2,3-二氯-1-丙基十二烷酸酯 | 118646-55-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 2,3-二氯-1-丙基十二烷酸酯
• 英文名称: 2,3-dichloro-1-propyl dodecanoate
• 英文别名: 2,3-dichloro-1-propyl laurate；lauric acid-(2,3-dichloro-propyl ester)；Laurinsaeure-(2,3-dichlor-propylester)；2,3-di-chloropropyl laurate；2,3-Dichloropropyl dodecanoate
• CAS: 118646-55-2
• 化学式: C₁₅H₂₈Cl₂O₂
• 分子量: 311.292
• InChiKey: WOHLMAITODGALK-UHFFFAOYSA-N

物化性质

• 沸点：
  372.5±22.0 °C(Predicted)
• 密度：
  1.028±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  19
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,3-二氯-1-丙基十二烷酸酯 在 水 作用下， 以 甲基叔丁基醚 为溶剂， 反应 24.0h， 生成 2,3-二氯-1-丙醇
  参考文献：
  名称：

  Biocatalytic preparation of dichloropropyl acrylates. Application to the synthesis of poly(dichloropropyl acrylates)

  摘要：

  The synthesis of dichloropropyl acrylates from dichloropropyl dodecanoates through a transesterification process using diverse commercial lipases and whole cells (fungal resting cells) is presented. The synthesis was carried out in a solvent-free media using a conventional batch system and a packed bed reactor (PBR). The effect of water activity on the process depended on the lipase used. The commercial enzyme CALB (Candida antarctica lipase B immobilized onto a macroporous acrylic resin) showed the best performance as a biocatalyst, achieving a yield of 50% and productivity of 7.2 mu mol min(-1) g(-1) in the batch reactor and 33% and 35.8 mu mol min(-1) g(-1) in the PBR. Finally, polymeric material was prepared by suspension polymerization of the dichloropropyl acrylates synthesized using PBR. Particles with diameters between 170 and 380 mu m were obtained with a yield of 85% after 18 h reaction. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2013.03.005
• 作为产物：
  描述：

  2-氯-1-(氯甲基)乙基十二烷酸酯 反应 1.0h， 生成 2,3-二氯-1-丙基十二烷酸酯
  参考文献：
  名称：

  Biocatalytic preparation of dichloropropyl acrylates. Application to the synthesis of poly(dichloropropyl acrylates)

  摘要：

  The synthesis of dichloropropyl acrylates from dichloropropyl dodecanoates through a transesterification process using diverse commercial lipases and whole cells (fungal resting cells) is presented. The synthesis was carried out in a solvent-free media using a conventional batch system and a packed bed reactor (PBR). The effect of water activity on the process depended on the lipase used. The commercial enzyme CALB (Candida antarctica lipase B immobilized onto a macroporous acrylic resin) showed the best performance as a biocatalyst, achieving a yield of 50% and productivity of 7.2 mu mol min(-1) g(-1) in the batch reactor and 33% and 35.8 mu mol min(-1) g(-1) in the PBR. Finally, polymeric material was prepared by suspension polymerization of the dichloropropyl acrylates synthesized using PBR. Particles with diameters between 170 and 380 mu m were obtained with a yield of 85% after 18 h reaction. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2013.03.005

文献信息

• Combining AlCl3·6H2O and an ionic liquid to prepare chlorohydrin esters from glycerol
  作者：Gemma Villorbina、Albert Tomàs、Marc Escribà、Mireia Oromí-Farrús、Jordi Eras、Mercè Balcells、Ramon Canela

  DOI：10.1016/j.tetlet.2009.03.183

  日期：2009.6

  We describe here the first example in which glycerol has been transformed into chlorohydrin esters using an ionic liquid and hydrated aluminium chloride. The method avoids using Crown-18 ether, which was needed to obtain a similar yield when KCl was used. Alkyl and aryl acids can be used, although yields are very dependent on the carboxylic acid used.

  我们在这里描述第一个例子，其中使用离子液体和水合氯化铝将甘油转化为氯醇酯。该方法避免了使用Crown-18醚，而使用KCl时需要使用Crown-18醚才能获得相似的收率。可以使用烷基和芳基酸，尽管产率非常取决于所用的羧酸。
• Lipase activity and enantioselectivity of whole cells from a wild-type Aspergillius flavus strain
  作者：Carmen Solarte、Edinson Yara-Varón、Jordi Eras、Mercè Torres、Mercè Balcells、Ramon Canela-Garayoa

  DOI：10.1016/j.molcatb.2013.12.005

  日期：2014.2

  This study reports the high enantiomeric preference of whole cell lipase from Aspergillus flavus wild-type that allows the preparation of a chiral secondary alcohol. Whole cells prepared from a wild-type Aspergillus flavus strain were used as biocatalysts to prepare (R)-1-phenylethyl acetate. (R)-1-Phenylethanol was esterified into (R)-1-phenylethyl acetate with a 94.6% enantiomeric excess (ee) within 24h at 40 degrees C and (S)-1-phenylethanol remained in the reaction medium with a >99%ee. Besides, this biocatalyst allows the preparation of ethyl laurate and a mixture of 2-chloro-1-(chloromethyl)ethyl acrylate and 2,3-dichloro-1-propyl acrylate. The ethyl laurate yield was 96%, whereas the synthesis of a mixture of the acrylate regioisomers, 2-chloro-1-(chloromethyl)ethyl acrylate and 2,3-dichloro-1 -propyl acrylate gave similar yields to those obtained using commercial lipases. (C) 2013 Elsevier B.V. All rights reserved.
• Gruen; v.Skopnik, Chemische Berichte, 1909, vol. 42, p. 3753
  作者：Gruen、v.Skopnik

  DOI：——

  日期：——
• US4470843A
  申请人：——

  公开号：US4470843A

  公开（公告）日：1984-09-11