3-(4-chlorophenyl)aminocyclohexan-1-one

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 3-(4-chlorophenyl)aminocyclohexan-1-one
• 英文别名: 3-(4-chlorophenylamino)cyclohexanone；3-(4-Chloroanilino)cyclohexan-1-one；3-(4-chloroanilino)cyclohexan-1-one
• 化学式: C₁₂H₁₄ClNO
• 分子量: 223.702
• InChiKey: HBQPWQLUOAQFTO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-环己烯-1-酮 、 对氯苯胺 在 magnesia 作用下， 反应 3.33h， 以96%的产率得到3-(4-chlorophenyl)aminocyclohexan-1-one
  参考文献：
  名称：

  MgO nanoparticles as an efficient and reusable catalyst for aza-Michael reaction

  摘要：

  通过改进的溶胶-凝胶技术制备的MgO纳米颗粒具有较窄的粒径分布。合成的氧化镁纳米颗粒在无溶剂条件下于室温下作为高效催化剂，用于一系列α,β-不饱和羰基化合物和硝基烯烃的氮迈克尔加成反应中，以及胺的加成反应，从而获得高产率的β-氨基羰基和β-硝基胺。该催化剂可回收并在至少五次连续运行中重复使用而不会损失活性。

  DOI：

  10.1007/s13738-013-0338-x

文献信息

• Squaric acid as an impressive organocatalyst for Michael addition in water
  作者：Najmadin Azizi、Elham Saki、Mahtab Edrisi

  DOI：10.1016/j.crci.2011.07.003

  日期：2011.11

  Résumé A simple, green, and environmentally benign protocol for squaric acid (5 mg) catalyst conjugate addition of aromatic amines and thiols to unsaturated carbonyl compounds in water in good to excellent yields is developed. The advantages of low sensitivity toward moisture and oxygen, high tolerance of different functional groups, green reaction media and efficient recyclability make this organocatalyst suitable for both laboratory and industrial scale synthesis of β-substituted carbonyls under very mild conditions.

  简历 开发了一种简单、绿色且对环境友好的方案，利用胡椒酸（5毫克）作为催化剂，在水介质中实现了芳香胺和硫醇对不饱和羰基化合物的共轭加成反应，产率良好至优异。该有机催化剂具有对湿气和氧气低敏感性、对多种官能团高度耐受性、绿色反应介质及高效可回收性等优点，非常适用于在非常温和条件下进行β-取代羰基化合物的实验室及工业规模合成。
• Micellar Solution of Sodium Dodecyl Sulfate (SDS) Catalyzes Facile Michael Addition of Amines and Thiols to ?,?-Unsaturated Ketones in Water under Neutral Conditions
  作者：H. Firouzabadi、N. Iranpoor、A.?A. Jafari

  DOI：10.1002/adsc.200404348

  日期：2005.4

  Sodium dodecyl sulfate (SDS) catalyzes facile Michael additions of amines and thiols to α,β-unsaturated ketones under neutral micellar conditions to afford the corresponding Michael adducts in good to high yields.

  十二烷基硫酸钠（SDS）在中性胶束条件下催化胺和硫醇向α ，β-不饱和酮的容易的迈克尔加成反应，从而以高产率高收率地提供相应的迈克尔加合物。
• An environmentally benign protocol: catalyst-free Michael addition of aromatic amines to α,β-unsaturated ketones in glycerol
  作者：Anguo Ying、Qunhui Zhang、Hongmin Li、Gangfeng Shen、Weizhong Gong、Mingju He

  DOI：10.1007/s11164-012-0575-0

  日期：2013.2

  Glycerol was used as a reaction medium as well as promoter for aza-Michael addition of aromatic amines to electronic deficient α,β-unsaturated ketones. Various aromatic amines can react smoothly with chalcone, 2-cyclohexen-1-one, 2-cyclopenten-1-one, and ethyl vinyl ketone to achieve good to excellent yields in the absence of any catalyst.

  甘油被用作反应介质，同时也是芳香胺与缺电子的α,β-不饱和酮的aza-Michael加成反应的促进剂。多种芳香胺能够顺利地与查尔酮、2-环己烯-1-酮、2-环戊烯-1-酮和乙基乙烯酮反应，在无需任何催化剂的情况下实现优良至极佳的产率。
• Guanidine-based task-specific ionic liquids as catalysts for aza-Michael addition under solvent-free conditions
  作者：Anguo Ying、Ming Zheng、Haidan Xu、Fangli Qiu、Changhua Ge

  DOI：10.1007/s11164-011-0296-9

  日期：2011.10

  An efficient and facile protocol for aza-Michael addition of aliphatic and aromatic amines to electron-deficit alkenes using [TMG][Lac] as catalyst under solvent-free conditions was established.

  建立了在无溶剂条件下使用[TMG] [Lac]作为催化剂，将脂肪族和芳香族胺类氮杂-迈克尔加成至缺电子烯烃的有效而简便的方法。
• Aza-Michael addition of aliphatic or aromatic amines to α,β-unsaturated compounds catalyzed by a DBU-derived ionic liquid under solvent-free conditions
  作者：An-Guo Ying、Luo Liu、Guo-Feng Wu、Gang Chen、Xin-Zhi Chen、Wei-Dong Ye

  DOI：10.1016/j.tetlet.2009.01.123

  日期：2009.4

  A task-specific ionic liquid, 1,8-diazabicyclo[5.4.0]-undec-7-en-8-ium acetate has been successfully used as a catalyst for aza-conjugate addition of aliphatic or aromatic amines to various electron deficient alkenes under solvent-free conditions and at room temperature. The catalyst can be reused for six times without noticeable loss of activity.

  任务特定的离子液体1,8-二氮杂双环[5.4.0]-十一碳-7-烯-8-乙酸乙酸盐已成功地用作将脂肪族或芳香族胺类氮杂共轭加成到各种缺电子烯烃中的催化剂在无溶剂条件和室温下。该催化剂可以重复使用六次，而不会明显降低活性。