4-hydroxy-5-carboxamide
• 英文别名: (1R-(1α,4β,5β,6β)) N-(5,6-bis(phenylmethoxy)-4-hydroxy-2-cyclohexen-1-yl)-1,3 benzodioxole-4-hydroxy-5-carboxamide
• CAS: 153165-91-4
• 化学式: C₂₈H₂₇NO₇
• 分子量: 489.525
• InChiKey: MBSHWYNOKVLLEY-ULDOEVFSSA-N

物化性质

• 沸点：
  652.0±55.0 °C(predicted)
• 密度：
  1.38±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.32
• 重原子数：
  36.0
• 可旋转键数：
  8.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  106.48
• 氢给体数：
  3.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  <1R-(1α,4β,5β,6β)> N-<5,6-bis(phenylmethoxy)-4-hydroxy-2-cyclohexen-1-yl>-1,3 benzodioxole-4-hydroxy-5-carboxamide 在 palladium on activated charcoal 氢气 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 2.0h， 以60%的产率得到<1R-(1α,4β,5β,6β)> N-<2,3,4-tris-(hydroxy)-cyclohexanyl>-1,3 benzodioxole-4-hydroxy-5-carboxamide
  参考文献：
  名称：

  Enantiospecific synthesis and biological evaluation of seco analogues of antitumor amaryllidaceae alkaloids

  摘要：

  Some ''seco'' analogues of Amaryllidaceae alkaloids narciclasine and lycoricidine have been prepared in enantiomerically pure form from D-glucose using Ferrier carbocyclization as the key step. N-acylation of the resulting amines 21, 22, 25 and 26 with several aromatic acids led to amides 31-34 structurally related to narciclasine and lycoricidine. These seco analogues are devoided of biological activity.

  DOI：

  10.1016/s0040-4020(01)87223-9
• 作为产物：
  描述：

  1R-(1β,4α,5β,6β) 4-azido-5,6-bis(phenylmethoxy)-2-cyclohexen-1-ol 在 lithium aluminium tetrahydride 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 4.75h， 生成 <1R-(1α,4β,5β,6β)> N-<5,6-bis(phenylmethoxy)-4-hydroxy-2-cyclohexen-1-yl>-1,3 benzodioxole-4-hydroxy-5-carboxamide
  参考文献：
  名称：

  Enantiospecific synthesis and biological evaluation of seco analogues of antitumor amaryllidaceae alkaloids

  摘要：

  Some ''seco'' analogues of Amaryllidaceae alkaloids narciclasine and lycoricidine have been prepared in enantiomerically pure form from D-glucose using Ferrier carbocyclization as the key step. N-acylation of the resulting amines 21, 22, 25 and 26 with several aromatic acids led to amides 31-34 structurally related to narciclasine and lycoricidine. These seco analogues are devoided of biological activity.

  DOI：

  10.1016/s0040-4020(01)87223-9