(3Z)-(4'S)-6-(2',2',5',5'-tetramethyl-<1',3'>dioxolan-4'-yl)-4-trimethylsilanylmethyl-hex-3-en-1-yl acetate | 172958-94-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3Z)-(4'S)-6-(2',2',5',5'-tetramethyl-<1',3'>dioxolan-4'-yl)-4-trimethylsilanylmethyl-hex-3-en-1-yl acetate
• CAS: 172958-94-0
• 化学式: C₁₉H₃₆O₄Si
• 分子量: 356.578
• InChiKey: TWILOAUYMQQTPK-RNIVLKNTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.91
• 重原子数：
  24.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (3Z)-(4'S)-6-(2',2',5',5'-tetramethyl-<1',3'>dioxolan-4'-yl)-4-trimethylsilanylmethyl-hex-3-en-1-yl acetate 在 三氟乙酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 6.0h， 以34%的产率得到(3Z)-(7S)-7,8-dihydroxy-8-methyl-4-trimethylsilanylmethyl-non-3-en-1-yl acetate
  参考文献：
  名称：

  Saponaceolides: Differential cytotoxicity and enantioselective synthesis of the right-hand lactone moiety

  摘要：

  The enantioselective synthesis of the right-hand lactone moiety 5 of saponaceolide B, 2, is described. The mean graph profiles of 5 do not match the characteristic patterns of differential cytotoxicity of saponaceolides A, 1, and B, 2, in the NCI human disease-oriented tumor screening panel, pointing out the need of the entire saponaceolide structure for maintaining the specificity and potency of the antitumor activity. En route to 5 several useful chiral building blocks, such as compounds 6, 10, 19, 27, and 28 were prepared.

  DOI：

  10.1016/0957-4166(95)00371-1
• 作为产物：
  描述：

  (3S)-5-Brom-2,3-isopropylidendioxy-2-methylpentan 在 4-二甲氨基吡啶 、 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) 、 叔丁基锂 、 potassium iodide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 38.33h， 生成 (3Z)-(4'S)-6-(2',2',5',5'-tetramethyl-<1',3'>dioxolan-4'-yl)-4-trimethylsilanylmethyl-hex-3-en-1-yl acetate
  参考文献：
  名称：

  Saponaceolides: Differential cytotoxicity and enantioselective synthesis of the right-hand lactone moiety

  摘要：

  The enantioselective synthesis of the right-hand lactone moiety 5 of saponaceolide B, 2, is described. The mean graph profiles of 5 do not match the characteristic patterns of differential cytotoxicity of saponaceolides A, 1, and B, 2, in the NCI human disease-oriented tumor screening panel, pointing out the need of the entire saponaceolide structure for maintaining the specificity and potency of the antitumor activity. En route to 5 several useful chiral building blocks, such as compounds 6, 10, 19, 27, and 28 were prepared.

  DOI：

  10.1016/0957-4166(95)00371-1