trans-2,3-epoxy-1-hexanol | 89321-71-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环氧化物
• 英文名称: trans-2,3-epoxy-1-hexanol
• 英文别名: [(2S)-3-propyloxiran-2-yl]methanol
• CAS: 89321-71-1；89395-00-6；90528-62-4；90528-63-5；92418-71-8；94992-76-4；106498-75-3；111003-36-2；136174-00-0
• 化学式: C₆H₁₂O₂
• 分子量: 116.16
• InChiKey: IGRZECZSICIWJA-GDVGLLTNSA-N

物化性质

• 沸点：
  187.1±8.0 °C(Predicted)
• 密度：
  0.993±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  8
• 可旋转键数：
  3
• 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

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S36/37/39
• 危险类别码：
  R36/37/38
• 海关编码：
  2910900090

反应信息

• 作为产物：
  描述：

  反式-2-已烯-1-醇 在 叔丁基过氧化氢 、 Ti(diisopropyl tartrate)(OiPr)2 作用下， 以 二氯甲烷 为溶剂， 以90%的产率得到trans-2,3-epoxy-1-hexanol
  参考文献：
  名称：

  Mechanism of asymmetric epoxidation. 1. Kinetics

  摘要：

  The rate of titanium-tartrate-catalyzed asymmetric epoxidation of allylic alcohols is shown to be first-order in substrate and oxidant, and inverse second order in inhibitor alcohol, under pseudo-first conditions in catalyst. The rate is slowed by substitution of electron-withdrawing substituents on the olefin and varies slightly with solvent, CH2Cl2 being the solvent of choice. Asymmetric induction suffers when the size of the alkyl hydroperoxide is reduced. Kinetic resolution of secondary allylic alcohols is shown to be sensitive to the size of the tartrate ester group and insensitive to the steric nature of inhibitor alcohol. Most importantly, the species containing equimolar amounts of Ti and tartrate is shown to be the most active catalyst in the reaction mixture, mediating reaction at much faster rates that titanium tetraalkoxide alone.

  DOI：

  10.1021/ja00001a018

文献信息

• PROCESS FOR COOXIDIZING ORGANIC COMPOUNDS, PROCESS FOR PRODUCING EPOXY COMPOUNDS AND PROCESS FOR PRODUCING ESTERS OR LACTONES
  申请人：Daicel Chemical Industries, Ltd.

  公开号：EP0990631A1

  公开（公告）日：2000-04-05

  According to the inventive co-oxidation process of organic compounds, (A) a compound selected from (A1) a compound having a non-aromatic ethylenic bond and (A2) a ketone or an alcohol corresponding to the ketone is oxidized by molecular oxygen in the presence of N-hydroxyphthalimide or another imide compound and in the coexistence of (B) a compound oxidizable by the imide compound and oxygen and different from the compound (A). As the compound (B), (a) primary or secondary alcohols (e.g., benzhydrol, cyclohexanol), (b) compounds each having a carbon-hydrogen bond at the adjacent position to an unsaturated bond (e.g., tetralin, ethylbenzene) and the like can be used. According to this process, a corresponding epoxy compound from the compound (A1) having a non-aromatic ethylenic bond, and a corresponding ester or lactone from the ketone or its corresponding alcohol (A2) can be obtained in satisfactory yields.

  根据本发明的有机化合物共氧化工艺，(A)选自(A1)具有非芳香族乙烯键的化合物和(A2)酮或与酮相应的醇的化合物，在 N-羟基邻苯二甲酰亚胺或另一种酰亚胺化合物存在下，在(B)可被酰亚胺化合物和氧氧化且不同于化合物(A)的化合物共存的情况下，被分子氧氧化。作为化合物(B)，可以使用(a)伯醇或仲醇（如二苯甲醇、环己醇），(b)在与不饱和键相邻位置各具有一个碳-氢键的化合物（如四萘、乙苯）等。根据该工艺，可以从具有非芳香族乙烯键的化合物（A1）中得到相应的环氧化合物，并从酮或其相应的醇（A2）中得到相应的酯或内酯，产率令人满意。
• Process for the production of esters or lactones, and process for the production of peroxides
  申请人：DAICEL CHEMICAL INDUSTRIES, LTD.

  公开号：EP1754693A1

  公开（公告）日：2007-02-21

  The present invention relates to a process for the production of esters or lactones, and to a process for the production of peroxides.

  本发明涉及一种生产酯或内酯的工艺，以及一种生产过氧化物的工艺。
• PROCESS FOR COOXIDIZING ORGANIC COMPOUNDS
  申请人：DAICEL CHEMICAL INDUSTRIES, LTD.

  公开号：EP0990631B1

  公开（公告）日：2007-01-24
• US4732853A
  申请人：——

  公开号：US4732853A

  公开（公告）日：1988-03-22
• US6229023B1
  申请人：——

  公开号：US6229023B1

  公开（公告）日：2001-05-08