(R)-4-chloromethyl-[1,3,2]dioxathiolane 2-oxide | 146864-18-8

• 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: (R)-4-chloromethyl-[1,3,2]dioxathiolane 2-oxide
• 英文别名: (R)-4-chloromethyl-1,3,2-dioxathiolane 2-oxide；(4R)-4-chloromethyl-[1,3,2]dioxathiolane 2-oxide；(R)-4-chloromethyl-[1,3,2]dioxathiolane-2-oxide；1-Chlormethylethylensulfit；(4R)-4-(chloromethyl)-1,3,2-dioxathiolane 2-oxide
• CAS: 146864-18-8
• 化学式: C₃H₅ClO₃S
• 分子量: 156.59
• InChiKey: RGDJXHLNJJZNGO-DXXKLEEJSA-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：

  (R)-4-chloromethyl-[1,3,2]dioxathiolane 2-oxide 在 ruthenium(III) chloride trihydrate sodium hypochlorite 作用下， 以 氘代氯仿 、 水 为溶剂， 反应 0.25h， 以82.1%的产率得到(R)-4-chloromethyl-1,3,2-dioxathiolane 2,2-dioxide
  参考文献：
  名称：

  [EN] METHOD FOR THE PREPARATION OF SUBSTITUTED OXAZOLIDINONES
  [FR] PROCÉDÉ DE PRÉPARATION D'OXAZOLIDINONES SUBSTITUÉES

  摘要：

  本发明涉及一种制备具有化学式(X)的化合物的方法。此外，还要求单独的反应步骤以及中间体。

  公开号：

  WO2012140061A1
• 作为产物：
  描述：

  (R)-(-)-3-氯-1,2-丙二醇 在 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 以94%的产率得到(R)-4-chloromethyl-[1,3,2]dioxathiolane 2-oxide
  参考文献：
  名称：

  Asymmetric synthesis of l-carnitine from (R)-3-chloro-1,2-propanediol

  摘要：

  A practical chemical synthesis of L-carnitine (1) has been accomplished from (R)-3-chloro-1,2-propanediol ((R)-4), which is a main by-product originated from (R,R)-Salen Co(III) catalyzed hydrolytic kinetic resolution (HKR) of (+/-)-epichlorohydrin. (R)-4 was utilized as a chiral starting material to prepare the key intermediate cyclic sulfite ((R)-5). The new synthetic approach demonstrated an efficient utilization of organic by-product for the asymmetric synthesis of bioactive compounds. (C) 2011 Yun Xu Yang. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

  DOI：

  10.1016/j.cclet.2011.01.007

文献信息

• Application of cyclic sulfates in the synthesis of enantiomers of 1-[3-(4-aryl-piperazin-1-yl)-2-hydroxy-propyl]-pyrrolidin-2-one
  作者：Katarzyna Kulig、Agnieszka Boba、Anna Bielejewska、Magdalena Gorska、Barbara Malawska

  DOI：10.1016/j.tetasy.2009.01.029

  日期：2009.2

  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.
• 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.