<4-Nitro-benzyliden>-<3-chlor-anilin> | 10480-21-4

• 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: <4-Nitro-benzyliden>-<3-chlor-anilin>
• 英文别名: 3-Chlor-N-<4-nitro-benzyliden>-anilin；N-<4-Nitro-benzyliden>-3-chlor-anilin；m-Chlor(p-nitrobenzyliden)anilin；(4-Nitro-benzyliden)-(3-chlor-anilin)；Benzenamine, 3-chloro-N-[(4-nitrophenyl)methylene]-；N-(3-chlorophenyl)-1-(4-nitrophenyl)methanimine
• CAS: 10480-21-4
• 化学式: C₁₃H₉ClN₂O₂
• 分子量: 260.68
• InChiKey: ITRPQIGCYZACJJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  18
• 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：
  58.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5,7-dimethoxy-2,2,4-trimethyl-1,2-dihydroquinoline 、 <4-Nitro-benzyliden>-<3-chlor-anilin> 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以90%的产率得到
  参考文献：
  名称：

  以1,2-二氢喹啉为亲二烯体的前驱物的分步控制的Povarov型反应：螺环联双四氢喹啉和功能化的1,2-二氢喹啉的直接合成

  摘要：

  开发了一种新颖的Povarov型反应，可直接合成具有容易获得的1,2-DHQ（1,2-二氢喹啉）和芳香亚胺的新型螺双四氢喹啉。可以在第一阶段在布朗斯台德酸催化剂下选择性地终止反应，以方便地提供相应的官能化的1,2-DHQ。

  DOI：

  10.1021/acs.orglett.6b03330
• 作为产物：
  描述：

  对硝基苯甲醛 、 3-氯苯胺 反应 0.83h， 生成 <4-Nitro-benzyliden>-<3-chlor-anilin>
  参考文献：
  名称：

  Mechanochemical milling promoted solvent-free imino Diels–Alder reaction catalyzed by FeCl₃: diastereoselective synthesis of cis-2,4-diphenyl-1,2,3,4-tetrahydroquinolines

  摘要：

  通过FeCl3促进的无溶剂Diels–Alder反应，在球磨条件下，利用现场生成的亚胺与苯乙烯，对Cis-2,4-二苯基-1,2,3,4-四氢喹啉进行了对映选择性合成。

  DOI：

  10.1039/c4ra05252h

文献信息

• Component match in rhodium catalyzed three-component reactions of ethyl diazoacetate, H2O and aryl imines: a highly diastereoselective one-step synthesis of β-aryl isoserine derivatives
  作者：Zhenqiu Guo、Taoda Shi、Jun Jiang、Liping Yang、Wenhao Hu

  DOI：10.1039/b915013g

  日期：——

  Water and ethyl diazoacetate were found to be matched components for generating highly reactive nucleophilic oxonium ylide in the presence of a dirhodium acetate catalyst. Simultaneous trapping of the oxonium ylide intermediate with aryl imines gave β-aryl isoserine derivatives with high diastereoselectivity.

  发现水和重氮乙酸乙酯是在乙酸二铑催化剂存在下生成高反应性亲核氧鎓叶立德的匹配组分。同时捕获氧鎓叶立德中间体与芳基亚胺得到具有高非对映选择性的β-芳基异丝氨酸衍生物。
• 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.
• Triazolines. XXIX. 1,5-diaryl-Δ²-1,2,3-triazolines as aphicides: Mechanism of action via aziridine formation
  作者：Pankaja K. Kadaba

  DOI：10.1002/ps.2780420407

  日期：1994.12

  AbstractThe aphicidal activity of 21 different 1,5‐diphenyl‐Δ2‐1,2,3‐triazolines, conveniently prepared utilizing the catalytic effect of water on the 1,3‐cyclo‐addition of diazomethane to Schiff bases in aqueous dioxane, was evaluated. Triazolines bearing an o‐Cl substituent on the C‐phenyl, either alone (4) or in combination with a m‐ and/or a p‐substituent on the N‐phenyl (14, 15, 17 and 18), showed significant activity, with a combined m‐, p‐ substitution on the N‐phenyl the most effective (17 and 18). While an o‐Cl substituent led to greater activity than an o‐NO2 group, the introduction of an additional p‐Cl substituent on the C‐phenyl eliminated activity (21).The aphicidal activity of triazoline 18 was found to be dependent on the presence of UV light. Since fluorescent lighting used in the testing procedure contains UV light and since triazolines undergo photolysis when exposed to UV light to yield aziridines, it was logical to conclude that the aphicidal activity of the triazolines was, in fact, derived from the aziridines formed during the testing procedure. This mechanism of action was confirmed by preparing the aziridines 22, 23 and 24 corresponding to the active triazolines 14, 15 and 18, and showing that they possessed aphicidal activity equal to or better than that of the triazolines, and by the activity observed in several other structurally related aziridine analogues (25–28). Unlike aziridinyl phosphorous compounds, the aziridines described here are not mutagenic in the Ames assay and thus afford a safer class of pesticides.
• Mechanochemical milling promoted solvent-free imino Diels–Alder reaction catalyzed by FeCl₃: diastereoselective synthesis of cis-2,4-diphenyl-1,2,3,4-tetrahydroquinolines
  作者：Ya-Jun Tan、Ze Zhang、Fang-Jian Wang、Hao-Hao Wu、Qing-Hai Li

  DOI：10.1039/c4ra05252h

  日期：——

  Cis-2,4-diphenyl-1,2,3,4-tetrahydroquinolines were diastereoselectively synthesized by FeCl₃-promoted solvent-free Diels–Alder reaction of in situ generated imine with styrene under ball milling.

  通过FeCl3促进的无溶剂Diels–Alder反应，在球磨条件下，利用现场生成的亚胺与苯乙烯，对Cis-2,4-二苯基-1,2,3,4-四氢喹啉进行了对映选择性合成。
• Step-Controlled Povarov-Type Reaction with 1,2-Dihydroquinolines as Precursors of Dienophiles: Direct Synthesis of Spirocyclic Bi-tetrahydroquinolines and Functionalized 1,2-Dihydroquinolines
  作者：Xuwen Ren、Guangxun Li、Jin Huang、Weidong Wang、Yongpo Zhang、Guomin Xing、Chunyan Gao、Gang Zhao、Jinzhong Zhao、Zhuo Tang

  DOI：10.1021/acs.orglett.6b03330

  日期：2017.1.6

  A novel Povarov-type reaction for straightforward synthesis of novel spiro bi-tetrahydroquinolines with readily available 1,2-DHQs (1,2-dihydroquinolines) and aromatic imines was developed. The reaction could be selectively stopped at the first stage under a Brønsted acid catalyst to afford the corresponding functionalized 1,2-DHQs conveniently.

  开发了一种新颖的Povarov型反应，可直接合成具有容易获得的1,2-DHQ（1,2-二氢喹啉）和芳香亚胺的新型螺双四氢喹啉。可以在第一阶段在布朗斯台德酸催化剂下选择性地终止反应，以方便地提供相应的官能化的1,2-DHQ。