N-(diphenyl methylene)-2,6-dimethylaniline | 119971-04-9

• 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: N-(diphenyl methylene)-2,6-dimethylaniline
• 英文别名: 2,6-Dimethyl-N-(diphenylmethylene)benzenamine；N-(2,6-dimethylphenyl)-1,1-diphenylmethanimine
• CAS: 119971-04-9
• 化学式: C₂₁H₁₉N
• 分子量: 285.389
• InChiKey: DLUICFZODPVKSP-UHFFFAOYSA-N

物化性质

• 沸点：
  417.7±45.0 °C(Predicted)
• 密度：
  0.99±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  12.4
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2,6-二甲基苯酚 在 tris-(dibenzylideneacetone)dipalladium(0) 4-二甲氨基吡啶 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 N,N-二异丙基乙胺 、 sodium t-butanolate 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 36.0h， 生成 N-(diphenyl methylene)-2,6-dimethylaniline
  参考文献：
  名称：

  钯催化的芳基壬酸酯的胺化。

  摘要：

  报道了钯催化芳基壬二酸酯的胺化的详细研究。配体2-4和6的使用允许富电子的和-中性的芳基壬酸酯与伯胺和仲胺催化胺化。使用Xantphos 5时，各种功能化的芳基壬酸酯的催化胺化反应可产生优异的苯胺收率。甚至2-羧甲基芳基壬酸酯也可以有效地与伯烷基胺偶联。当将卤代芳基壬酸酯与多种胺偶联时，可获得中等产率，其中在大多数情况下，芳基壬酸酯相对于卤代芳基优先反应。总体而言，在钯催化的CN键形成过程中，壬酸芳基酯是三氟甲磺酸酯的有效替代物，因为它们在反应条件下具有更高的稳定性。

  DOI：

  10.1021/jo034962a

文献信息

• Facile Synthesis of Triarylmethanimine Promoted by a Lewis Acid - Base Pair: Theoretical and Experimental Studies
  作者：Yan Liu、Qiwu Yang、Dongling Hao、Wenqin Zhang

  DOI：10.1071/ch12090

  日期：——

  An efficient method for triarylmethanimine synthesis promoted by a Lewis acid–base pair (AlCl3–Et3N) was designed using mechanistic analysis with the aid of density functional theory. A series of triarylmethanimines were successfully prepared under mild conditions in good to excellent yields with a simple work-up procedure. The promoter, the Lewis acid–base pair (AlCl3–Et3N), is inexpensive, efficient, and shows good functional group tolerance. The experimental results show that the electronic effect played a significant role, i.e. the reactions proceeded smoothly when electron-sufficient arylamines and electron-deficient ketones were used as substrates.

  在密度泛函理论的帮助下，利用机理分析设计了一种由路易斯酸碱对（AlCl3-Et3N）促进的三芳基甲亚胺的高效合成方法。通过简单的操作步骤，在温和的条件下成功地制备了一系列三芳基甲亚胺，产率从良好到极佳。路易斯酸碱对（AlCl3-Et3N）是一种廉价、高效且具有良好官能团耐受性的促进剂。实验结果表明，电子效应发挥了重要作用，即当使用电子充足的芳胺和电子不足的酮作为底物时，反应进展顺利。
• Amination Reactions of Aryl Halides with Nitrogen-Containing Reagents Mediated by Palladium/Imidazolium Salt Systems
  作者：Gabriela A. Grasa、Mihai S. Viciu、Jinkun Huang、Steven P. Nolan

  DOI：10.1021/jo010613+

  日期：2001.11.1

  aryl chlorides. The ligand is also effective for the synthesis of benzophenone imines, which can be easily converted to the corresponding primary amines by acid hydrolysis. Less reactive indoles were converted to N-aryl-substituted indoles using as supporting ligand the more donating SIPr.HCl (5, SIPr = 1,3-bis(2,6-diisopropylphenyl)-4,5-dihydroimidazol-2-ylidene). The Pd(OAc)(2)/SIPr.HCl/NaOH system

  亲核N-杂环卡宾已被方便地用作胺改性反应的催化剂改性剂，该反应涉及芳基氯化物，芳基溴化物和芳基碘化物与各种含氮底物。使用各种底物测试了在碱，KO（t）Bu或NaOH存在下使用Pd（0）或Pd（II）源和咪唑鎓盐进行偶联过程的范围。Pd（2）（dba）（3）/IPr.HCl（1，IPr = 1,3-双（2,6-二异丙基苯基）咪唑-2-亚烷基）体系相对于电子中性和富电子的芳基氯化物。该配体对于二苯甲酮亚胺的合成也是有效的，其可以通过酸水解容易地转化为相应的伯胺。使用较多的SIPr.HCl（5，SIPr ＝ 1，3-双（2，6-二异丙基苯基）-4，5-二氢咪唑-2-亚烷基。Pd（OAc）（2）/SIPr.HCl/NaOH系统可有效用于各种吲哚与芳基溴的N-芳基化反应。所开发的通用方案已成功应用于重要的新抗生素合成中的关键中间体的合成。从机理上讲，钯与配体的比例研究强有力地支持了带有一个亲核卡宾配体的活性物质。
• An expedient one-pot synthesis of benzophenone Schiff bases from benzene
  作者：Irena S. Akhrem、Lyudmila V. Afanas’eva、Dzhul’etta V. Avetisyan、Oleg I. Artyushin、Nikolai D. Kagramanov

  DOI：10.1016/j.mencom.2020.03.037

  日期：2020.3

  A simple and efficient one-pot synthesis of benzophenone Schiff bases from benzene, CCl4 and aromatic amines was developed based on the the reaction of benzene with CCl4·AlCl3 complex. This method affords Ph2CCl2 as well as the products of its subsequent reaction with aromatic amines, benzophenone Schiff bases, selectively and in good yields.

  基于苯与CCl4·AlCl3配合物的反应，开发了一种简单，高效的一锅法从苯，CCl4和芳族胺合成二苯甲酮席夫碱。该方法选择性地且高收率地提供了Ph2CCl2及其随后与芳族胺，二苯甲酮席夫碱的反应产物。
• CATALYST COMPONENT FOR PROPYLENE POLYMERIZATION, PREPARATION METHOD THEREFOR AND CATALYST HAVING SAME
  申请人：China Petroleum&Chemical Corporation

  公开号：EP3135699A1

  公开（公告）日：2017-03-01

  The present invention discloses a catalyst component for propene polymerization, comprising titanium, magnesium, halogen, and internal electron donor A, wherein said internal electron donor A is selected from the compouns as shown in Formula I, in Formula I, R is selected from hydrogen, hydroxyl, and substituted or unsubstituted C1-C30 hydrocarbyl, preferably from hydrogen, hydroxyl, and substituted or unsubstituted C1-C20 alkyl, C6-C30 aryl, C6-C30 heteroaryl, C7-C30 alkylaryl and C7-C30 arylalkyl; R1 and R2 may be identical to or different from each other, and are selected from hydrogen and substituted or unsubstituted C1-C30 hydrocarbyl, preferably from hydrogen and substituted or unsubstituted C1-C20 alkyl, C6-C30 aryl, C7-C30 alkylaryl and C7-C30 arylalkyl. According to the present invention, by using the compound as shown in Formula I as internal electron donor compound for propene polymerization, the catalyst has a higher activity, and a slow rate of delay of activity. The obtained polymer has not only a wider molecular weight distribution, but also a high melt index and isotacticity.

  本发明公开了一种用于丙烯聚合的催化剂组分，由钛、镁、卤素和内部电子供体 A 组成，其中所述内部电子供体 A 选自如式 I 所示的化合物、 在式 I 中，R 选自氢、羟基和取代或未取代的 C1-C30 碳氢基，优选选自氢、羟基和取代或未取代的 C1-C20 烷基、C6-C30 芳基、C6-C30 杂芳基、C7-C30 烷芳基和 C7-C30 芳烷基；R1和R2可以彼此相同或不同，并且选自氢和取代或未取代的C1-C30烃基，优选选自氢和取代或未取代的C1-C20烷基、C6-C30芳基、C7-C30烷芳基和C7-C30芳烷基。根据本发明，使用如式 I 所示的化合物作为丙烯聚合的内部电子供体化合物，催化剂具有更高的活性，并且活性延迟的速度较慢。所得到的聚合物不仅分子量分布更广，而且熔融指数和等活度都很高。
• Catalyst component for propene polymerization, preparation method thereof, and catalyst containing the same
  申请人：China Petroleum & Chemical Corporation

  公开号：US10184017B2

  公开（公告）日：2019-01-22

  The present invention discloses a catalyst component for propene polymerization, comprising titanium, magnesium, halogen, and internal electron donor A, wherein said internal electron donor A is selected from the compounds as shown in Formula I, in Formula I, R is selected from hydrogen, hydroxyl, and substituted or unsubstituted C1-C30 hydrocarbyl, preferably from hydrogen, hydroxyl, and substituted or unsubstituted C1-C20 alkyl, C6-C30 aryl, C6-C30 heteroaryl, C7-C30 alkylaryl and C7-C30 arylalkyl; R1 and R2 may be identical to or different from each other, and are selected from hydrogen and substituted or unsubstituted C1-C30 hydrocarbyl, preferably from hydrogen and substituted or unsubstituted C1-C20 alkyl, C6-C30 aryl, C7-C30 alkylaryl and C7-C30 arylalkyl. According to the present invention, by using the compound as shown in Formula I as internal electron donor compound for propene polymerization, the catalyst has a higher activity, and a slow rate of delay of activity. The obtained polymer has not only a wider molecular weight distribution, but also a high melt index and isotacticity.

  本发明公开了一种用于丙烯聚合的催化剂组分，由钛、镁、卤素和内部电子供体 A 组成，其中所述内部电子供体 A 选自如式 I 所示的化合物、 在式 I 中，R 选自氢、羟基和取代或未取代的 C1-C30 碳氢基，优选选自氢、羟基和取代或未取代的 C1-C20 烷基、C6-C30 芳基、C6-C30 杂芳基、C7-C30 烷芳基和 C7-C30 芳烷基；R1和R2可以彼此相同或不同，并且选自氢和取代或未取代的C1-C30烃基，优选选自氢和取代或未取代的C1-C20烷基、C6-C30芳基、C7-C30烷芳基和C7-C30芳烷基。根据本发明，使用如式 I 所示的化合物作为丙烯聚合的内部电子供体化合物，催化剂具有更高的活性，并且活性延迟的速度较慢。所得到的聚合物不仅分子量分布更广，而且熔融指数和等活度都很高。