(3S,5Z)-1-bromo-3-[tert-butyl(dimethyl)silyl]oxy-6-methylnona-5,8-dien-2-one | 905288-17-7

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (3S,5Z)-1-bromo-3-[tert-butyl(dimethyl)silyl]oxy-6-methylnona-5,8-dien-2-one
• CAS: 905288-17-7
• 化学式: C₁₆H₂₉BrO₂Si
• 分子量: 361.395
• InChiKey: QZWFGHCQLOGATG-WVUXNXBLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.25
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3S,5Z)-1-bromo-3-[tert-butyl(dimethyl)silyl]oxy-6-methylnona-5,8-dien-2-one 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 乙醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 19.25h， 生成 (10E,13Z)-(4S,7R,8S,9S,16S)-4,8-Bis-(tert-butyl-dimethyl-silanyloxy)-5,5,7,9,13-pentamethyl-16-(2-methyl-thiazol-4-yl)-oxacyclohexadeca-10,13-diene-2,6-dione
  参考文献：
  名称：

  C-15 Thiazol-4-yl Analogues of (E)-9,10-Didehydroepothilone D:  Synthesis and Cytotoxicity

  摘要：

  [GRAPHICS]The syntheses and biological evaluation of six epothilone D analogues are reported. These side-chain variants of the (E)-9,10-didehydroepothilone scaffold contain C-15 thiazole appendages that are derived from bromomethyl ketone intermediates. Although each of these analogues is less cytotoxic than the parent (E)-9,10-didehydroepothilone D, three maintain IC50 values in the double-digit nanomolar range against both susceptible and resistant cell lines.

  DOI：

  10.1021/ol061087h
• 作为产物：
  描述：

  (5,Z)-3-((tert-butyl)dimethylsiloxy)-6-methylnona-5,8-dien-2-one 在 三氟甲磺酸三甲基硅酯 、 N,N-二异丙基乙胺 、 N-溴代丁二酰亚胺(NBS) 、 碳酸氢钠 作用下， 以 二氯甲烷 、 四氢呋喃 为溶剂， 反应 3.5h， 生成 (3S,5Z)-1-bromo-3-[tert-butyl(dimethyl)silyl]oxy-6-methylnona-5,8-dien-2-one
  参考文献：
  名称：

  C-15 Thiazol-4-yl Analogues of (E)-9,10-Didehydroepothilone D:  Synthesis and Cytotoxicity

  摘要：

  [GRAPHICS]The syntheses and biological evaluation of six epothilone D analogues are reported. These side-chain variants of the (E)-9,10-didehydroepothilone scaffold contain C-15 thiazole appendages that are derived from bromomethyl ketone intermediates. Although each of these analogues is less cytotoxic than the parent (E)-9,10-didehydroepothilone D, three maintain IC50 values in the double-digit nanomolar range against both susceptible and resistant cell lines.

  DOI：

  10.1021/ol061087h

文献信息

• C-15 Thiazol-4-yl Analogues of (<i>E</i>)-9,10-Didehydroepothilone D:  Synthesis and Cytotoxicity
  作者：Brian R. Hearn、Dan Zhang、Yong Li、David C. Myles

  DOI：10.1021/ol061087h

  日期：2006.7.1

  [GRAPHICS]The syntheses and biological evaluation of six epothilone D analogues are reported. These side-chain variants of the (E)-9,10-didehydroepothilone scaffold contain C-15 thiazole appendages that are derived from bromomethyl ketone intermediates. Although each of these analogues is less cytotoxic than the parent (E)-9,10-didehydroepothilone D, three maintain IC50 values in the double-digit nanomolar range against both susceptible and resistant cell lines.