(S,S)-N¹-(3',5'-dimethylbiphenyl-2-yl)-1,2-diphenylethane-1,2-diamine | 1513846-43-9

• 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: (S,S)-N¹-(3',5'-dimethylbiphenyl-2-yl)-1,2-diphenylethane-1,2-diamine
• 英文别名: (1S,2S)-N'-[2-(3,5-dimethylphenyl)phenyl]-1,2-diphenylethane-1,2-diamine
• CAS: 1513846-43-9
• 化学式: C₂₈H₂₈N₂
• 分子量: 392.544
• InChiKey: NUYYRTPGZYYGTD-NSOVKSMOSA-N

物化性质

• 沸点：
  566.3±50.0 °C(Predicted)
• 密度：
  1.122±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  38
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S,S)-N¹-(3',5'-dimethylbiphenyl-2-yl)-1,2-diphenylethane-1,2-diamine 在 palladium diacetate 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 sodium t-butanolate 作用下， 以 甲苯 为溶剂， 反应 15.0h， 生成 (4S,5S)-1-(3',5'-dimethyl-[1,1'-biphenyl]-2-yl)-3-mesityl-4,5-diphenyl-4,5-dihydro-1H-imidazol-3-ium tetrafluoroborate
  参考文献：
  名称：

  一种新的手性C1对称NHC催化的除α-芳基取代的α，β-二取代的enals：全功能化的二氢吡喃酮的对映选择性合成。

  摘要：

  通过高活性酰基偶氮中间体成功开发了第一个对映选择性NHC催化的α-芳基取代的α，β-二取代不饱和醛的活化方法。新的C1对称联芳基饱和的咪唑鎓盐具有出色的能力，能够实现以前无法进行的转化，并且可以以高收率和出色的对映选择性有效地合成相应的完全官能化的二氢吡喃酮。

  DOI：

  10.1039/c5cc00118h
• 作为产物：
  描述：

  3,5-二甲基苯硼酸 在 四(三苯基膦)钯 、 potassium tert-butylate 、 palladium diacetate 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 sodium t-butanolate 作用下， 以 乙醇 、 水 、 甲苯 为溶剂， 反应 18.5h， 生成 (S,S)-N¹-(3',5'-dimethylbiphenyl-2-yl)-1,2-diphenylethane-1,2-diamine
  参考文献：
  名称：

  Asymmetric Homoenolate Additions to Acyl Phosphonates through Rational Design of a Tailored N-Heterocyclic Carbene Catalyst

  摘要：

  A highly selective NHC-catalyzed synthesis of gamma-butyrolactones from the fusion of enals and alpha-ketophosphonates has been developed. Computational modeling of competing transition states guided a rational design strategy to achieve enhanced levels of enantioselectivity with a new tailored C-1-symmetric biaryl-saturated imidazolium-derived NHC catalyst.

  DOI：

  10.1021/ja410932t

文献信息

• Chiral Bidentate Boryl Ligand Enabled Iridium-Catalyzed Asymmetric C(sp²)–H Borylation of Diarylmethylamines
  作者：Xiaoliang Zou、Haonan Zhao、Yinwu Li、Qian Gao、Zhuofeng Ke、Senmiao Xu

  DOI：10.1021/jacs.8b13756

  日期：2019.4.3

  straightforwardly in three steps starting from readily available ( S, S)-1,2-diphenyl-1,2-ethanediamie (( S, S)-DPEN). The Ir-catalyzed C(sp2)-H borylation comprises two parts. The first part is desymmetrization of prochiral diarylmethylamines. In the presence of L3/Ir, a vast array of corresponding borylated products were obtained with high regioselectivity and good to excellent enantioselectivities (26 examples

  旋光有机硼酸及其衍生物是有机化学、催化和药物化学中重要的目标化合物家族。然而，通过原子和步骤经济的方式合成这些化合物的不对称催化例子很少见。在此，我们报告了由游离胺基团引导的芳香族 CH 键的螯合物导向的铱催化不对称 C(sp2)-H 硼酸化。这些转化的成功依赖于手性双齿硼酸配体 (L) 的新家族。它们可以从容易获得的 (S, S)-1,2-二苯基-1,2-乙二胺 ((S, S)-DPEN) 开始，分三步直接合成。Ir 催化的 C(sp2)-H 硼酸化包括两部分。第一部分是前手性二芳基甲基胺的去对称化。在 L3/Ir 存在下，获得了大量相应的硼化产物，具有高区域选择性和良好的对映选择性（26 个实例，高达 96% ee）。第二部分，外消旋二芳基甲胺的动力学拆分，也进行了。使用 L8 时获得了良好的选择性值（高达 68%，11 个实例）。我们还展示了当前方法对几种转化的克级反应的综合效用。硼化产物的
• A Cooperative N-Heterocyclic Carbene/Chiral Phosphate Catalysis System for Allenolate Annulations
  作者：Anna Lee、Karl A. Scheidt

  DOI：10.1002/anie.201403446

  日期：2014.7.14

  The highly enantioselective NHC‐catalyzed [3+2] annulation reaction with α,β‐alkynals and α‐ketoesters has been developed. A new mode of cooperative catalysis involving the combination of a chiral Brønsted acid and a C1‐symmetric biaryl saturated‐imidazolium precatalyst was required to generate the desired γ‐crotonolactones in high yields and levels of enantioselectivity.

  已开发出高对映选择性 NHC 催化的 [3+2] 与 α,β-炔醛和 α-酮酯的环化反应。需要一种新的协同催化模式，包括手性布朗斯台德酸和 C 1对称联芳基饱和咪唑鎓预催化剂的组合，以高产率和对映选择性水平生成所需的 γ-巴豆内酯。
• BORON-NITROGEN LIGAND WITH CHIRAL 1,2-ETHYLENEDIAMINE BACKBONE, AND PREPARATION METHOD AND USE THEREOF
  申请人：SUZHOU RESEARCH INSTITUTE, LANZHOU INSTITUTE OF CHEMICAL PHYSICS, CHINESE ACADEMY OF SCIENCES

  公开号：US20210253606A1

  公开（公告）日：2021-08-19

  A boron-nitrogen ligand with a chiral 1,2-ethylenediamine backbone, a preparing method and used thereof are provided. The structural formula of the boron-nitrogen ligand is as shown in formula (I): wherein R 1 , R 2 and R 3 are respectively at least independently selected from substituted or unsubstituted C 3 -C 10 cycloalkyl, C 1 -C 10 alkyl or aryl; R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 and R 12 are respectively at least independently selected from hydrogen, halogen, substituted or unsubstituted C 1 -C 10 alkyl, C 1 -C 4 alkoxy, C 3 -C 30 cycloalkyl or aryl; Ar 1 and Ar 2 are respectively at least independently selected from substituted or unsubstituted C 6 -C 30 aryl. The preparation method of the present application is simple, and can be used for preparing a racemic or chiral boron-nitrogen ligand, which can be used as a catalyst for an asymmetric catalytic reaction and has economic practicability and industrial application prospects.

  提供了一种具有手性1,2-乙二胺骨架的硼-氮配体，提供了一种制备方法和用途。硼-氮配体的结构式如下所示：其中R1、R2和R3分别至少独立地选自取代或未取代的C3-C10环烷基、C1-C10烷基或芳基；R4、R5、R6、R7、R8、R9、R10、R11和R12分别至少独立地选自氢、卤素、取代或未取代的C1-C10烷基、C1-C4烷氧基、C3-C30环烷基或芳基；Ar1和Ar2分别至少独立地选自取代或未取代的C6-C30芳基。本申请的制备方法简单，可用于制备光学活性或手性硼-氮配体，可用作不对称催化反应的催化剂，并具有经济实用性和工业应用前景。
• Simple Ether‐Directed Enantioselective C( <i>sp</i> ³ )−H Borylation of Cyclopropanes Enabled by Iridium Catalysis
  作者：Tian Xie、Lili Chen、Zhenlu Shen、Senmiao Xu

  DOI：10.1002/anie.202300199

  日期：2023.3.27

  Simple ether-directed enantioselective C(sp3)−H borylation of cyclopropanes was accomplished by CBL/iridium catalysis for the first time. The reported method features tolerance of a broad range of functional groups (38 examples), excellent enantioselectivity (up to 99 % ee), and high turnover numbers (up to 335).

  首次通过CBL /iridium 催化实现了环丙烷的简单醚导向对映选择性 C( sp 3 )−H 硼酸化。报告的方法具有广泛的官能团耐受性（38 个示例）、出色的对映选择性（高达 99% ee）和高转换数（高达 335）。
• Boron-nitrogen ligand with chiral 1,2-ethylenediamine backbone, and preparation method and use thereof
  申请人：Lanzhou Institute of Chemical Physics, Chinese Academy of Science

  公开号：US11161861B2

  公开（公告）日：2021-11-02

  A boron-nitrogen ligand with a chiral 1,2-ethylenediamine backbone, a preparing method and used thereof are provided. The structural formula of the boron-nitrogen ligand is as shown in formula (I): wherein R1, R2 and R3 are respectively at least independently selected from substituted or unsubstituted C3-C10 cycloalkyl, C1-C10 alkyl or aryl; R4, R5, R6, R7, R8, R9, R10, R11 and R12 are respectively at least independently selected from hydrogen, halogen, substituted or unsubstituted C1-C10 alkyl, C1-C4 alkoxy, C3-C30 cycloalkyl or aryl; Ar1 and Ar2 are respectively at least independently selected from substituted or unsubstituted C6-C30 aryl. The preparation method of the present application is simple, and can be used for preparing a racemic or chiral boron-nitrogen ligand, which can be used as a catalyst for an asymmetric catalytic reaction and has economic practicability and industrial application prospects.

  本发明提供了一种具有手性 1,2-乙二胺骨架的硼氮配体及其制备方法和用途。硼氮配体的结构式如式（I）所示： 其中，R1、R2和R3分别至少独立选自取代或未取代的C3-C10环烷基、C1-C10烷基或芳基；R4、R5、R6、R7、R8、R9、R10、R11和R12分别至少独立选自氢、卤素、取代或未取代的C1-C10烷基、C1-C4烷氧基、C3-C30环烷基或芳基；Ar1和Ar2分别至少独立选自取代或未取代的C6-C30芳基。本申请的制备方法简单，可用于制备外消旋或手性硼氮配体，可作为不对称催化反应的催化剂，具有经济实用性和工业应用前景。