tert-butyl(cyclohexa-1,5-dienylmethoxy)diphenylsilane

• 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(cyclohexa-1,5-dienylmethoxy)diphenylsilane
• 英文别名: Tert-butyl-(cyclohexa-1,5-dien-1-ylmethoxy)-diphenylsilane
• 化学式: C₂₃H₂₈OSi
• 分子量: 348.56
• InChiKey: CGUYHFURJVBZRX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.84
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1,5-cis,cis-cyclooctadiene 、 tert-butyl(diphenyl)(2-propynyloxy)silane 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 二氯甲烷 为溶剂， 以51%的产率得到tert-butyl(cyclohexa-1,5-dienylmethoxy)diphenylsilane
  参考文献：
  名称：

  Ring Synthesis by Stereoselective, Methylene-Free Enyne Cross Metathesis

  摘要：

  Tandem enyne metathesis between 1-alkynes and 1,5-cyclooctadiene or all-cis-1,4-polybutadiene resulted in a direct, one-step ring synthesis of cyclohexadienes by methylene-free metathesis. The use of methylene-free metathesis conditions provided apparent Z-selectivity in the intermolecular enyne metathesis step.

  DOI：

  10.1021/ja0476922

文献信息

• Pd-Catalyzed Asymmetric Allylic Etherification Using Chiral Biphenol-Based Diphosphinite Ligands and Its Application for The Formal Total Synthesis of (−)-Galanthamine
  作者：Yang Zang、Iwao Ojima

  DOI：10.1021/jo400355j

  日期：2013.4.19

  A library of novel chiral biphenol-based diphosphinite (BOP) ligands was designed and created. These BOP ligands were applied to a Pd-catalyzed intermolecular allylic etherification reaction, which provided a key intermediate for the formal total synthesis of (−)-galanthamine with 97% ee in 97% yield.

  设计并创建了一种新颖的基于手性双酚的二亚膦酸酯（BOP）配体的库。这些BOP配体被应用于Pd催化的分子间烯丙基醚化反应，该反应为（97）ee的97％收率的（-）-加兰他敏进行正式的全合成提供了关键的中间体。
• Synthesis of 1,3-cyclohexadienes by tandem diene–alkyne metathesis: improved procedure
  作者：Mark D. Middleton、Steven T. Diver

  DOI：10.1016/j.tetlet.2005.04.017

  日期：2005.6

  A practical synthesis of 2-substituted 1,3-cyclohexadienes by the cross enyne metathesis between alkynes and 1,5-hexadiene is reported. The isolation of the 1,3-cyclohexadienes has been hampered by the formation of an inseparable triene by-product. The use of a second consecutive cross alkene metathesis to give water-soluble products allowed removal of this by-product. Using this one-pot procedure, a synthesis of cyclohexadienes from simple starting materials was developed. The procedure was used in a three-step synthesis of a functionalized tetrahydroquinoline using Pd(II)-catalyzed chloroacetoxyiation (Backvall reaction) for cyclohexadiene functionalization. (c) 2005 Elsevier Ltd. All rights reserved.
• 2-SUBSTITUTED-1,3-CYCLOHEXADIENES BY INTERMOLECULAR, METHYLENE-FREE TANDEM ENYNE METATHESIS
  作者：Kulkarni, Amol A、Diver, Steven T.、Shibasaki, Masakatsu、Maki, Keisuke

  DOI：10.15227/orgsyn.083.0200

  日期：——
• Ring Synthesis by Stereoselective, Methylene-Free Enyne Cross Metathesis
  作者：Amol A. Kulkarni、Steven T. Diver

  DOI：10.1021/ja0476922

  日期：2004.7.1

  Tandem enyne metathesis between 1-alkynes and 1,5-cyclooctadiene or all-cis-1,4-polybutadiene resulted in a direct, one-step ring synthesis of cyclohexadienes by methylene-free metathesis. The use of methylene-free metathesis conditions provided apparent Z-selectivity in the intermolecular enyne metathesis step.