erythro-3-chlorohexane-1,2-diol | 113525-01-2

• 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: erythro-3-chlorohexane-1,2-diol
• 英文别名: (2S,3R)-3-chlorohexane-1,2-diol
• CAS: 113525-01-2；113525-02-3；119719-42-5；131424-41-4；137038-54-1
• 化学式: C₆H₁₃ClO₂
• 分子量: 152.621
• InChiKey: ARBGJJZCHGOTTP-RITPCOANSA-N

物化性质

• 沸点：
  279.9±20.0 °C(predicted)
• 密度：
  1.132±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.75
• 重原子数：
  9.0
• 可旋转键数：
  4.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.46
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  erythro-3-chlorohexane-1,2-diol 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 以78%的产率得到(2S,3S)-(-)-3-丙基环氧乙烷甲醇
  参考文献：
  名称：

  A Practical Synthesis of Chiral 3-Chloro-2-hydroxyalkanoates and 2,3-Epoxyalcohols

  摘要：

  DOI：

  10.1016/s0040-4039(00)96187-2
• 作为产物：
  描述：

  Ethyl 3-chloro-2-oxohexanoate 在 磷酸二氢铵 、 sodium tetrahydroborate 、 potassium dihydrogenphosphate 、 葡萄糖 、 magnesium sulfate 、 calcium carbonate 作用下， 以 乙醇 、 水 为溶剂， 反应 74.6h， 生成 erythro-3-chlorohexane-1,2-diol
  参考文献：
  名称：

  Highly enantioselective reduction of 3-chloro-2-oxoalkanoates with fermenting bakers' yeast. A new synthesis of optically active 3-chloro-2-hydroxyalkanoates and glycidic esters

  摘要：

  Reduction of 3-chloro-2-oxoalkanoic esters with fermenting bakers' yeast gave optically active 3-chloro-2-hydroxyalkanoic esters 2 (anti(2S,3R)/syn (2S,3S) = 52:48-90:10) in 50-85% yields with >95% ee except for 43% ee of ethy syn-(2S,3S)-3-chloro-2-hydroxy-4 phenylbutanoate (2j). Compounds 2 were treated with NaOEt to give (E)-(2R,3S)-2,3-epoxyalkanoates 3 in 30-66% yields with 44-64% ee. Optically active 2,3-epoxy alcohols (cis-23, trans-23, and trans-25), key intermediates for the syntheses of (-)-disparlure (4), mosquito pheromone (5), and a component of passion fruit flavor (6), were prepared with more than 86% ee in high yields.

  DOI：

  10.1021/jo00054a036

文献信息

• Highly Regioselective Ring Opening of 2,3-Epoxy Alcohol Methanesulfonates
  作者：Lian-xun Gao、Hitoshi Saitoh、Fei Feng、Akio Murai

  DOI：10.1246/cl.1991.1787

  日期：1991.10

  Reaction of 2,3-epoxy-1-ol methanesulfonates with diethylaluminum chloride or with the mixture of diethylaluminum chloride and diethylamine hydrobromide in dichloromethane gave rise to regioselectively the corresponding 3-chloro- and 3-bromo-1,2-diol 1-methanesulfonates, respectively, in excellent yields.

  将 2,3-环氧-1-醇甲烷磺酸盐与二乙基氯化铝或二乙基氯化铝与氢溴酸二乙胺的混合物在二氯甲烷中反应，可分别得到相应的 3-氯和 3-溴-1,2-二醇 1-甲烷磺酸盐，且产量极高。
• Regioselective ring openings of 2,3-epoxy alcohols with ammonium halides and sodium benzenethiolate supported on zeolite CaY
  作者：Makoto Onaka、Keisuke Sugita、Hidetoyo Takeuchi、Yusuke Izumi

  DOI：10.1039/c39880001173

  日期：——

  Highly regioselective ring openings of 2,3-epoxy alcohols have been performed by use of zeolite-supported ammonium halides or sodium benzenethiolate; the reactivities of these reagents are highly dependent on the conditions of their preparation.

  已经通过使用沸石负载的卤化铵或苯硫醇钠进行了2,3-环氧醇的高度区域选择性的开环。这些试剂的反应性高度依赖于其制备条件。
• Solvent Dependency in Regioselective Ring Openings of 3,4- and 2,3-Epoxy Alcohols with Diethylamine Hydrohalides
  作者：Lian-xun Gao、Akio Murai

  DOI：10.1246/cl.1991.1503

  日期：1991.9

  Titanium-mediated ring openings of 3,4-epoxy-1-ols at the 4-position with diethylamine hydrohalides proceeded efficiently in dichloromethane, while the requisite openings of 2,3-epoxy-1-ols at the 3-position in benzene.

  钛介导的 3,4-epoxy-1-ols 在 4-位与二乙胺氢卤化物的开环在二氯甲烷中有效地进行，而 2,3-epoxy-1-ols 在苯的 3-位进行必要的开环。
• The first C2 selective halide substitution reaction of 2,3-epoxy alcohols by the use of (CH3O)3B–MX (X=I, Br, Cl) system
  作者：Yoshihide Tomata、Minoru Sasaki、Keiji Tanino、Masaaki Miyashita

  DOI：10.1016/j.tetlet.2003.10.001

  日期：2003.12

  The first C2 selective halide substitution reactions of 2,3-epoxy alcohols have been realized by the use of the (CH3O)3B–MX (X=I, Br, Cl) system, which proceed through novel endo-mode epoxide-opening of intramolecular boron chelates to afford the corresponding C2 halohydrin derivatives with high regio- and stereoselectivity.

  通过使用（CH 3 O）3 B–MX（X = I，Br，Cl）系统，实现了第一个2,3-环氧醇的C2选择性卤化物取代反应，该系统通过新型内模环氧化物进行分子内硼螯合物的开环得到相应的具有高区域和立体选择性的C 2卤代醇衍生物。
• Titanium isopropoxide-mediated nucleophilic openings of 2,3-epoxy alcohols. A mild procedure for regioselective ring-opening
  作者：Maurice Caron、K. B. Sharpless

  DOI：10.1021/jo00209a047

  日期：1985.5