(2S^*,3S^*)-1-Acetoxy-2,3-epoxyhexane | 170209-06-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2S^*,3S^*)-1-Acetoxy-2,3-epoxyhexane
• 英文别名: (+/-)-(E)-3-Propyloxiranemethanol acetate；(2S,3S)-1-Acetoxy-2,3-epoxyhexane；(3-propyloxiran-2-yl)methyl acetate
• CAS: 170209-06-0
• 化学式: C₈H₁₄O₃
• 分子量: 158.197
• InChiKey: QRBSPUUMRYNXNH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S^*,3S^*)-1-Acetoxy-2,3-epoxyhexane 在 偶氮二异丁腈 三正丁基氢锡 、 magnesium iodide 作用下， 以 乙醚 、 甲苯 为溶剂， 反应 6.0h， 生成 1-乙酰氧基-2-己醇
  参考文献：
  名称：

  Regioselective opening of epoxy alcohols: mild chemo- and stereoselective preparation of iodohydrins and 1,2-diols

  摘要：

  Several 2,3-epoxy alcohols have been opened, at -60-degrees-C, with MgI2, leading to the corresponding 3-iodo 1,2-diols with a high level of regio- and chemoselectivity. The iodohydrins can be reduced "in situ", by means of nBu3SnH, to the corresponding 1,2-diols. The chemo-, regio-, and stereocontrol of the reaction makes the method of wide use. Furthermore, epoxy alcohol derivatives (acetyl, benzyl, or TBMS) still maintain a strong preference for C-3 attack of the nucleophile. The experimental data strongly suggest that a metal (Mg) centered chelate is formed throughout the reaction, which gives rise to the regioselective delivery of the iodide ion.

  DOI：

  10.1021/jo00021a045
• 作为产物：
  描述：

  (2S,3S)-(-)-3-丙基环氧乙烷甲醇 以98%的产率得到(2S^*,3S^*)-1-Acetoxy-2,3-epoxyhexane
  参考文献：
  名称：

  Regioselective opening of epoxy alcohols: mild chemo- and stereoselective preparation of iodohydrins and 1,2-diols

  摘要：

  Several 2,3-epoxy alcohols have been opened, at -60-degrees-C, with MgI2, leading to the corresponding 3-iodo 1,2-diols with a high level of regio- and chemoselectivity. The iodohydrins can be reduced "in situ", by means of nBu3SnH, to the corresponding 1,2-diols. The chemo-, regio-, and stereocontrol of the reaction makes the method of wide use. Furthermore, epoxy alcohol derivatives (acetyl, benzyl, or TBMS) still maintain a strong preference for C-3 attack of the nucleophile. The experimental data strongly suggest that a metal (Mg) centered chelate is formed throughout the reaction, which gives rise to the regioselective delivery of the iodide ion.

  DOI：

  10.1021/jo00021a045

文献信息

• Concomitant Epoxide Deoxygenation and Deacetylation of Glycidyl Acetates Induced by Telluride Ion
  作者：Donald C. Dittmer、Yanzhi Zhang、Robert P. Discordia

  DOI：10.1021/jo00084a016

  日期：1994.3

  Treatment of glycidyl acetates with telluride ion (Te2-) produced by reduction of elemental Te with LiEt(3)BH yields allylic alcohols by loss of the epoxide oxygen atom and the acetyl group from the ester. If the glycidyl acetate is disubstituted at C-3, a rearrangement to an isomeric allylic alcohol competes with the deoxygenation-deacetylation. Triethylborane, a byproduct in the reduction of Te, is believed to play an important role as a Lewis acid since when it is absent or removed by addition of fluoride ion the reaction is extremely slow.
• Ghelfi, Franco; Grandi, Romano; Pagnoni, Ugo M., Gazzetta Chimica Italiana, 1995, vol. 125, # 5, p. 215 - 218
  作者：Ghelfi, Franco、Grandi, Romano、Pagnoni, Ugo M.

  DOI：——

  日期：——
• Regioselective opening of epoxy alcohols: mild chemo- and stereoselective preparation of iodohydrins and 1,2-diols
  作者：Carlo Bonini、Giuliana Righi、Giovanni Sotgiu

  DOI：10.1021/jo00021a045

  日期：1991.10

  Several 2,3-epoxy alcohols have been opened, at -60-degrees-C, with MgI2, leading to the corresponding 3-iodo 1,2-diols with a high level of regio- and chemoselectivity. The iodohydrins can be reduced "in situ", by means of nBu3SnH, to the corresponding 1,2-diols. The chemo-, regio-, and stereocontrol of the reaction makes the method of wide use. Furthermore, epoxy alcohol derivatives (acetyl, benzyl, or TBMS) still maintain a strong preference for C-3 attack of the nucleophile. The experimental data strongly suggest that a metal (Mg) centered chelate is formed throughout the reaction, which gives rise to the regioselective delivery of the iodide ion.