3-4-dichlorobenzaldehyde N-[-(3-4-dichlorophenyl)methylidene]hydrazone | 53118-46-0

• 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-dichlorobenzaldehyde N-[-(3-4-dichlorophenyl)methylidene]hydrazone
• 英文别名: (3,4-Dichlor-benzyliden)-azin；1-(3,4-dichlorophenyl)-N-[(3,4-dichlorophenyl)methylideneamino]methanimine
• CAS: 53118-46-0
• 化学式: C₁₄H₈Cl₄N₂
• 分子量: 346.043
• InChiKey: YBSMZQHLLSYRAG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  24.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  丙二酸环(亚)异丙酯 、 3-4-dichlorobenzaldehyde N-[-(3-4-dichlorophenyl)methylidene]hydrazone 在 溶剂黄146 作用下， 反应 4.0h， 以84%的产率得到3,3-dimethyl-7,11-di(3,4-dichlorophenyl)-2,4-dioxaspiro[5,5]undecane-1,5,9-trione
  参考文献：
  名称：

  A new domino autocatalytic reaction leading to polyfunctionalized spiro[5.5]undecanes and dispiro[4.2.5.2]pentadecanes

  摘要：

  描述了一种新颖的烯胺与梅尔德鲁姆酸的多米诺自催化反应。在这一反应中，在酸性条件下成功合成了一系列具有显著非对映选择性的多环螺[5.5]十一烷-1,5,9-三酮和双螺[4.2.5.2]十五烷-9,13-二酮衍生物，最多形成六个新键，同时伴随着烯胺的CN键断裂和梅尔德鲁姆酸的分解，副产物乙酰肼作为新型自催化剂。

  DOI：

  10.1039/b822645h
• 作为产物：
  描述：

  3,4-二氯苯甲醛 在 bismuth(III) chloride 、 肼 作用下， 以 水 为溶剂， 反应 0.02h， 以97%的产率得到3-4-dichlorobenzaldehyde N-[-(3-4-dichlorophenyl)methylidene]hydrazone
  参考文献：
  名称：

  An expeditious synthetic approach towards the synthesis of Bis-Schiff bases (aldazines) using ultrasound

  摘要：

  Aldazines (Bis-Schiff bases) 1-24 were synthesized using aromatic aldehydes (heterocyclic and benzaldehydes) and hydrazine hydrate under reflux using conventional heating and/or via ultrasound irradiation using BiCl3 as catalyst. Ultrasonication conditions with cat. BiCl3 proved to be an effective, environmentally friendly synthetic procedure. This methodology is robust in the presence of electron donating and electron withdrawing groups affording desired products with high yields (>95%) in just a couple of minutes vs. hours using conventional heating. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ultsonch.2013.12.011

文献信息

• The effect of aryl substituents on arylcarbene reactivity
  作者：Hideo Tomioka、Kazuo Tabayashi、Yasuji Ozaki、Yasuji Izawa

  DOI：10.1016/s0040-4020(01)96384-7

  日期：1985.1

  and cyclohexane) and the relative rate of O—H insertion into methanol to stereospecific cyclopropanation of the olefin to C—H insertion into cyclohexane are calculated from the ratios of products and substrates. It is found (i) that the reactivities of the substrates decrease in the order of methanol, olefin and cyclohexane and (ii) that electron-donating substituents generally lead to reaction with

  取代的（p -MeO，p -Me，H，p -Cl，p -Br，m-Br，m-MeO，3,4-Cl 2，p -CO 2 Me，m-CN和p -CN）单苯基卡宾在底物的二元混合物（甲醇，顺式根据产物和底物的比例，计算出-4-甲基-2-戊烯和环己烷的OH插入到甲醇中烯烃的立体定向环丙烷化和OH插入到环己烷中的相对比率。发现（i）底物的反应性按甲醇，烯烃和环己烷的顺序降低，和（ii）供电子取代基通常导致与反应性较高的底物反应，而有利于与反应性较低的底物反应。在吸电子取代基的情况下。这些结果是通过取代基改变单线芳基卡宾的亲电性而不是单线态-三重态平衡的改变来解释的。
• Synthesis and cytotoxic evaluation of some styryl ketones and related compounds
  作者：JR Dimmock、P Kumar、JW Quail、U Pugazhenthi、J Yang、M Chen、RS Reid、TM Allen、GY Kao、SPC Cole、G Batist、J Balzarini、E De Clercq

  DOI：10.1016/0223-5234(96)88227-4

  日期：1995.1

  A number of 1-aryl-4-methyl-1-penten-3-ones 1 were converted to the corresponding Mannich bases 2 and analogues 3. Attempts to form the azines 4 from several members in series 1 led to the isolation of the corresponding pyrazolines 5 or aryl aldehyde azines 6. Replacement of the isopropyl group of a compound in series 1 by methyl and ethyl functions led to ketones that reacted with hydrazine producing the corresponding azines. The Mannich bases displayed greater activity than the precursor ketones towards murine P388 and L1210 leukemia cells as well as to a panel of human tumour cell lines. Certain of the Mannich bases had selective toxicity towards some human tumour cell lines and others to L1210 cells (in contrast to human T lymphocytes). Several drug-resistant cell lines were shown to be free from cross resistance to a number of the Mannich bases.
• Rooney,C.S. et al., Journal of medicinal and pharmaceutical chemistry, 1962, vol. 5, p. 155 - 167
  作者：Rooney,C.S. et al.

  DOI：——

  日期：——
• A new domino autocatalytic reaction leading to polyfunctionalized spiro[5.5]undecanes and dispiro[4.2.5.2]pentadecanes
  作者：Bo Jiang、Wen-Juan Hao、Jin-Peng Zhang、Shu-Jiang Tu、Feng Shi

  DOI：10.1039/b822645h

  日期：——

  A new domino autocatalytic reaction of imines with Meldrum's acid was described. In this reaction, a series of polycyclic spiro[5.5]undecane-1,5,9-trione and dispiro[4.2.5.2]pentadecane-9,13-dione derivatives, with remarkable diastereoselectivity, were successfully synthesized in acidic condition, and up to six new bonds were formed accompanied by the CN bond cleavage of the imines and the decomposition of Meldrum's acid, with by-product of acetohydrazide as a novel autocatalyst.

  描述了一种新颖的烯胺与梅尔德鲁姆酸的多米诺自催化反应。在这一反应中，在酸性条件下成功合成了一系列具有显著非对映选择性的多环螺[5.5]十一烷-1,5,9-三酮和双螺[4.2.5.2]十五烷-9,13-二酮衍生物，最多形成六个新键，同时伴随着烯胺的CN键断裂和梅尔德鲁姆酸的分解，副产物乙酰肼作为新型自催化剂。
• An expeditious synthetic approach towards the synthesis of Bis-Schiff bases (aldazines) using ultrasound
  作者：Khalid M. Khan、Waqas Jamil、Nida Ambreen、Muhammad Taha、Shahnaz Perveen、Guillermo A. Morales

  DOI：10.1016/j.ultsonch.2013.12.011

  日期：2014.5

  Aldazines (Bis-Schiff bases) 1-24 were synthesized using aromatic aldehydes (heterocyclic and benzaldehydes) and hydrazine hydrate under reflux using conventional heating and/or via ultrasound irradiation using BiCl3 as catalyst. Ultrasonication conditions with cat. BiCl3 proved to be an effective, environmentally friendly synthetic procedure. This methodology is robust in the presence of electron donating and electron withdrawing groups affording desired products with high yields (>95%) in just a couple of minutes vs. hours using conventional heating. (C) 2013 Elsevier B.V. All rights reserved.