2-氯-1-(氯甲基)乙基十二烷酸酯 | 7208-96-0

• 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-氯-1-(氯甲基)乙基十二烷酸酯
• 英文名称: 2-chloro-1-(chloromethyl)ethyl dodecanoate
• 英文别名: 2-chloro-1-(chloromethyl)ethyl laurate；1,3-dichloro-2-propyl dodecanoate；1,3-dichloroprop-2-yl dodecanoate；1,3-dichloro-2-propyl laureate；lauric acid-(β,β'-dichloro-isopropyl ester)；Laurinsaeure-(β,β'-dichlor-isopropylester)；1,3-Dichloropropan-2-yl dodecanoate
• CAS: 7208-96-0
• 化学式: C₁₅H₂₈Cl₂O₂
• 分子量: 311.292
• InChiKey: KUFXDARQRCNGOA-UHFFFAOYSA-N

物化性质

• 沸点：
  392.7±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-氯-1-(氯甲基)乙基十二烷酸酯 在 silver(I) nitrite 作用下， 生成 2-羟基-1-(羟基甲基)乙基月桂酸酯
  参考文献：
  名称：

  Thieme, Journal fur praktische Chemie (Leipzig 1954), 1912, vol. <2>85, p. 295

  摘要：

  DOI：
• 作为产物：
  描述：

  1,3-二氯丙醇 在 氯磺酸 作用下， 生成 2-氯-1-(氯甲基)乙基十二烷酸酯
  参考文献：
  名称：

  Thieme, Journal fur praktische Chemie (Leipzig 1954), 1912, vol. <2>85, p. 295

  摘要：

  DOI：

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.
• Synthesis of Allyl Esters of Fatty Acids and Their Ovicidal Effect on Cydia pomonella (L.)
  作者：Marc Escribà、Montserrat Barbut、Jordi Eras、Ramon Canela、Jesús Avilla、Mercè Balcells

  DOI：10.1021/jf900097j

  日期：2009.6.10

  Eight allyl esters of fatty acids were synthesized in moderate to high yields with a novel two-step procedure using glycerol as a starting material. The two-step methodology avoids the use of allyl alcohol. The first step consisted of heating at 80 degrees C for 48 h a 2:1:5 mmol mixture of glycerol, a fatty acid, and chlorotrimethylsilane in a solvent-free medium. The crude compound was then dissolved in butanone and heated at 115 degrees C in the presence of Nal. A tandem Finkelstein rearrangement-elimination reaction occurs, producing the corresponding allyl ester. The activity of these esters against Cydia pomonella (L.) (Lepidoptera: Tortricidae) eggs was tested in the laboratory by topical application of one 0.1 mu L drop. All of the compounds showed a concentration-mortality response and caused 100% mortality at the highest concentration tested (10 mg/mL). There was an inverse relationship between the alkyl chain length and the ovicidal activity of the allyl ester; the LC50 and the LC90 of the two compounds that have the longer alkyl chains were significantly higher than those of the rest of the compounds. The ovicidal and IGR activities of this kind of compound appear to be unprecedented.
• Humnicki, Bulletin de la Societe Chimique de France, 1929, vol. <4>45, p. 281
  作者：Humnicki

  DOI：——

  日期：——
• Gruen, Chemische Berichte, 1910, vol. 43, p. 1290
  作者：Gruen

  DOI：——

  日期：——