(1R)-(1,3-diphenylallyl)-(4-methoxyphenyl)amine | 1062573-84-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (1R)-(1,3-diphenylallyl)-(4-methoxyphenyl)amine
• 英文别名: (R,E)-N-(1,3-diphenylallyl)-4-methoxyaniline；(E)-N-(1,3-diphenylallyl)-4-methoxyaniline；N-[(E,1R)-1,3-diphenylprop-2-enyl]-4-methoxyaniline
• CAS: 1062573-84-5
• 化学式: C₂₂H₂₁NO
• 分子量: 315.415
• InChiKey: NCQJDPPVLLYZNO-YAECTWJJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  21.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1R)-(1,3-diphenylallyl)-(4-methoxyphenyl)amine 、 溴甲苯 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 以95%的产率得到(1R)-benzyl-(1,3-diphenylallyl)-(4-methoxyphenyl)amine
  参考文献：
  名称：

  Pd-catalyzed asymmetric allylic aminations with aromatic amine nucleophiles using chiral diaminophosphine oxides: DIAPHOXs

  摘要：

  Asymmetric allylic aminations with aromatic amine nucleophiles using Pd-DIAPHOX catalyst systems are described. The asymmetric allylic aminations of various allylic carbonates proceeded using 2-5 mol % of the catalyst and BSA, providing the corresponding N-aryl chiral allylic amines in up to 99% ee for cyclic substrates, and in up to 97% ee for acyclic substrates. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.07.015
• 作为产物：
  描述：

  甲氧苯胺 、 ethyl (E)-1,3-diphenyl-2-propen-1-yl carbonate 在 bis(η3-allyl-μ-chloropalladium(II)) 三乙烯二胺 、 N,O-双三甲硅基乙酰胺 作用下， 以 乙醚 为溶剂， 反应 24.17h， 以99%的产率得到(1R)-(1,3-diphenylallyl)-(4-methoxyphenyl)amine
  参考文献：
  名称：

  Pd-catalyzed asymmetric allylic aminations with aromatic amine nucleophiles using chiral diaminophosphine oxides: DIAPHOXs

  摘要：

  Asymmetric allylic aminations with aromatic amine nucleophiles using Pd-DIAPHOX catalyst systems are described. The asymmetric allylic aminations of various allylic carbonates proceeded using 2-5 mol % of the catalyst and BSA, providing the corresponding N-aryl chiral allylic amines in up to 99% ee for cyclic substrates, and in up to 97% ee for acyclic substrates. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.07.015

文献信息

• A <scp>d</scp> -Camphor-Based Schiff Base as a Highly Efficient N,P Ligand for Enantioselective Palladium-Catalyzed Allylic Substitutions
  作者：Qiao-Ling Liu、Weifeng Chen、Qun-Ying Jiang、Xing-Feng Bai、Zhifang Li、Zheng Xu、Li-Wen Xu

  DOI：10.1002/cctc.201600084

  日期：2016.4.20

  New Schiff bases derived from chiral d‐camphor were determined to be effective phosphine ligands for the asymmetric palladium‐catalyzed allylic alkylation of activated methylene compounds, the allylic etherification of alcohols, and the allylic amination of primary amines or secondary amines, in which the corresponding products with various functional groups were achieved in good yields with excellent

  从手性衍生的新的席夫碱d -樟脑被确定为用于活化的亚甲基化合物的不对称钯催化的烯丙基烷基化，醇的烯丙基醚化，和伯胺或仲胺的烯丙基胺化，其中，对应的有效的膦配体具有良好收率和优异的对映选择性（高达> 99％ee），可以得到具有各种官能团的产物 。值得注意的是，衍生自席夫碱L2的钯催化剂提供了迄今为止报道的最高水平的对映选择性，可用于烯丙基取代反应，包括烯丙基醚化和烯丙基胺化反应，从而揭示了d的特殊作用。钯催化的烯丙基取代反应中源自樟脑的席夫碱。
• A new type of ferrocene-based phosphine-tert-butylsulfinamide ligand: synthesis and application in asymmetric catalysis
  作者：Jiangwei Ma、Chuang Li、Dongxu Zhang、Yang Lei、Muqiong Li、Ru Jiang、Weiping Chen

  DOI：10.1039/c5ra03010b

  日期：——

  The first example of P,S-bidentate ligands containing both a planar chiral scaffold and a chiral sulfinamide moiety were reported.

  包含平面手性支架和手性亚砜基团的P、S-双齿配体的第一个示例已经报道。
• New spiro phosphinooxazolines for palladium-catalyzed asymmetric allylic amination
  作者：Yanfeng Gao、Zhongxuan Qiu、Rui Sun、Nanxing Gao、Guorui Cao、Dawei Teng

  DOI：10.1016/j.tetlet.2018.09.044

  日期：2018.10

  The new conformational rigid spiro phosphinooxazolines 1 were synthesized from 7-bromo-1-indanone. The asymmetric catalytic potential of them was demonstrated in the asymmetric palladium catalyzed allylic amination. High yields and enantioselectivities were obtained with alkylamines.

  新的构象刚性螺phosphinooxazolines 1从7-溴-1-二氢茚酮的合成。它们的不对称催化潜力在不对称钯催化的烯丙基胺化反应中得到证明。用烷基胺获得高产率和对映选择性。
• New P,N_sp3ligands for palladium-catalyzed asymmetric allylic substitutions
  作者：Qin Su、Chuan-Jin Hou、De-Quan Wei、Hao Qin、Ding-Hua Liang、Xiang-Ping Hu

  DOI：10.1039/d3ob00519d

  日期：——

  New P,Nsp3 bidentate ligands containing two chiral carbon centers were developed and applied to palladium-catalyzed asymmetric allylic substitution reactions. Good generalities with various nucleophiles, including carbon, nitrogen and oxygen containing nucleophiles, were achieved with up to 96% ee and 98% yield. This reaction provides an efficient method for the asymmetric formation of C–C, C–N and

  开发了包含两个手性碳中心的新型 P,N sp3双齿配体，并将其应用于钯催化的不对称烯丙基取代反应。与各种亲核试剂（包括含碳、含氮和含氧的亲核试剂）的良好通用性达到了高达 96% 的 ee 和 98% 的产率。该反应为C-C、C-N和C-O键的不对称形成提供了一种有效的方法。