(E)-(3R,4R,8R)-4-(tert-Butyl-dimethyl-silanyloxy)-8-hydroxy-3,6-dimethyl-undec-5-en-2-one | 614754-84-6

• 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: (E)-(3R,4R,8R)-4-(tert-Butyl-dimethyl-silanyloxy)-8-hydroxy-3,6-dimethyl-undec-5-en-2-one
• 英文别名: (E,3R,4R,8R)-4-[tert-butyl(dimethyl)silyl]oxy-8-hydroxy-3,6-dimethylundec-5-en-2-one
• CAS: 614754-84-6
• 化学式: C₁₉H₃₈O₃Si
• 分子量: 342.594
• InChiKey: MXSDDHOQRJSNFC-XNMQZFBFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  23
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-(3R,4R,8R)-4-(tert-Butyl-dimethyl-silanyloxy)-8-hydroxy-3,6-dimethyl-undec-5-en-2-one 在 吡啶 、 4-二甲氨基吡啶 、 四丁基氟化铵 、 4-甲基苯磺酸吡啶 、 溶剂黄146 、 三乙胺 、 (+)-二异松蒎基氯硼烷 、 tetramethylammonium triacetoxyborohydride 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 乙腈 为溶剂， 反应 120.0h， 生成 (4R,8R,9R,E)-8-hydroxy-6-methyl-9-((7S,9R)-9-(pent-4-enyl)-6,10-dioxaspiro[4,5]decan-7-yl)dec-6-en-4-yl acetate
  参考文献：
  名称：

  Total Synthesis of Dolabelide D

  摘要：

  The first total synthesis of dolabelide D (or of any of the closely related dolabelides) has been achieved with a longest linear sequence of 17 steps. Key features of the synthesis include an application of the catalytic asymmetric silane alcoholysis, the tandem silylformylation-crotylsilylation, and a Brook-like 1,4-carbon to oxygen silyl migration.

  DOI：

  10.1021/ja058692k
• 作为产物：
  描述：

  (E)-(3S,4S,8R)-4-(tert-Butyl-dimethyl-silanyloxy)-3,6-dimethyl-8-triethylsilanyloxy-undeca-1,5-diene 在 氧气 、 copper(l) chloride 、 palladium dichloride 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 (E)-(3R,4R,8R)-4-(tert-Butyl-dimethyl-silanyloxy)-8-hydroxy-3,6-dimethyl-undec-5-en-2-one
  参考文献：
  名称：

  Total Synthesis of Dolabelide D

  摘要：

  The first total synthesis of dolabelide D (or of any of the closely related dolabelides) has been achieved with a longest linear sequence of 17 steps. Key features of the synthesis include an application of the catalytic asymmetric silane alcoholysis, the tandem silylformylation-crotylsilylation, and a Brook-like 1,4-carbon to oxygen silyl migration.

  DOI：

  10.1021/ja058692k

文献信息

• Approach to the Synthesis of Dolabelides A and B:  Fragment Synthesis by Tandem Silylformylation−Crotylsilylation
  作者：Darby R. Schmidt、Peter K. Park、James L. Leighton

  DOI：10.1021/ol035431b

  日期：2003.9.1

  [GRAPHICS]A synthesis of the C(15)-C(30) fragment of Dolabelides A and B has been achieved. The recently developed asymmetric silane alcoholysis and tandem silylformylation-crotylsilylation reactions were used as the key steps to establish the C(23)-C(27) 1,5-syn-diol. In addition, the flexibility of this methodology has been demonstrated with an efficient synthesis of the C(24)-C(25) trisubstituted olefin.
• Total Synthesis of Dolabelide D
  作者：Peter K. Park、Steven J. O'Malley、Darby R. Schmidt、James L. Leighton

  DOI：10.1021/ja058692k

  日期：2006.3.1

  The first total synthesis of dolabelide D (or of any of the closely related dolabelides) has been achieved with a longest linear sequence of 17 steps. Key features of the synthesis include an application of the catalytic asymmetric silane alcoholysis, the tandem silylformylation-crotylsilylation, and a Brook-like 1,4-carbon to oxygen silyl migration.