(3S,4R)-(-)-3-methyl-6-phenyl-1-trimethylsilyl-1-hexyn-4-ol

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (3S,4R)-(-)-3-methyl-6-phenyl-1-trimethylsilyl-1-hexyn-4-ol
• 英文别名: (3R,4S)-4-methyl-1-phenyl-6-trimethylsilylhex-5-yn-3-ol
• 化学式: C₁₆H₂₄OSi
• 分子量: 260.451
• InChiKey: IHSMAWYZOWOCNT-GOEBONIOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  苯丙醛 、 (R)-4-trimethylsilyl-3-butyn-2-yl mesylate 在 indium iodide 、 Pd(PPh₃)(OAc)2 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 为溶剂， 反应 2.0h， 以69%的产率得到(3S,4R)-(-)-3-methyl-6-phenyl-1-trimethylsilyl-1-hexyn-4-ol
  参考文献：
  名称：

  Lipase-Mediated Resolution of 4-TMS-3-butyn-2-ol and Use of the Mesylate Derivatives as a Precursor to a Highly Stereoselective Chiral Allenylindium Reagent

  摘要：

  [GRAPHICS]An improved procedure for the resolution of 4-trimethylsilyl-3-butyn-2-ol has been developed. The mesylate derivatives of the resolved alcohols have been found to undergo highly enantio-, regio-, and diastereoselective additions to aldehydes, leading to homopropargylic alcohol adducts.

  DOI：

  10.1021/ol016605x

文献信息

• Preparation of <i>syn</i>-Tertiary Homoallylic Alcohols Utilizing Allenyltitanocenes Generated by Reductive Titanation of γ-Trimethylsilylpropargylic Carbonates
  作者：Yasutaka Yatsumonji、Takenori Sugita、Akira Tsubouchi、Takeshi Takeda

  DOI：10.1021/ol100395n

  日期：2010.5.7

  syn-Tertiary homoallylic alcohols were obtained by the reaction of α-silylallenyltitanocenes generated by the reductive titanation of γ-silylpropargylic carbonates with Cp2Ti[P(OEt)3]2 with ketones and following desilylation and partial hydrogenation. High diastereoselectivity was observed when aromatic and α,β-unsaturated ketones were employed.

  通过将Cp 2 Ti [P（OEt）3 ] 2与酮还原，然后将甲硅烷基化和部分氢化，将γ-甲硅烷基丙炔碳酸酯进行钛化反应而生成的α-甲硅烷基烯丙基噻吩茂烯，可得到顺式叔丁基醇。当使用芳族和α，β-不饱和酮时，观察到高非对映选择性。
• Scope and stereochemical course of the addition of (trimethylsilyl)allenes to ketones and aldehydes. A regiocontrolled synthesis of homopropargylic alcohols
  作者：Rick L. Danheiser、David J. Carini、Carrie A. Kwasigroch

  DOI：10.1021/jo00370a023

  日期：1986.10
• Diastereoselective and Enantioselective Synthesis of Homopropargyl and Allenylcarbinols from Nonracemic Propargyl Mesylates via the Derived Allenyl and Propargyl Trichlorosilanes
  作者：James A. Marshall、Nicholas D. Adams

  DOI：10.1021/jo971853l

  日期：1997.12.1
• Lipase-Mediated Resolution of 4-TMS-3-butyn-2-ol and Use of the Mesylate Derivatives as a Precursor to a Highly Stereoselective Chiral Allenylindium Reagent
  作者：James A. Marshall、Harry R. Chobanian、Mathew M. Yanik

  DOI：10.1021/ol016605x

  日期：2001.10.1

  [GRAPHICS]An improved procedure for the resolution of 4-trimethylsilyl-3-butyn-2-ol has been developed. The mesylate derivatives of the resolved alcohols have been found to undergo highly enantio-, regio-, and diastereoselective additions to aldehydes, leading to homopropargylic alcohol adducts.