[(1R)-13-(1H-benzimidazol-2-yl)-1-[(2R,5R)-5-[(2R,5R)-5-[(1S,5S)-1,5-bis[[tert-butyl(dimethyl)silyl]oxy]undecyl]oxolan-2-yl]oxolan-2-yl]tridecoxy]-tert-butyl-dimethylsilane | 632323-75-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: [(1R)-13-(1H-benzimidazol-2-yl)-1-[(2R,5R)-5-[(2R,5R)-5-[(1S,5S)-1,5-bis[[tert-butyl(dimethyl)silyl]oxy]undecyl]oxolan-2-yl]oxolan-2-yl]tridecoxy]-tert-butyl-dimethylsilane
• CAS: 632323-75-2
• 化学式: C₅₇H₁₀₈N₂O₅Si₃
• 分子量: 985.751
• InChiKey: QMNVEMALRCHZKY-NJOWKQKFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  17.8
• 重原子数：
  67
• 可旋转键数：
  34
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  74.8
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [(1R)-13-(1H-benzimidazol-2-yl)-1-[(2R,5R)-5-[(2R,5R)-5-[(1S,5S)-1,5-bis[[tert-butyl(dimethyl)silyl]oxy]undecyl]oxolan-2-yl]oxolan-2-yl]tridecoxy]-tert-butyl-dimethylsilane 在 amberlyst-15(R) 作用下， 以 甲醇 为溶剂， 反应 7.0h， 以95%的产率得到
  参考文献：
  名称：

  Semisynthesis of heterocyclic analogues of squamocin, a cytotoxic annonaceous acetogenin, by an unusual oxidative decarboxylation reaction

  摘要：

  In addition to two expected pyrazin derivatives, two imidazole analogues of squamocin I have been semisynthetised from squamocin derived alpha-ketoesters/alpha-ketoacid, via an unusual condensation-oxidative decarboxylation reaction with 1,2 diamines in presence of acetic acid and oxygen as the key step. Some of these analogues exhibited potent, although significantly reduced cytotoxicities relatively to squamocin 1. In addition, benzimidazole 8 possessed in comparison with the natural acetogenin some interesting cell cycle effects. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00306-7
• 作为产物：
  描述：

  (5S)-3-[(13R)-13-[(2R,5R)-5-[(2R,5R)-5-[(1S,5S)-1,5-二羟基十一烷基]四氢呋喃-2-基]四氢呋喃-2-基]-13-羟基十三烷基]-5-甲基-5H-呋喃-2-酮 在 吡啶 、 4-二甲氨基吡啶 、 ruthenium trichloride 、 lithium hydroxide 、 sodium periodate 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 水 为溶剂， 反应 6.25h， 生成 [(1R)-13-(1H-benzimidazol-2-yl)-1-[(2R,5R)-5-[(2R,5R)-5-[(1S,5S)-1,5-bis[[tert-butyl(dimethyl)silyl]oxy]undecyl]oxolan-2-yl]oxolan-2-yl]tridecoxy]-tert-butyl-dimethylsilane
  参考文献：
  名称：

  Semisynthesis of heterocyclic analogues of squamocin, a cytotoxic annonaceous acetogenin, by an unusual oxidative decarboxylation reaction

  摘要：

  In addition to two expected pyrazin derivatives, two imidazole analogues of squamocin I have been semisynthetised from squamocin derived alpha-ketoesters/alpha-ketoacid, via an unusual condensation-oxidative decarboxylation reaction with 1,2 diamines in presence of acetic acid and oxygen as the key step. Some of these analogues exhibited potent, although significantly reduced cytotoxicities relatively to squamocin 1. In addition, benzimidazole 8 possessed in comparison with the natural acetogenin some interesting cell cycle effects. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00306-7

文献信息

• Semisynthesis of heterocyclic analogues of squamocin, a cytotoxic annonaceous acetogenin, by an unusual oxidative decarboxylation reaction
  作者：R Duval

  DOI：10.1016/s0968-0896(03)00306-7

  日期：2003.8.5

  In addition to two expected pyrazin derivatives, two imidazole analogues of squamocin I have been semisynthetised from squamocin derived alpha-ketoesters/alpha-ketoacid, via an unusual condensation-oxidative decarboxylation reaction with 1,2 diamines in presence of acetic acid and oxygen as the key step. Some of these analogues exhibited potent, although significantly reduced cytotoxicities relatively to squamocin 1. In addition, benzimidazole 8 possessed in comparison with the natural acetogenin some interesting cell cycle effects. (C) 2003 Elsevier Ltd. All rights reserved.