threo-4,5-epoxy-4-methyl-2-pentanol | 83134-91-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: threo-4,5-epoxy-4-methyl-2-pentanol
• 英文别名: anti-4,5-Epoxy-4-methyl-2-pentanol；(2R)-1-[(2R)-2-methyloxiran-2-yl]propan-2-ol
• CAS: 83134-91-2
• 化学式: C₆H₁₂O₂
• 分子量: 116.16
• InChiKey: YRDQUARXBVPFEL-PHDIDXHHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  8
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  32.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  threo-4,5-epoxy-4-methyl-2-pentanol 生成 (2R,4R)-2-methylpentane-1,2,4-triol
  参考文献：
  名称：

  BONGINI, A.;CARDILLO, G.;ORENA, M.;PORZI, G.;SANDRI, S., J. ORG. CHEM., 1982, 47, N 24, 4626-4633

  摘要：

  DOI：
• 作为产物：
  描述：

  (4R,6R)-4-(iodomethyl)-4,6-dimethyl-1,3-dioxan-2-one 生成 threo-4,5-epoxy-4-methyl-2-pentanol
  参考文献：
  名称：

  BONGINI, A.;CARDILLO, G.;ORENA, M.;PORZI, G.;SANDRI, S., J. ORG. CHEM., 1982, 47, N 24, 4626-4633

  摘要：

  DOI：

文献信息

• Regio- and stereocontrolled synthesis of epoxy alcohols and triols from allylic and homoallylic alcohols via iodocarbonates
  作者：Alessandro Bongini、Giuliana Cardillo、Mario Orena、Gianni Porzi、Sergio Sandri

  DOI：10.1021/jo00145a004

  日期：1982.11
• Synthesis, Analysis, and Field Activity of Sordidin, a Male-Produced Aggregation Pheromone of the Banana Weevil, Cosmopolites sordidus
  作者：Seetharaman Jayaraman、Isaiah O. Ndiege、Allan C. Oehlschlager、Lilliana M. Gonzalez、Dennis Alpizar、Mario Falles、William J. Budenberg、Peter Ahuya

  DOI：10.1023/b:joec.0000006392.54376.0e

  日期：1997.4

  An efficient synthesis of the diastereoisomers of sordidin (1), a male-produced aggregation pheromone of Cosmopolites sordidus, has been developed from commercially available 4-methylpent-4-en-2-ol (2). Preparation of exo-beta-sordidin (1a) and endo-beta-sordidin (1b) is via the anti epoxide, 4d, which is derived via iodocarbonation of 2, The endo-alpha-sordidin (1c) and exo-alpha-sordidin (1d) are prepared from the corresponding syn epoxide, which is available via stereo-controlled epoxidation of the triisopropylsilyloxy derivative, 3b. Silyloxy derivatives of the epoxides, 4, efficiently alkylate the anions of N-cyclohexyldiethylketimine (6a) and 3-pentanone N,N-dimethylhydrazone (6b). Acidic work-up of these alkylation reactions promotes cyclization to give 1, Gram quantities of 1a-1d, 1a + 1b and 1c + 1d have been prepared by this route. In field tests in a banana plantation in Costa Rica, compounds 1a-1d significantly increased capture rates of standard pseudostem traps. Comparable numbers of adults were attracted to pseudostem traps baited with the major naturally occurring isomers of sordidin 1c + 1d or 1a-1d, Although addition of the minor naturally occurring isomers of sordidin (1a and 1b) to pseudostem traps increased capture rates above controls, these compounds did not increase attraction of pseudostem traps to the same extent as 1a-1d. In comparison tests with conventional pseudostem traps, significantly more adults were trapped in water-containing pitfall traps baited with 1a-1d.