benzil monoanil | 1081814-25-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: benzil monoanil
• 英文别名: (Z)-1,2-diphenyl-2-(phenylimino)ethan-1-one；2,3,4-triphenyl-1-oxa-4-azabutadiene；benzile-monoanile
• CAS: 1081814-25-6
• 化学式: C₂₀H₁₅NO
• 分子量: 285.345
• InChiKey: WTZNNBFUSZQZEX-VZCXRCSSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.69
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  29.43
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  benzil monoanil 在 Ru clay 氢气 作用下， 以 苯 为溶剂， 100.0 ℃ 、6.21 MPa 条件下， 反应 44.0h， 以95%的产率得到1,2-diphenyl-2-(phenylamino)ethanone
  参考文献：
  名称：

  Ruthenium clay catalyzed reduction of α-iminoesters and α-iminoketones, and the reductive amination of α-ketoesters

  摘要：

  The reduction of alpha-iminoesters and alpha-iminoketones to the corresponding amino compounds was accomplished using ruthenium clay as the catalyst, at 75-100 degrees C and 600-900 psi H-2. The same catalyst proved efficient for the reductive amination of alpha-ketoesters (100 degrees C, 600 psi H-2). Diastereomeric excesses of up to 78% were obtained in the reductive amination reaction. (C) 2000 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0022-328x(99)00614-2
• 作为产物：
  描述：

  1,2-diphenyl-2-(phenylamino)ethanone 在 氧气 作用下， 以 various solvent(s) 为溶剂， 反应 6.0h， 生成 benzil monoanil
  参考文献：
  名称：

  Structure and conformation of 2,3,4-triphenyl-1-oxa-4-azabutadiene

  摘要：

  2,3,4-triphenyl-1-oxa-4-azabutadine (C20H15NO) has been studied by X-ray analysis and AMI molecular orbital methods. It crystallises in the triclinic space group P-l with a = 9.414(3), b = 10.479(3), c = 8.385(2) Angstrom, alpha = 103.31(3)degrees beta = 97.10(3)degrees, gamma = 74.09(1)degrees, V = 772.5(4) Angstrom(3), Z = 2, D-c = 1.227 g cm(-3), and mu(MoK alpha) = 0.075 mm(-1) and F-000 = 300. The structure was solved by direct methods and refined to R = 0.043 for 2672 reflections [I > 2 sigma(1)]. The conformational analysis of the title compound were investigated by semi-empirical quantum mechanical AM1 calculations. The minimum conformation energies were calculated as a function of the three torsion angles theta(1)(O(1)C(7)C(8)N( 1)), theta(2)(C(8)N(1)C(IS)C(16)) and theta(3)(C(14)C(9)C(8)N(1)). The results are compared with the X-ray results. C=O and C=N groups are twisted about each other by 95.5(2)degrees. (C) 2000 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0022-2860(00)00521-4

文献信息

• Preparation and Application of α-Imino Ketones through One-Pot Tandem Reactions Based on Heyns Rearrangement
  作者：Ling Li、Shiqi Zhang、Xiongfei Deng、Guangxun Li、Zhuo Tang、Gang Zhao

  DOI：10.1021/acs.orglett.1c02390

  日期：2021.9.3

  α-Imino ketone is a useful building block for the preparation of α-amino ketones and α-amino alcohols. However, its preparation has been seldomly seen. Herein, a metal-free and operationally simple strategy has been developed to generate α-imino ketones with high regioselectivity. Meanwhile, the method allowed for the preparation of various N,O-ketals with high regioselectivities and diastereoselectivities

  α-亚氨基酮是制备 α-氨基酮和 α-氨基醇的有用构件。然而，很少有人看到它的准备工作。在此，已开发出一种无金属且操作简单的策略来生成具有高区域选择性的 α-亚氨基酮。同时，该方法允许通过一锅级联反应制备具有高区域选择性和非对映选择性的各种N,O-缩酮。
• From benzil arylimines to 2H-benzo-1,4-thiazines, benzothiazoles or indoles
  作者：Jean-Damien Charrier、Cyrille Landreau、David Deniaud、Françoise Reliquet、Alain Reliquet、Jean Claude Meslin

  DOI：10.1016/s0040-4020(01)00317-9

  日期：2001.5

  A series of benzil monoarylimines (1) was treated with phosphorus pentasulfide in refluxing toluene or xylene. Thionation of 1 occurred readily to afford either 2H-benzo-1,4-thiazines (2) or indoles (4) via annulation reactions, depending strongly on the nature of the meta substituent of the arylamino group. Mechanisms for these rearrangements were proposed. Furthermore, subsequent oxidation of 2 provided

  在回流的甲苯或二甲苯中，用五硫化二磷处理了一系列的苄基单芳烃（1）。发生1的亚硫酰化很容易通过环化反应提供2个H-苯并-1,4-噻嗪（2）或吲哚（4），这在很大程度上取决于芳基氨基间位取代基的性质。提出了用于这些重排的机制。此外，随后氧化2得到苯并噻唑（3）。所有化合物均通过IR，MS，13 C和1 H NMR进行了全面表征。
• Cariou, Michel; Carlier, Roger; Simonet, Jacques, Bulletin de la Societe Chimique de France, 1986, # 5, p. 781 - 792
  作者：Cariou, Michel、Carlier, Roger、Simonet, Jacques

  DOI：——

  日期：——
• C_sp3–H Imination Using Arylazo Sulfone as a N Source: An Approach to Access Imines
  作者：Yulei Zhao、Shuai Li、Yuhang Fan、Jun Cao、Xiaotong Dong、Ruiqing Wang、Laijin Tian

  DOI：10.1021/acs.orglett.3c02283

  日期：2023.8.11