(2R*,3R*)-5-phenyl-2,3-dimethyl-4-pentyne-1,3-diol

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2R*,3R*)-5-phenyl-2,3-dimethyl-4-pentyne-1,3-diol
• 英文别名: (2S,3S)-2,3-dimethyl-5-phenylpent-4-yne-1,3-diol
• 化学式: C₁₃H₁₆O₂
• 分子量: 204.269
• InChiKey: WWQZDHWDIZGIKX-WCQYABFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  magnesium,ethynylbenzene,bromide 、 4-羟基-3-甲基-2-丁酮 在 四氯化钛 作用下， 以60%的产率得到(2R*,3R*)-5-phenyl-2,3-dimethyl-4-pentyne-1,3-diol
  参考文献：
  名称：

  格氏试剂在TiCl 4介导的α-甲基-β-甲硅烷氧基酮的烷基化反应中的1,2不对称诱导

  摘要：

  用甲苯中的TiCl 4对α-甲基-β-甲硅烷氧基酮进行金属转移，得到环状螯合配合物，该螯合配合物在较少受阻的一侧从格氏试剂进行高度立体选择性的烷基化反应。

  DOI：

  10.1016/s0040-4039(97)00735-1

文献信息

• Internal Lewis Acid Coordination as a Powerful Tool To Promote Highly Stereoselective Alkylation ofα-Alkyl-β-Hydroxy Ketones with Grignard Reagents
  作者：Giuseppe Bartoli、M. Cristina Bellucci、Marcella Bosco、Enrico Marcantoni、Letizia Sambri

  DOI：10.1002/(sici)1521-3765(19981102)4:11<2154::aid-chem2154>3.0.co;2-o

  日期：1998.11.2

  An efficient and highly diastereoselective protocol is described for the alkylation of beta-hydroxy ketones that contain an a-stereocenter. This method is based on the preliminary transformation of the beta-hydroxy group into a titanium alcoholate by means of the facile transmetalation of the corresponding beta-silyloxy derivative with TiCl4 (Method A) or by reaction of the lithium alcoholate with TiCl4 (Method B). On account of the strong internal coordinating action of the Lewis acid, this intermediate assumes a rigid half-chair conformation with the alpha-alkyl substituent in a pseudoaxial position, This geometrical arrangement facilitates the attack of the entering carbanion on the carbonylic function apposite to the alpha-substituent. The method uses simple Grignard reagents as the alkylating agents and allows the addition of a wide variety of carbon frameworks to the carbonyl function. including primary and secondary alkyl chains, arylic, alkynylic, vinylic, and benzylic moieties, with high efficiency and stereoselectivity.
• 1,2 asymmetric induction in the TiCl4 mediated alkylation of α-methyl-β-silyloxy ketones with Grignard reagents
  作者：Giuseppe Bartoli、Marcella Bosco、Letizia Sambri、Enrico Marcantoni

  DOI：10.1016/s0040-4039(97)00735-1

  日期：1997.5

  Transmetallation of an α-methyl-β-silyloxy ketone with TiCl4 in toluene affords a cyclic chelation complex which undergoes highly stereoselective alkylation from Grignard reagents at the less hindered side.

  用甲苯中的TiCl 4对α-甲基-β-甲硅烷氧基酮进行金属转移，得到环状螯合配合物，该螯合配合物在较少受阻的一侧从格氏试剂进行高度立体选择性的烷基化反应。