3,4-dichloro-benzal-p-chloraniline | 55327-53-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3,4-dichloro-benzal-p-chloraniline
• 英文别名: 3,4-Dichlor-benzal-p-chlor-anilin；Benzenamine, 4-chloro-N-[(3,4-dichlorophenyl)methylene]-；N-(4-chlorophenyl)-1-(3,4-dichlorophenyl)methanimine
• CAS: 55327-53-2
• 化学式: C₁₃H₈Cl₃N
• 分子量: 284.572
• InChiKey: ANBFACTVRCYBHD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  12.4
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3,4-dichloro-benzal-p-chloraniline 、 5,5-二甲基-1,3-环己二酮 以96%的产率得到2,2'-((3,4-dichlorophenyl)methylene)bis(3-hydroxy-5,5-dimethylcyclohex-2-enone)
  参考文献：
  名称：

  Efficient, Solvent-Free, Microwave-Enhanced Condensation of 5,5-Dimethyl-1,3-cyclohexanedione with Aldehydes and Imines Using LiBr as Inexpensive, Mild Catalyst

  摘要：

  Efficient, solvent-free, microwave-enhanced condensation of 5,5-dimethyl-1,3-cyclohexanedione with aldehydes using LiBr as catalyst affords xanthenediones. Imines gave only bis-5,5-dimethyl-1,3-cyclohexanediones at high power; a slightly longer period gave xanthenediones. In both types of reactions, the products are obtained in very good to excellent yields. The present protocol is inexpensive and ecofriendly.

  DOI：

  10.1080/00397910902987792
• 作为产物：
  描述：

  对氯苯胺 、 3,4-二氯苯甲醛 以 neat (no solvent) 为溶剂， 生成 3,4-dichloro-benzal-p-chloraniline
  参考文献：
  名称：

  取代基对多取代亚苄基苯胺中C═N拉伸振动的影响

  摘要：

  合成了39个3,4'/ 4,3'/ 3,3'-二取代的亚苄基苯胺（XBAYs）样品和52个多取代的XBAYs样品，并记录了它们的红外吸收光谱。根据158个取代的XBAY样品（包括参考文献中的57个4,4'-双取代的XBAY样品和101个合成的取代的XBAY样品）的C═N桥键的拉伸振动频率νC═N，进行了取代基对从4,4'-双取代XBAY到多取代XBAYs的νC═N值的扩展研究。用于量化νC═N的修正方程获得了多取代XBAY的值（如公式（3）所示）。公式（3）表明，对于多取代XBAYs的νC═N值进行定量回归分析，不能忽略Y的激发态取代基常数以及X和X之间的取代基特定的交叉相互作用效应。与等式（1）相比，等式（3）在量化替代XBAY的νC═N值方面具有更广泛的应用和更高的准确性。

  DOI：

  10.1002/poc.3969

文献信息

• Reaction of Imines with 5,5‐Dimethyl‐1, 3‐cyclohexandione
  作者：Liangce Rong、Xiaoyue Li、Haiying Wang、Daqing Shi、Shujiang Tu、Qiya Zhuang

  DOI：10.1080/00397910600640131

  日期：2006.8

  The reaction of imines 1 with 5,5-dimethyl-1,3-cyclohexandione 2 in methanol was investigated. When the reaction was carried out without a catalytic amount of molecular iodine, ring-opening derivatives of xanthenediones 3 were obtained in high yields. On the other hand, when molecular iodine and a catalytic amount of zinc powder were employed as the catalyst, xanthenediones derivatives 4 were obtained with excellent yields.
• Katiyar, Sarvagya S.; Lalithambika, M., Zeitschrift fur Physikalische Chemie (Leipzig), 1982, vol. 263, # 5, p. 961 - 973
  作者：Katiyar, Sarvagya S.、Lalithambika, M.

  DOI：——

  日期：——
• Enantioselective Construction of C3-Multifunctionalization α-Hydroxy-β-amino Pyridines via α-Pyridyl Diazoacetate, Water, and Imines for Drug Hunting
  作者：Jian Xue、Zhengli Luo、Jisheng Huang、Yaqi Deng、Suzhen Dong、Shunying Liu

  DOI：10.1021/acs.orglett.2c03987

  日期：2022.12.30

  An asymmetric catalytic approach for the construction of C3-multifunctionalization α-hydroxy-β-amino pyridines has been reported. The products can be accessed by the modulation of two chiral catalysts independently in high yield and with good enantioselectivity. The method features mild reaction conditions and an excellent functional group tolerance. Biological activity analysis shows that the resulting products have a selective antiosteosarcoma activity on 143B cells.