(8E,10E,14Z,16E)-(3S,4R,5R,6S,7R,13R)-4-(tert-Butyl-dimethyl-silanyloxy)-15-ethyl-3,5,7,9,13-pentamethyl-octadeca-8,10,14,16-tetraen-6-ol | 331814-92-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (8E,10E,14Z,16E)-(3S,4R,5R,6S,7R,13R)-4-(tert-Butyl-dimethyl-silanyloxy)-15-ethyl-3,5,7,9,13-pentamethyl-octadeca-8,10,14,16-tetraen-6-ol
• CAS: 331814-92-7
• 化学式: C₃₁H₅₈O₂Si
• 分子量: 490.886
• InChiKey: KNFKFRPVSPUQFL-NOBNGHMOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.5
• 重原子数：
  34.0
• 可旋转键数：
  14.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  29.46
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (8E,10E,14Z,16E)-(3S,4R,5R,6S,7R,13R)-4-(tert-Butyl-dimethyl-silanyloxy)-15-ethyl-3,5,7,9,13-pentamethyl-octadeca-8,10,14,16-tetraen-6-ol 在 戴斯-马丁氧化剂 、 氟化氢吡啶 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 37.5h， 生成 (8E,10E,14Z,16E)-(3S,4R,5S,7R,13R)-15-Ethyl-4-hydroxy-3,5,7,9,13-pentamethyl-octadeca-8,10,14,16-tetraen-6-one
  参考文献：
  名称：

  Participation of the β-hydroxyketone part for potent cytotoxicity of callystatin A, a spongean polyketide

  摘要：

  The participation of the beta -hydroxyketone part of callystatin A in the potent cytotoxicity was analyzed through the analogue-syntheses and the assessment of their biological potencies. The ketonic carbonyl, the 19-hydroxyl, and the three asymmetric methyl groups located in the beta -hydroxyketone part of callystatin A were revealed to contribute to the cytotoxic potency, respectively. Moreover, the alpha,beta -unsaturated delta -lactone portion was shown to serve as a conclusive functional group for the cytotoxic activity. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00220-0
• 作为产物：
  描述：

  ethyl R-(Z)-2-ethyl-4-methyl-6-O-para-methoxybenzylhex-2-enoate 在 咪唑 、 2,6-二甲基吡啶 、 正丁基锂 、 四溴化碳 、 二异丁基氢化铝 、 氟化氢吡啶 、 二甲基亚砜 、 三苯基膦 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 水 、 甲苯 、 乙腈 为溶剂， 反应 83.5h， 生成 (8E,10E,14Z,16E)-(3S,4R,5R,6S,7R,13R)-4-(tert-Butyl-dimethyl-silanyloxy)-15-ethyl-3,5,7,9,13-pentamethyl-octadeca-8,10,14,16-tetraen-6-ol
  参考文献：
  名称：

  Participation of the β-hydroxyketone part for potent cytotoxicity of callystatin A, a spongean polyketide

  摘要：

  The participation of the beta -hydroxyketone part of callystatin A in the potent cytotoxicity was analyzed through the analogue-syntheses and the assessment of their biological potencies. The ketonic carbonyl, the 19-hydroxyl, and the three asymmetric methyl groups located in the beta -hydroxyketone part of callystatin A were revealed to contribute to the cytotoxic potency, respectively. Moreover, the alpha,beta -unsaturated delta -lactone portion was shown to serve as a conclusive functional group for the cytotoxic activity. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00220-0