2,3-二甲基己-5-烯-1,3-二醇 | 102877-74-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 2,3-二甲基己-5-烯-1,3-二醇
• 英文名称: 2,3-dimethylhex-5-ene-1,3-diol
• 英文别名: 2,3-Dimethyl-hex-5-en-1,3-diol
• CAS: 102877-74-7
• 化学式: C₈H₁₆O₂
• 分子量: 144.214
• InChiKey: JNBWUSZGQKCEPC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.94
• 重原子数：
  10.0
• 可旋转键数：
  4.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  40.46
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2,3-二甲基己-5-烯-1,3-二醇 在 双氧水 、 臭氧 作用下， 生成 4-Methylmevalolactone
  参考文献：
  名称：

  Tamura; Takai, Journal of the Agricultural Chemical Society of Japan, 1957, vol. 21, p. 394

  摘要：

  DOI：
• 作为产物：
  描述：

  1--2-methyl-butanon-(3) 在 盐酸 、 乙醚 作用下， 生成 2,3-二甲基己-5-烯-1,3-二醇
  参考文献：
  名称：

  Tamura; Takai, Journal of the Agricultural Chemical Society of Japan, 1957, vol. 21, p. 394

  摘要：

  DOI：

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.