2-chloro-1-dodecen-3-ol | 134857-89-9

• 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: 2-chloro-1-dodecen-3-ol
• 英文别名: 2-Chlorododec-1-en-3-ol
• CAS: 134857-89-9
• 化学式: C₁₂H₂₃ClO
• 分子量: 218.767
• InChiKey: JTLIVISZOAIAQB-UHFFFAOYSA-N

物化性质

• 沸点：
  293.5±15.0 °C(Predicted)
• 密度：
  0.947±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  14
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-chloro-1-dodecen-3-ol 在 二甲基硫 、 水 、 臭氧 作用下， 生成 2-羟基十一烷酸
  参考文献：
  名称：

  1-Chloroalkyl p-tolyl sulfoxides as useful agents for homologation of carbonyl compounds: conversion of carbonyl compounds to .alpha.-hydroxy acids, esters, and amides and .alpha.,.alpha.'-dihydroxy ketones

  摘要：

  One-carbon homologation of carbonyl compounds to alpha-hydroxy acids, esters, and amides by the use of 1-chloroalkyl p-tolyl sulfoxide as a hydroxycarbonyl anion equivalent is reported. Oxidation of the vinyl chlorides, the intermediates of the above-mentioned method, with osmium tetraoxide gives alpha,alpha'-dihydroxy ketones which are found in biologically active natural products such as cortisone and adriamycin.

  DOI：

  10.1021/jo00013a011
• 作为产物：
  描述：

  2-chloro-2-(4-methylphenyl)sulfinyldodecan-3-ol 以 xylene 为溶剂， 反应 0.33h， 以96%的产率得到2-chloro-1-dodecen-3-ol
  参考文献：
  名称：

  1-Chloroalkyl p-tolyl sulfoxides as useful agents for homologation of carbonyl compounds: conversion of carbonyl compounds to .alpha.-hydroxy acids, esters, and amides and .alpha.,.alpha.'-dihydroxy ketones

  摘要：

  One-carbon homologation of carbonyl compounds to alpha-hydroxy acids, esters, and amides by the use of 1-chloroalkyl p-tolyl sulfoxide as a hydroxycarbonyl anion equivalent is reported. Oxidation of the vinyl chlorides, the intermediates of the above-mentioned method, with osmium tetraoxide gives alpha,alpha'-dihydroxy ketones which are found in biologically active natural products such as cortisone and adriamycin.

  DOI：

  10.1021/jo00013a011

文献信息

• 1-Chloroalkyl<i>p</i>-Tolyl Sulfoxides as Acetylide Anion Equivalent: A Novel Synthesis Including Asymmetric Synthesis of Propargylic Alcohols from Carbonyl Compounds
  作者：Tsuyoshi Satoh、Yasumasa Hayashi、Koji Yamakawa

  DOI：10.1246/bcsj.64.2153

  日期：1991.7

  Addition of the carbanion of 1-chloroalkyl p-tolyl sulfoxide to carbonyl compounds gave the adducts, which were heated in refluxing toluene or xylene to give vinyl chlorides in high overall yield. Dehydrochlorination of the vinyl chlorides with excess n-BuLi afforded propargylic alcohols in high yields. Asymmetric synthesis of both enantiomers of the propargylic alcohols was realized using optically

  将 1-氯烷基对甲苯基亚砜的碳负离子加成到羰基化合物中得到加合物，将其在回流的甲苯或二甲苯中加热以得到高总收率的氯乙烯。用过量的正丁基锂对氯乙烯进行脱氯化氢，以高产率得到炔丙醇。炔丙醇的两种对映异构体的不对称合成是使用光学活性的 1-氯烷基对甲苯基亚砜和醛实现的。
• Nucleophilic Ring-Opening of Chlorooxiranes: A New Synthesis of α-Hydroxy α′-Substituted Ketones from Carbonyl Compounds and 1-Chloroalkyl<i>p</i>-Tolyl Sulfoxides
  作者：Tsuyoshi Satoh、Asako Ogura、Youko Ikeda、Koji Yamakawa

  DOI：10.1246/bcsj.64.1582

  日期：1991.5

  The addition of 1-chloroalkyl p-tolyl sulfoxides to carbonyl compounds gave adducts which were then converted to chlorooxiranes in two steps with good overall yields. The treatment of the chlorooxiranes with various nucleophiles gave α-hygroxy α′-substituted ketones or α-hydroxy ketones in good yields.

  1-chloroalkyl p-tolyl sulfoxides 与羰基化合物的加成反应产生了加合物，然后通过两个步骤将其转化为氯环氧乙烷，总产率很高。用各种亲核剂处理氯环氧乙烷，可以得到α-羟基α′-取代酮或α-羟基酮，收率很高。
• SATOH, TSUYOSHI;ONDA, KEN-ICHI;YAMAKAWA, KOJI, J. ORG. CHEM., 56,(1991) N3, C. 4129-4134
  作者：SATOH, TSUYOSHI、ONDA, KEN-ICHI、YAMAKAWA, KOJI

  DOI：——

  日期：——