tert-butyl({(1S,3R)-3-[(Z)-2-iodovinyl]cyclohexyl}oxy)diphenyl silane | 521274-59-9

• 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: tert-butyl({(1S,3R)-3-[(Z)-2-iodovinyl]cyclohexyl}oxy)diphenyl silane
• 英文别名: tert-butyl-[(1S,3R)-3-[(Z)-2-iodoethenyl]cyclohexyl]oxy-diphenylsilane
• CAS: 521274-59-9
• 化学式: C₂₄H₃₁IOSi
• 分子量: 490.5
• InChiKey: JQAXJAULEVZZPL-DGUOWXTLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.07
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  tert-butyl({(1S,3R)-3-[(Z)-2-iodovinyl]cyclohexyl}oxy)diphenyl silane 在 bis-triphenylphosphine-palladium(II) chloride 、 氟化铵 、 copper(l) iodide 、 三乙基铵阳离子 、 氢氟酸 、 potassium carbonate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.5h， 生成 (1S,3R)-3-[(1Z)-but-1-en-3-ynyl]cyclohexanol
  参考文献：
  名称：

  Total Synthesis of Leustroducsin B

  摘要：

  A convergent total synthesis of leustroducsin B (1), which is known to exhibit a variety of biological activities, was successfully carried out. Notable features of our synthesis include construction of the C8 stereocenter by lipase-mediated desymmetrization of meso-diol 4 (90.2% ee) and preparation of the C9-C11 anti-diol moiety by the addition of alkynylzinc reagent 20 to the aldehyde 19. Furthermore, a new diol protecting group, p-silyloxybenzylidene, was developed for the deprotection from densely functionalized substrates under weakly acidic conditions. The protecting group was easily removed in a two-step procedure ((HF)3.Et3N; AcOH-THF-H2O).

  DOI：

  10.1021/ja0340679
• 作为产物：
  描述：

  benzyl (1R*,5R*)-5-hydroxycyclohex-3-ene-1-carboxylate 在 10% palladium on active carbon 咪唑 、 三乙基硅烷 、 4-二甲氨基吡啶 、 sodium hexamethyldisilazane 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， -78.0~20.0 ℃ 、101.33 kPa 条件下， 反应 14.33h， 生成 tert-butyl({(1S,3R)-3-[(Z)-2-iodovinyl]cyclohexyl}oxy)diphenyl silane
  参考文献：
  名称：

  Total Synthesis of Leustroducsin B

  摘要：

  A convergent total synthesis of leustroducsin B (1), which is known to exhibit a variety of biological activities, was successfully carried out. Notable features of our synthesis include construction of the C8 stereocenter by lipase-mediated desymmetrization of meso-diol 4 (90.2% ee) and preparation of the C9-C11 anti-diol moiety by the addition of alkynylzinc reagent 20 to the aldehyde 19. Furthermore, a new diol protecting group, p-silyloxybenzylidene, was developed for the deprotection from densely functionalized substrates under weakly acidic conditions. The protecting group was easily removed in a two-step procedure ((HF)3.Et3N; AcOH-THF-H2O).

  DOI：

  10.1021/ja0340679