(S,S)-N¹-(3',5'-diethylbiphenyl-2-yl)-1,2-diphenylethane-1,2-diamine | 1513846-44-0

• 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'-diethylbiphenyl-2-yl)-1,2-diphenylethane-1,2-diamine
• 英文别名: (1S,2S)-N'-[2-(3,5-diethylphenyl)phenyl]-1,2-diphenylethane-1,2-diamine
• CAS: 1513846-44-0
• 化学式: C₃₀H₃₂N₂
• 分子量: 420.597
• InChiKey: BQHJGCGNRXWYLP-KYJUHHDHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 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'-diethylbiphenyl-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 19.0h， 生成 (S,S)-1-(3',5'-diethylbiphenyl-2-yl)-3-mesityl-4,5-diphenyl-4,5-dihydro-1H-imidazol-3-iumtetrafluoroborate
  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
• 作为产物：
  描述：

  1,2-二溴苯 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'-diethylbiphenyl-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
• 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。
• 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。
• [EN] BORON NITROGEN LIGAND BASED ON CHIRAL 1,2-ETHYLENEDIAMINE BACKBONE AND PREPARATION METHOD AND USE THEREOF<br/>[FR] LIGAND DE BORE AZOTE BASÉ SUR UN SQUELETTE DE 1,2-ÉTHYLÈNEDIAMINE CHIRAL, SON PROCÉDÉ DE PRÉPARATION ET SON UTILISATION<br/>[ZH] 手性1,2-乙二胺骨架的硼氮配体及其制备方法与应用
  申请人：SUZHOU RES INSTITUTE LANZHOU INSTITUTE OF CHEMICAL PHYSICS CHINESE ACADEMY OF SCIENCES

  公开号：WO2020019911A1

  公开（公告）日：2020-01-30

  公开了一种手性1,2-乙二胺骨架的硼氮配体及其制备方法与应用。所述硼氮配体的结构式如式(I)所示，其中，R1、R2、R3分别至少独立地选自取代或未取代的C3～C10的环烷基、C1～C10的烷基或芳基；R4、R5、R6、R7、R8、R9、R10、R11、R12分别至少独立地选自氢、卤素、取代或未取代的C1～C10的烷基、C1～C4的烷氧基、C3～C30的环烷基或芳基；Ar1和Ar2分别至少独立地选自取代或未取代的C6～C30的芳基。制备方法简单，可以制成消旋或手性的硼氮配体，该配体可用作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。