(3SR,4RS)-3-chloro-5-methyl-1-(trimethylsilyl)hex-1-yn-4-ol

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 卤代醇
• 英文名称: (3SR,4RS)-3-chloro-5-methyl-1-(trimethylsilyl)hex-1-yn-4-ol
• 英文别名: (3R,4S)-4-chloro-2-methyl-6-trimethylsilylhex-5-yn-3-ol
• 化学式: C₁₀H₁₉ClOSi
• 分子量: 218.799
• InChiKey: VLOURYKNIKIHDN-VHSXEESVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.49
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (3SR,4RS)-3-chloro-5-methyl-1-(trimethylsilyl)hex-1-yn-4-ol 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 以97%的产率得到((2S,3S)-3-Isopropyl-oxiranylethynyl)-trimethyl-silane
  参考文献：
  名称：

  Metalation of 3-trimethylsilyl propargyl chloride: A stereoselective access to trans-propargylic oxiranes

  摘要：

  The metalation of 3-trimethylsilyl-1-chloroprop-2-yne and the subsequent reaction with aldehydes affords stereospecifically anti-chlorohydrins which give after treatment with potassium fluoride and NaOH propargylic epoxides with good to excellent yields. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)80023-3
• 作为产物：
  描述：

  (3-chloro-1-propynyl)trimethylsilane 、 异丁醛 在 zinc dibromide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 2.45h， 以75%的产率得到(3SR,4RS)-3-chloro-5-methyl-1-(trimethylsilyl)hex-1-yn-4-ol
  参考文献：
  名称：

  Metallotropic Equilibrium and Configurational Stability of 3-Chloro-1-(trimethylsilyl)propargyl and -allenyl Metals: Comparative Study among Lithium, Titanium, and Zinc

  摘要：

  A comparative study of the metallotropic equilibrium between 1-chloro-3-(trimethylsilyl)propargyl and -allenyl metals was undertaken by means of lithio-, titano-, and zinco-carbenoids. The lithium and zinc species were shown to react mainly in their allenic metallotropic forms, whereas the titanium species proved to react in both its propargylic and allenic forms. The configurational stability of these organometallics was next examined using a modification of the Hoffmann test. In each case, the organometallic was reacted with a chiral enantiopure electrophile. A comparison of the diastereomeric ratios obtained at low and high conversion rates of the reagent allows assessment of its configurational stability. The lithium species thus exhibited a configurational lability at -125 degrees C in Trapp mixture on the time scale of its reaction with (+)-camphor, while the titanium analogue proved to be configurationally stable at -40 degrees C in THF/Et2O on the time scale defined by its reaction with (S)-N-tritylprolinal. In the context of its reaction with the same electrophile, the zinc bromide species was proven to be partially labile from -80 degrees C in THF and its dynamic kinetic resolution was investigated.

  DOI：

  10.1021/om300420q

文献信息

• Preparation of Propargylic Carbenoids and Reactions with Carbonyl Compounds − A Stereoselective Synthesis of Propargylic Halohydrins and Oxiranes
  作者：Fabrice Chemla、Nicolas Bernard、Franck Ferreira、Jean F. Normant

  DOI：10.1002/1099-0690(200109)2001:17<3295::aid-ejoc3295>3.0.co;2-t

  日期：2001.9

  The preparation and the reactivity of the zincioallene 3 is described. This organometallic compound reacts with aldehydes to yield propargylic halohydrins with good diastereoselectivities. These halohydrins can easily be converted into propargylic oxiranes.

  描述了锌基丙二烯 3 的制备和反应性。这种有机金属化合物与醛反应生成具有良好非对映选择性的炔丙基卤代醇。这些卤代醇可以很容易地转化为炔丙基环氧乙烷。