1-(tert-butyldiphenylsilyloxy)-7-methyl-non-8-en-5-ol | 723296-06-8

• 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: 1-(tert-butyldiphenylsilyloxy)-7-methyl-non-8-en-5-ol
• 英文别名: (3S,5S)-9-[tert-butyl(diphenyl)silyl]oxy-3-methylnon-1-en-5-ol
• CAS: 723296-06-8
• 化学式: C₂₆H₃₈O₂Si
• 分子量: 410.672
• InChiKey: IKYSJRKPLIEZEV-PKTZIBPZSA-N

物化性质

• 沸点：
  479.2±45.0 °C(Predicted)
• 密度：
  0.99±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.31
• 重原子数：
  29
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(tert-butyldiphenylsilyloxy)-7-methyl-non-8-en-5-ol 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 palladium on activated charcoal 偶氮二甲酸二异丙酯 、 四丁基氟化铵 、 氢气 、 1-羟基苯并三唑 、 戴斯-马丁氧化剂 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三苯基膦 、 三氟乙酸 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 16.5h， 生成 4-((3S,6R,8R,11R,13R)-3-Benzyl-4,6,8,11-tetramethyl-2,5-dioxo-1-oxa-4-aza-cyclotridec-13-yl)-butyraldehyde
  参考文献：
  名称：

  Total Synthesis of (−)-Spongidepsin

  摘要：

  A convergent and rapid stereoselective synthesis of (-)-spongidepsin has been achieved from the Roche ester in 14 steps with an overall yield of 13%.

  DOI：

  10.1021/ol061029w
• 作为产物：
  描述：

  4-[4-(tert-butyldiphenylsilyloxy)-butyl]-2-methyl-γ-butyrolactone 在 正丁基锂 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 3.5h， 生成 1-(tert-butyldiphenylsilyloxy)-7-methyl-non-8-en-5-ol
  参考文献：
  名称：

  Total Synthesis of (−)-Spongidepsin

  摘要：

  A convergent and rapid stereoselective synthesis of (-)-spongidepsin has been achieved from the Roche ester in 14 steps with an overall yield of 13%.

  DOI：

  10.1021/ol061029w

文献信息

• Boron Carboxylate Catalysis of Homoallylboration
  作者：Gabrielle J. Dugas、Yu-hong Lam、K. N. Houk、Isaac J. Krauss

  DOI：10.1021/jo500599h

  日期：2014.5.16

  Boron tris(trifluoroacetate) is identified as the first effective catalyst for the homoallyl- and homocrotylboration of aldehydes by cyclopropylcarbinylboronates. NMR spectroscopic studies and theoretical calculations of key intermediates and transition states both suggest that a ligand-exchange mechanism, akin to our previously reported PhBCl2-promoted homoallylations, is operative. Our experimental and theoretical results also suggest that the catalytic activity of boron tris(trifluoroacetate) might originate from more facile catalytic turnover of the trifluoroacetate ligands (in agreement with DFT calculations) or from a lower propensity for formation of off-pathway reservoir intermediates (as observed by H-1 NMR). This work shows that carboxylates are viable catalytic ligands for homoallyl- and homocrotylations of carbonyl compounds and opens the door to the development of catalytic asymmetric versions of this transformation.
• Total Synthesis of (−)-Spongidepsin
  作者：Laurent Ferrié,、Sébastien Reymond、Patrice Capdevielle、Janine Cossy

  DOI：10.1021/ol061029w

  日期：2006.8.1

  A convergent and rapid stereoselective synthesis of (-)-spongidepsin has been achieved from the Roche ester in 14 steps with an overall yield of 13%.