12-Chlorododecanenitrile | 115141-71-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 12-Chlorododecanenitrile
• CAS: 115141-71-4
• 化学式: C₁₂H₂₂ClN
• 分子量: 215.766
• InChiKey: SIFCHZXNYKKOMA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  14
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  12-Chlorododecanenitrile 在 sodium tetrahydroborate 、 sodium methylate 、 nickel dichloride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 6.75h， 生成 十二烷基伯胺
  参考文献：
  名称：

  Desulfurization with nickel and cobalt boride: scope, selectivity, stereochemistry, and deuterium-labeling studies

  摘要：

  A variety of organosulfur compounds containing alkylthio and arylthio groups underwent reductive desulfurization under notably mild conditions when treated with nickel boride, generated in situ from nickel chloride hexahydrate and sodium borohydride in methanol-THF(3:1). Phenyl,chloro, and ester groups are not reduced under these conditions, while iodo, bromo, nitrile, aldehyde, ketone, cyclopropane, and olefinic functions are reduced either completely or partially. Deuterium-labeling studies indicate that the hydrogen that is incorporated into the product originates from both the sodium borohydride and the protic solvent, suggesting the intermediacy of dihydrogen. The epimers 3alpha- and 3beta-(phenylthio)cholestane afforded 3alpha- and 3beta-deuteriocholestane, respectively, demonstrating that the reaction proceeds with retention of configuration. The method may thus be employed for the stereospecific preparation of deuterated products from organosulfur compounds. Arguments are presented in support of a tentative mechanism involving an oxidative addition-reductive elimination sequence via a nickel hydride intermediate.

  DOI：

  10.1021/jo00061a011
• 作为产物：
  描述：

  11-溴-1-十一醇 在 氯化亚砜 、 sodium iodide 作用下， 以 甲醇 、 四氯化碳 、 水 为溶剂， 生成 12-Chlorododecanenitrile
  参考文献：
  名称：

  Desulfurization with nickel and cobalt boride: scope, selectivity, stereochemistry, and deuterium-labeling studies

  摘要：

  A variety of organosulfur compounds containing alkylthio and arylthio groups underwent reductive desulfurization under notably mild conditions when treated with nickel boride, generated in situ from nickel chloride hexahydrate and sodium borohydride in methanol-THF(3:1). Phenyl,chloro, and ester groups are not reduced under these conditions, while iodo, bromo, nitrile, aldehyde, ketone, cyclopropane, and olefinic functions are reduced either completely or partially. Deuterium-labeling studies indicate that the hydrogen that is incorporated into the product originates from both the sodium borohydride and the protic solvent, suggesting the intermediacy of dihydrogen. The epimers 3alpha- and 3beta-(phenylthio)cholestane afforded 3alpha- and 3beta-deuteriocholestane, respectively, demonstrating that the reaction proceeds with retention of configuration. The method may thus be employed for the stereospecific preparation of deuterated products from organosulfur compounds. Arguments are presented in support of a tentative mechanism involving an oxidative addition-reductive elimination sequence via a nickel hydride intermediate.

  DOI：

  10.1021/jo00061a011

文献信息

• METHOD FOR PRODUCING AMIDE COMPOUND
  申请人：Kugimoto Junichi

  公开号：US20130005960A1

  公开（公告）日：2013-01-03

  The present invention relates to a method for producing a high purity, high quality amide compound, particularly, lactam. A first embodiment of the present invention is characterized in that an amount of each of a halide, an aldehyde compound, an alcohol compound and a nitrile compound contained in a solution recycled into an oxime-forming step is controlled to an amount of 0.4 mol % or less based on the ketone as a starting material. A second embodiment of the present invention is characterized in that one or more compounds selected from the group consisting of a ketone, an oxime and an amide compound are purified by hydrogenation and/or crystallization for eliminating impurities containing a double bond. A third embodiment of the present invention is characterized in that a content of impurities having a cyclic bridge structure is controlled by using a cycloalkanone purified by recrystallization.

  本发明涉及一种生产高纯度、高质量酰胺化合物的方法，特别是内酰胺。本发明的第一实施例的特征在于，通过控制溶液中每种卤化物、醛类化合物、醇类化合物和腈类化合物在回收至肟形成步骤中的含量，使其量不超过以酮为起始物的0.4摩尔％。本发明的第二实施例的特征在于，通过氢化和/或结晶净化从酮、肟和酰胺化合物组成的化合物中选择一种或多种，以消除含有双键的杂质。本发明的第三实施例的特征在于，通过使用通过再结晶纯化的环戊酮来控制具有环桥结构的杂质的含量。
• Method for producing amide compound
  申请人：Ube Industries, Ltd.

  公开号：EP2738161A1

  公开（公告）日：2014-06-04

  The present invention relates to a high purity lactam comprising impurities having a cyclic bridge structure in 50 ppm by weight or less and a method for producing the same. The present invention is characterized in that a content of impurities having a cyclic bridge structure is controlled by using a cycloalkanone purified by recrystallization.

  本发明涉及一种高纯度内酰胺，其中具有环桥结构的杂质含量不超过 50ppm （按重量计），还涉及一种生产高纯度内酰胺的方法。本发明的特点是通过使用经重结晶纯化的环烷酮来控制具有环桥结构的杂质含量。
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  公开号：US8816069B2

  公开（公告）日：2014-08-26
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