(3S,4R)-(-)-4-cyclohexyl-3-methyl-1-trimethylsilyl-but-1-yn-4-ol

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3S,4R)-(-)-4-cyclohexyl-3-methyl-1-trimethylsilyl-but-1-yn-4-ol
• 英文别名: (1R,2S)-1-cyclohexyl-2-methyl-4-trimethylsilylbut-3-yn-1-ol
• 化学式: C₁₄H₂₆OSi
• 分子量: 238.445
• InChiKey: HIWJIXZJEDGKON-JSGCOSHPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.44
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 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：

  (R)-4-trimethylsilyl-3-butyn-2-yl mesylate 、 环己烷基甲醛 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75%的产率得到(3S,4R)-(-)-4-cyclohexyl-3-methyl-1-trimethylsilyl-but-1-yn-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

• Generation of allylic and related organozirconiums through a highly effective zirconium—β-alkoxide elimination reaction
  作者：Hisanaka Ito、Takanori Nakamura、Takeo Taguchi、Yuji Hanzawa

  DOI：10.1016/0040-4020(94)01137-o

  日期：1995.4

  Reactions and characterization of allylic and related zirconium reagents (allenic and γ-alkoxyallylic zirconiums) generated by treatment of allylic and/or propargylic ethers with a zirconocene-butene complex (“Cp2Zr”) are described.

  描述了通过用茂茂锆-丁烯配合物（“ Cp 2 Zr”）处理烯丙基和/或炔丙基醚而生成的烯丙基和相关锆试剂（烯丙基和γ-烷氧基烯丙基锆）的反应和表征。
• Diastereoselective Addition of Organocerium(III) Reagents Derived from 3-Substituted Propargyl Bromides to Aldehydes
  作者：Ulrich Groth、Christian Kesenheimer、Jürgen Neidhöfer

  DOI：10.1055/s-2006-947349

  日期：2006.8

  Various cerium allenyl reagents were generated by trans- metallation of allenyl Grignard compounds with CeCl3 and sub- sequent conversion into homopropargylic alcohols by addition to various aliphatic and aromatic aldehydes. The a-acetylenic alcohols were obtained with regioselectivities and diastereoselectivities up to 98% de in favor of the threo-diastereomers.

  各种铈丙二烯基试剂是通过丙二烯基格氏化合物与CeCl3 的金属转移反应生成的，随后通过加入各种脂肪族和芳香族醛转化为高炔丙醇。获得的α-炔醇的区域选择性和非对映选择性高达98%，有利于苏式非对映异构体。
• 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
• ISHIGURO, MASAHARU;IKEDA, NOBUO;YAMAMOTO, HISASHI, J. ORG. CHEM., 1982, 47, N 11, 2225-2227
  作者：ISHIGURO, MASAHARU、IKEDA, NOBUO、YAMAMOTO, HISASHI

  DOI：——

  日期：——