[N(E)]-N-[(4-bromophenyl)methylene]-α-phenylbenzenemethanamine | 330455-47-5

• 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(E)]-N-[(4-bromophenyl)methylene]-α-phenylbenzenemethanamine
• 英文别名: N-[(1E)-(4-bromophenyl)methylene]-1,1-diphenylmethanamine；(E)-N-(4-bromobenzylidene)-1,1-diphenylmethanamine；(E)-N-(4-bromobenzylidene)diphenylmethanamine
• CAS: 330455-47-5
• 化学式: C₂₀H₁₆BrN
• 分子量: 350.258
• InChiKey: HBUAOQYDJRRCJO-PXLXIMEGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.66
• 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：
  0.05
• 拓扑面积：
  12.36
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  [N(E)]-N-[(4-bromophenyl)methylene]-α-phenylbenzenemethanamine 在 三乙基硅烷 、 正丁基锂 、 三氟甲磺酸 、 硼烷-三甲胺络合物 、 三苯基硼酸酯 、 sodium hexamethyldisilazane 、 sodium carbonate 、 二异丙胺 、 三氟乙酸 、 (R)-2,2'-二苯基-3,3'-(4-联菲酚) 作用下， 以 四氯化碳 、 乙二醇二甲醚 、 乙醚 、 正己烷 、 二氯甲烷 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 69.33h， 生成 (R)-5-(4-bromobenzyl)-3-(3,5-dichlorophenyl)-1,5-dimethylimidazolidine-2,4-dione
  参考文献：
  名称：

  氮丙啶-2-羧酸酯的高度非对映选择性烷基化：LFA-1拮抗剂BIRT-377的对映选择性合成。

  摘要：

  DOI：

  10.1002/anie.200500923
• 作为产物：
  描述：

  对溴苯甲醛 、 二苯甲胺 以 二氯甲烷 为溶剂， 反应 48.0h， 以75%的产率得到[N(E)]-N-[(4-bromophenyl)methylene]-α-phenylbenzenemethanamine
  参考文献：
  名称：

  Si-B键的激活：铜催化的亲核硅与亚胺的加成反应

  摘要：

  通过铜催化的过渡金属化对Si-B键的激活迅速发展为一种生成Cu-Si试剂的实用方法。这些硅亲核试剂干净地添加到醛衍生的亚胺亲电试剂中，从而在质子介质中形成α-甲硅烷基化胺，并且未观察到中间阴离子的碳-氮布鲁克型重排。除了亚胺氮原子上的吸电子基团（例如SO 2 Tol和P（O）Ph 2）外，还可以耐受先前精密的氮取代基，例如苯基或二苯甲基。相同的协议还允许史无前例地添加代表酮的亚胺。

  DOI：

  10.1021/ol200509c

文献信息

• COMPOUNDS AND RELATED METHODS OF USE
  申请人：Jacobsen Eric N.

  公开号：US20130066109A1

  公开（公告）日：2013-03-14

  Described herein are compounds of formula (I), related compositions, and their use, for example in the formation of α-amino acids or a precursor thereof such as an α-aminonitrile.

  本文描述了式（I）的化合物、相关组合物及其用途，例如在形成α-氨基酸或其前体（如α-氨基腈）中的应用。
• Aziridinyl Vinyl Ketones from the Asymmetric Catalytic Aziridination Reaction
  作者：Yonghong Deng、Young Rok Lee、Cory A. Newman、William D. Wulff

  DOI：10.1002/ejoc.200601126

  日期：2007.5

  Under the aegis of boron Lewis acids, prepared from either the vanol or vapol ligand, vinyl aziridinyl ketones can be obtained with a high degree of asymmetric induction from the catalytic asymmetric aziridination reaction (AZ) of imines and vinyl diazomethyl ketones. The products have potential as synthons for five-carbon chiral amines. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany

  在由 vanol 或 vapol 配体制备的硼路易斯酸的支持下，可以通过亚胺和乙烯基重氮甲基酮的催化不对称氮丙啶化反应 (AZ) 的高度不对称诱导获得乙烯基氮丙啶酮。该产品具有作为五碳手性胺合成子的潜力。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)
• Synthesis of 1,2-Dihydropyridines Using Vinyloxiranes as Masked Dienolates in Imino-Aldol Reactions
  作者：Bernhard Brunner、Nicole Stogaitis、Mark Lautens

  DOI：10.1021/ol061086p

  日期：2006.8.1

  application of vinyloxiranes, substituted with an electron-withdrawing group, as masked dienolates in vinylogous imino-aldol reactions was achieved. Under the reaction conditions highly substituted 1,2-dihydropyridines were obtained in moderate to good yields. Mechanistic studies indicate that the reaction proceeds via the formation of an (E)-amino-alpha,beta-unsaturated aldehyde, followed by isomerization

  [反应：见正文]已实现了用吸电子基团取代的乙烯基环氧乙烷作为掩蔽的二烯酸酯在乙烯基亚氨基羟醛反应中的应用。在反应条件下，以中等至良好的产率获得了高度取代的1,2-二氢吡啶。机理研究表明，该反应通过形成（E）-氨基-α，β-不饱和醛，然后异构化为（Z）-异构体，环化并消除水分子而进行，从而导致生成1,2-二氢吡啶。
• Regulation of Orthogonal Functions in a Dual Catalyst System. Subservient Role of a Nonchiral Lewis Acid in an Asymmetric Catalytic Heteroatom Diels−Alder Reaction
  作者：Cory A. Newman、Jon C. Antilla、Pei Chen、Alexander V. Predeus、Lee Fielding、William D. Wulff

  DOI：10.1021/ja069019d

  日期：2007.6.13

  A catalytic asymmetric heteroatom Diels-Alder reaction of unactivated imines with Danishefsky's diene is described which gives high asymmetric induction for N-benzhydryl imines derived from a variety of aldehydes. The catalyst is derived from B(OPh)(3) and the VAPOL ligand and gives good induction, but the reaction stalls and does not give high conversion (similar to 50%). It was found that in the presence of both the chiral catalyst and excess amounts of B(OPh)(3) the reaction proceeds to completion and gives high yields of the dihydropiperidinone product. Despite the presence of large quantities of the nonchiral Lewis acid B(OPh)(3), the asymmetric induction of the product remains constant (90% ee) as the amount of B(OPh)(3) is steadily increased and does not drop off until the ratio of B(OPh)(3) to VAPOL is 100:1 (82% ee). These observations are interpreted as involving highly separated and different activities for the chiral and nonchiral Lewis acids present in the reaction. Specifically, the excess B(OPh)(3) serves to bind to the product and release the chiral catalyst to turnover more starting material. The B(OPh)(3) does not compete in turning over the starting material, and a series of binding studies reveal that this is likely due to a combination of two factors. The binding studies reveal that the chiral catalyst binds to the starting imine 7 times more strongly than does B(OPh)(3). However, in order to explain the constant asymmetric induction observed despite the addition of increasing amounts of B(OPh)(3), the rate of the reaction of the imine complexed with the chiral catalyst must be at least 10 times faster than the reaction of the imine complexed with B(OPh)(3). Finally, a catalyst generated from BINOL and B(OPh)(3) does not show this phenomenon.
• Catalytic Asymmetric Aziridination with a Chiral VAPOL−Boron Lewis Acid
  作者：Jon C. Antilla、William D. Wulff

  DOI：10.1021/ja9905187

  日期：1999.6.1