(2RS,4S)-2-oxo-4-chloromethyl-1,3,2-dioxathiolane | 146864-19-9

• 分子结构分类: 有机化合物 - 有机氧化合物 - 有机含氧阴离子化合物
• 英文名称: (2RS,4S)-2-oxo-4-chloromethyl-1,3,2-dioxathiolane
• 英文别名: (S)-4-chloromethyl-1,3,2-dioxathiolane 2-oxide；1-Chlormethylaethylensulfit；(4S)-4-chloromethyl-[1,3,2]dioxathiolane 2-oxide；(4s)-4-Chloromethyl-2-oxo-1,3,2-dioxathiolane；(4S)-4-(chloromethyl)-1,3,2-dioxathiolane 2-oxide
• CAS: 146864-19-9
• 化学式: C₃H₅ClO₃S
• 分子量: 156.59
• InChiKey: RGDJXHLNJJZNGO-ZIBWXETASA-N

物化性质

• 沸点：
  247.2±13.0 °C(Predicted)
• 密度：
  1?+-.0.1 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：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  54.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2RS,4S)-2-oxo-4-chloromethyl-1,3,2-dioxathiolane 在 sodium periodate 、 ruthenium(III) trichloride hydrate 作用下， 以 氯仿 、 水 、 乙腈 为溶剂， 反应 1.0h， 以79%的产率得到(S)-4-chloromethyl-[1,3,2]dioxathiolane 2,2-dioxide
  参考文献：
  名称：

  Application of cyclic sulfates in the synthesis of enantiomers of 1-[3-(4-aryl-piperazin-1-yl)-2-hydroxy-propyl]-pyrrolidin-2-one

  摘要：

  The synthesis of enantiomers of 1-[3-(4-aryl-piperazin-1-yl)-2-hydroxy-propyl]-pyrrolidin-2-one derivatives is described. These enantiomers; were synthesized starting from (R)- or (S)-1-chloro-2,3-dihydroxypropane using relevant cyclic sulfates as chiral intermediates. The enantiomeric purities of the final compounds were in the range of 99.3-100.0%, as determined by high performance liquid chromatography. The final compounds were found to display moderate potency as ligands for alpha(1)-adrenoreceptors. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.01.029
• 作为产物：
  描述：

  (S)-3-氯-1,2-丙二醇 在 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以94%的产率得到(2RS,4S)-2-oxo-4-chloromethyl-1,3,2-dioxathiolane
  参考文献：
  名称：

  A New Practical Synthesis of Ethyl (R)-(-)-4-Cyano-3-hydroxybutyrate From (S)-3-chloro-1,2-propanediol

  摘要：

  (R)-(-)-4-氰基-3-羟基丁酸乙酯((R)-CNHB)的实用化学合成是以(S)-3-氯-1,2-丙二醇为原料完成的，而(S,S)-3-氯-1,2-丙二醇是(S,S)-Salen Co(III)催化环氧氯丙烷水解动力学解析（HKR）产生的主要副产物。新的合成方法证明了有机副产物在阿托伐他汀中间体不对称合成中的有效利用。

  DOI：

  10.2174/157017812802139654

文献信息

• A molecular modelling explanation of the unexpected stereochemistry observed in the alkylation of oxazinone-derived glycine equivalents using 4-chloromethyl-1,3,2-dioxathiolane-2-oxide
  作者：Anna Jakubowska、Łukasz Fijałowski、Alicja Nowaczyk、Grzegorz Żuchowski、Katarzyna Kulig

  DOI：10.1016/j.tetasy.2015.10.021

  日期：2015.12

  The (R)- and (S)-enantiomers of 4-chloromethyl-1,3,2-dioxathiolane-2-oxide were used as 'epoxide-like' synthons in the asymmetric alkylation of the enantiomers of oxazinone-derived glycine equivalents. The configurations of the obtained spiro compounds were easily determined using 20 nuclear Overhauser effect nuclear magnetic resonance experiments. Additionally, the mechanisms of the reactions performed were explained using molecular modelling. The spiro derivatives obtained can also be modified and hydrolysed to their corresponding amino acids, which are derivatives of 1-aminocyclopropane-1 -carboxylic acids. (c) 2015 Elsevier Ltd. All rights reserved.
• ——
  作者：Z. A. Bredikhina、A. V. Pashagin、D. V. Savel"ev、A. A. Bredikhin

  DOI：10.1023/a:1011300921771

  日期：——

  Nonracemic beta -blockers, viz., (S)-propranolol and (S)-timolol, were prepared from (S)-glycidol in three steps consisting in the reaction with SOCl2 followed by the reaction of the resulting (4S)-4-chloromethyl-2-oxo-1,3,2-dioxathiolanes with the corresponding phenol and the final cleavage of (4R)-aryloxymethyl sulfites under the action of amines in DMF.