(S,S)-3,4-epoxy-1,2-butanediol

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S,S)-3,4-epoxy-1,2-butanediol
• 英文别名: 1,2-Anhydrothreitol；(1S)-1-[(2S)-oxiran-2-yl]ethane-1,2-diol
• 化学式: C₄H₈O₃
• 分子量: 104.106
• InChiKey: KRBIHOANUQUSRV-IMJSIDKUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  7
• 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：
  53
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  环氧乙烷-2,3-二甲醇 在 ((2,2'-(1,2-ethanediylbis(nitrilomethylidyne))bis(phenolato))-N,N',O,O')cobalt(III)(1+) 作用下， 以81%的产率得到(S,S)-3,4-epoxy-1,2-butanediol
  参考文献：
  名称：

  Regio- and Enantioselective Cyclization of Epoxy Alcohols Catalyzed by a [CoIII(salen)] Complex

  摘要：

  The intramolecular cyclization of epoxy alcohols was catalyzed with excellent regio- and enantiocontrol by a [CoIII(salen)] complex. High endo selectivity was observed for the enantioselective cyclization of terminal epoxy alcohols [Eq. (a)], while the reaction of meso substrates produced novel cyclic and bicyclic ethers in good yields and high enantiopurity. TBME=tert-butyl methyl ether.

  DOI：

  10.1002/(sici)1521-3773(19990712)38:13/14<2012::aid-anie2012>3.0.co;2-h

文献信息

• Highly Selective Hydrolytic Kinetic Resolution of Terminal Epoxides Catalyzed by Chiral (salen)Co^III Complexes. Practical Synthesis of Enantioenriched Terminal Epoxides and 1,2-Diols
  作者：Scott E. Schaus、Bridget D. Brandes、Jay F. Larrow、Makoto Tokunaga、Karl B. Hansen、Alexandra E. Gould、Michael E. Furrow、Eric N. Jacobsen

  DOI：10.1021/ja016737l

  日期：2002.2.1

  The hydrolytic kinetic resolution (HKR) of terminal epoxides catalyzed by chiral (salen)Co(III) complex 1 x OAc affords both recovered unreacted epoxide and 1,2-diol product in highly enantioenriched form. As such, the HKR provides general access to useful, highly enantioenriched chiral building blocks that are otherwise difficult to access, from inexpensive racemic materials. The reaction has several

  由手性 (salen)Co(III) 配合物 1 x OAc 催化的末端环氧化物的水解动力学拆分 (HKR) 提供了回收的未反应环氧化物和高度对映体富集形式的 1,2-二醇产物。因此，HKR 提供了从廉价的外消旋材料中获得有用的、高度对映体富集的手性结构单元的通用途径，而这些结构单元在其他方面难以获得。从实用的角度来看，该反应具有几个吸引人的特点，包括使用 H(2)O 作为反应物和低负载 (0.2-2.0 mol%) 的可回收、市售催化剂。此外，HKR 显示出非凡的范围，因为可以将各种空间和电子变化的环氧化物分解为 > 或 = 99% ee。相应的 1,2-二醇是使用 0.45 当量的 H(2)O 在良好到高对映体过量中产生的。提供了用于分离高度对映体富集的环氧化物和二醇以及催化剂回收和再循环的有用和通用的协议。HKR 反应的选择性因子 (k(rel)) 通过测量约 ee 的产物 ee 来确定。20%
• Synthetic route to optically-pure metabolites of butadiene, and their chiral GC separation
  作者：David J. Claffey、James A. Ruth

  DOI：10.1016/0040-4039(96)01799-6

  日期：1996.10

  4-epoxybutane-1,2-diol were stereospecifically synthesized in excellent yields, and fully characterized, as part of a study on the stereochemical aspects of butadiene metabolism and toxicity. GC methodology was developed whereby baseline separation of the enantiomeric pairs was achieved.

  3,4-环氧丁烷-1,2-二醇的四种可能的立体异构体以优异的产率立体合成，并进行了充分表征，作为丁二烯代谢和毒性的立体化学研究的一部分。开发了GC方法，从而实现了对映体对的基线分离。
• Regio- and Enantioselective Cyclization of Epoxy Alcohols Catalyzed by a [CoIII(salen)] Complex
  作者：Michael H. Wu、Karl B. Hansen、Eric N. Jacobsen

  DOI：10.1002/(sici)1521-3773(19990712)38:13/14<2012::aid-anie2012>3.0.co;2-h

  日期：1999.7.12

  The intramolecular cyclization of epoxy alcohols was catalyzed with excellent regio- and enantiocontrol by a [CoIII(salen)] complex. High endo selectivity was observed for the enantioselective cyclization of terminal epoxy alcohols [Eq. (a)], while the reaction of meso substrates produced novel cyclic and bicyclic ethers in good yields and high enantiopurity. TBME=tert-butyl methyl ether.