Toluene-4-sulfonic acid (S)-2-(tert-butyl-diphenyl-silanyloxy)-1-[(2R,5R,2'R,5'R)-5'-((R)-1-hydroxy-ethyl)-octahydro-[2,2']bifuranyl-5-yl]-ethyl ester | 474650-04-9

• 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: Toluene-4-sulfonic acid (S)-2-(tert-butyl-diphenyl-silanyloxy)-1-[(2R,5R,2'R,5'R)-5'-((R)-1-hydroxy-ethyl)-octahydro-[2,2']bifuranyl-5-yl]-ethyl ester
• CAS: 474650-04-9
• 化学式: C₃₅H₄₆O₇SSi
• 分子量: 638.898
• InChiKey: YXUUFTDEQSADBS-DLZDITFFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.12
• 重原子数：
  44.0
• 可旋转键数：
  11.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.49
• 拓扑面积：
  91.29
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  Toluene-4-sulfonic acid (S)-2-(tert-butyl-diphenyl-silanyloxy)-1-[(2R,5R,2'R,5'R)-5'-((R)-1-hydroxy-ethyl)-octahydro-[2,2']bifuranyl-5-yl]-ethyl ester 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以85%的产率得到(R)-1-((2R,5R,2'R,5'R)-(R)-5'-Oxiranyl-octahydro-[2,2']bifuranyl-5-yl)-ethanol
  参考文献：
  名称：

  Essential structural factors of acetogenins, potent inhibitors of mitochondrial complex I

  摘要：

  To elucidate the role of the hydrophobic alkyl tail of acetogenins in the inhibitory action, we synthesized an acetogenin derivative possessing the shortest tail (i.e., methyl group) and examined its inhibitory activity against bovine heart mitochondrial complex I. Our results indicated that the alkyl tail, which is one of the common structural features of natural acetogenins, is not an essential structural factor required for the potent inhibition. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00374-8
• 作为产物：
  描述：

  Toluene-4-sulfonic acid (S)-2-(tert-butyl-diphenyl-silanyloxy)-1-((2R,5R,2'R,5'R)-(R)-5'-oxiranyl-octahydro-[2,2']bifuranyl-5-yl)-ethyl ester 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 96.0h， 以95%的产率得到Toluene-4-sulfonic acid (S)-2-(tert-butyl-diphenyl-silanyloxy)-1-[(2R,5R,2'R,5'R)-5'-((R)-1-hydroxy-ethyl)-octahydro-[2,2']bifuranyl-5-yl]-ethyl ester
  参考文献：
  名称：

  Essential structural factors of acetogenins, potent inhibitors of mitochondrial complex I

  摘要：

  To elucidate the role of the hydrophobic alkyl tail of acetogenins in the inhibitory action, we synthesized an acetogenin derivative possessing the shortest tail (i.e., methyl group) and examined its inhibitory activity against bovine heart mitochondrial complex I. Our results indicated that the alkyl tail, which is one of the common structural features of natural acetogenins, is not an essential structural factor required for the potent inhibition. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00374-8