(2R,3R)-1,4-dichloro-2,3-dihydroxybutane | 221467-90-9

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 卤代醇
• 英文名称: (2R,3R)-1,4-dichloro-2,3-dihydroxybutane
• 英文别名: (R,R)-1,4-dichloro-2,3-butanediol；(R,R)-1,4-dichloro-butane-2,3-diol；1,4-dichloro-L-1,4-dideoxy-threitol；(2S,3S)-1,4-Dichlor-butan-2,3-diol；(2R,3R)-1,4-dichlorobutane-2,3-diol
• CAS: 221467-90-9
• 化学式: C₄H₈Cl₂O₂
• 分子量: 159.012
• InChiKey: SAUBRJOIKMVSRU-IMJSIDKUSA-N

物化性质

• 沸点：
  327.8±37.0 °C(Predicted)
• 密度：
  1.405±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  氯丙烯镁 、 (2R,3R)-1,4-dichloro-2,3-dihydroxybutane 在 copper(l) iodide 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 以79%的产率得到(5S,6S)-5,6-dihydroxydeca-1,9-diene
  参考文献：
  名称：

  The synthesis of asimilobin and the correction of its tetrahydrofuran segment's configuration

  摘要：

  A highly efficient synthetic method for the trans/threo/trans- bis-tetrahydrofuran (THF) ring building block was established. The title compound was synthesized in thirteen steps from trans-1,4-dichloro-2-butene via a convergent route with a Wittig reaction as the key step. The absolute configuration of the THF segment of naturally occurring asimilobin should be corrected. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)02577-5
• 作为产物：
  描述：

  (2S)-2-[(2S)-环氧乙烷-2-基]环氧乙烷 在 盐酸 作用下， 以 乙醚 为溶剂， 生成 (2R,3R)-1,4-dichloro-2,3-dihydroxybutane
  参考文献：
  名称：

  Feit,P.W., Chemische Berichte, 1960, vol. 93, p. 116 - 127

  摘要：

  DOI：

文献信息

• Catalytic Asymmetric Dihydroxylation of Aliphatic Olefins with Reusable Resin‐Osmium Tetroxide
  作者：Boyapati M. Choudary、Karangula Jyothi、Sateesh Madhi、M. Lakshmi Kantam

  DOI：10.1002/adsc.200303114

  日期：2003.11

  Asymmetric dihydroxylation of aliphatic olefins to chiral diols with good yields and ees by a heterogeneous Resin-OsO4 catalyst using ferricyanide as cooxidant is disclosed for the first time. The catalyst was recovered quantitatively by simple filtration and reused for several times without significant loss of activity.

  首次公开了使用铁氰化物作为助氧化剂的非均相树脂-OsO 4催化剂将脂肪族烯烃不对称二羟基化为高收率和高收率的手性二醇。通过简单的过滤定量地回收催化剂，并重复使用几次，而活性没有明显损失。
• Asymmetric hydrogenations catalysed by diphosphinite rhodium complexes derived from natural tartaric acid
  作者：Jean Bourson、Laureano Oliveros

  DOI：10.1016/s0022-328x(00)89118-4

  日期：1982.4

  Two chiral diphosphinites, derived from natural tartaric acid, have been prepared and used as ligands for the preparation of two asymmetric hydrogenation catalysts, which were isolated in a crystalline state. After several weeks storage, these catlysts are still effective in the asymmetric hydrogenation of α-acetamido- and α-benzamido-cinnamic acid, citraconic acid, 2-phenyl-1-butene. In the hydrogenation

  已经制备了两种衍生自天然酒石酸的手性二亚膦酸酯，并将其用作制备两种不对称氢化催化剂的配体，所述两种不对称氢化催化剂以结晶状态分离。储存数周后，这些催化剂在α-乙酰氨基-和α-苯甲酰胺基肉桂酸，柠康酸，2-苯基-1-丁烯的不对称氢化中仍然有效。在氨基酸前体的氢化中，光学产率为14-44％。从给定的基底开始，每次两个对映体可通过我们的两种催化剂，它们是这样彼此互补的一个的适当选择而获得。考虑了氢化中各种因素对光学产率的影响。
• Asymmetric dihydroxylation of primary allylic halides and a concise synthesis of (−)-diepoxybutane
  作者：Koen P.M. Vanhessche、Zhi-Min Wang、K.Barry Sharpless

  DOI：10.1016/s0040-4039(00)73212-6

  日期：1994.5

  Tire asymmetric dihydroxylation (AD) of primary allylic halides is described. Enantiomeric excesses range from 40 to 98%. Subsequent base treatment gives epoxy alcohols in high yields. This strategy is further illustrated by the synthesis of (-)-diepoxybutane, an important C-4-chiral building block.
• Becker, Heinrich; Sharpless, K. Barry, Angewandte Chemie, 1996, vol. 108, # 4, p. 447 - 449
  作者：Becker, Heinrich、Sharpless, K. Barry

  DOI：——

  日期：——
• Catalytic Asymmetric Dihydroxylation of Olefins with New Catalysts:  The First Example of Heterogenization of OsO₄²^- by Ion-Exchange Technique
  作者：Boyapati M. Choudary、Naidu S. Chowdari、Mannepalli L. Kantam、Kondapuram V. Raghavan

  DOI：10.1021/ja016101u

  日期：2001.9.1