(R)-14-{(2R,5R,2'R,5'R)-5'-[(1S,5S)-1,5-Bis-(tert-butyl-dimethyl-silanyloxy)-undecyl]-octahydro-[2,2']bifuranyl-5-yl}-14-(tert-butyl-dimethyl-silanyloxy)-tetradecanoic acid | 632323-72-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (R)-14-{(2R,5R,2'R,5'R)-5'-[(1S,5S)-1,5-Bis-(tert-butyl-dimethyl-silanyloxy)-undecyl]-octahydro-[2,2']bifuranyl-5-yl}-14-(tert-butyl-dimethyl-silanyloxy)-tetradecanoic acid
• CAS: 632323-72-9
• 化学式: C₅₁H₁₀₄O₇Si₃
• 分子量: 913.639
• InChiKey: VIJBADJJYLOLPI-NEKQTELZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  16.16
• 重原子数：
  61.0
• 可旋转键数：
  31.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.98
• 拓扑面积：
  83.45
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (R)-14-{(2R,5R,2'R,5'R)-5'-[(1S,5S)-1,5-Bis-(tert-butyl-dimethyl-silanyloxy)-undecyl]-octahydro-[2,2']bifuranyl-5-yl}-14-(tert-butyl-dimethyl-silanyloxy)-tetradecanoic acid 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 以79%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：

  (R)-15-{(2R,5R,2'R,5'R)-5'-[(1S,5S)-1,5-Bis-(tert-butyl-dimethyl-silanyloxy)-undecyl]-octahydro-[2,2']bifuranyl-5-yl}-15-(tert-butyl-dimethyl-silanyloxy)-2-oxo-pentadecanoic acid (S)-1-carboxy-ethyl ester 在 2,3-二氨基吡啶 、 lithium hydroxide 作用下， 以 水 、 叔丁醇 为溶剂， 反应 6.17h， 生成 (R)-14-{(2R,5R,2'R,5'R)-5'-[(1S,5S)-1,5-Bis-(tert-butyl-dimethyl-silanyloxy)-undecyl]-octahydro-[2,2']bifuranyl-5-yl}-14-(tert-butyl-dimethyl-silanyloxy)-tetradecanoic acid
  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

• Analogues of cytotoxic squamocin using reliable reactions: new insights into the reactivity and role of the α,β-unsaturated lactone of the annonaceous acetogenins
  作者：Romain A. Duval、Erwan Poupon、Vanessa Romero、Eva Peris、Guy Lewin、Diego Cortes、Ulrich Brandt、Reynald Hocquemiller

  DOI：10.1016/j.tet.2006.04.066

  日期：2006.6

  A small library of squamocin analogues has been prepared and screened biologically (cytotoxicity, inhibition of mitochondrial complex I and complex III). To centre diversity on a crucial part of the molecule (i.e., the alpha.beta-unsaturated lactone), an original and reliable lactone opening reaction has been discovered and exploited among other efficient reactions. (c) 2006 Elsevier Ltd. All rights reserved.