(R)-3,3'-dibromo-1,1'-binaphthyl-2,2'-diamine

• 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: (R)-3,3'-dibromo-1,1'-binaphthyl-2,2'-diamine
• 英文别名: 1-(2-Amino-3-bromonaphthalen-1-yl)-3-bromonaphthalen-2-amine
• 化学式: C₂₀H₁₄Br₂N₂
• 分子量: 442.153
• InChiKey: LLZFYNZVDXHEST-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  52
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-3,3'-dibromo-1,1'-binaphthyl-2,2'-diamine 在 次氯酸叔丁酯 作用下， 以 叔丁醇 为溶剂， 反应 19.0h， 以77%的产率得到6,9-dibromo-7,8-diaza[5]helicene
  参考文献：
  名称：

  A facile synthesis of functionalized 7,8-diaza[5]helicenes through an oxidative ring-closure of 1,1’-binaphthalene-2,2’-diamines (BINAMs)

  摘要：

  已开发出一种简便且中等官能团容忍性的合成方法，用于制备7,8-二氮杂[5]螺芳烃。该方法包括在存在碱（2,6-吡啶）的条件下，将1,1'-二萘基-2,2'-二胺（BINAM）衍生物与含氯氧化剂（t-BuOCl）进行氧化环闭合反应。此外，还研究了新合成化合物的基本理化性质。

  DOI：

  10.3762/bjoc.11.2
• 作为产物：
  描述：

  (R)-3,3'-dibromo-5,6,7,8,5',6',7',8'-octahydro-[1,1']-binaphthalenyl-2,2'-diamine 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 苯 为溶剂， 反应 0.08h， 以74%的产率得到(R)-3,3'-dibromo-1,1'-binaphthyl-2,2'-diamine
  参考文献：
  名称：

  Facile Synthesis of Structurally Diverse 3,3′-Disubstituted 1,1′-Binaphthyl-2,2′-diamines in Optically Pure Forms

  摘要：

  A new synthetic route to 3,3'-dihalo BINAMs based on the direct halogenation of H-8-BINAM and Subsequent rearomatization to the binaphthyl core has been developed. The combination of this new procedure and Pd-catalyzed Coupling reactions enabled us to synthesize various 3,3'-disubstituted BINAMs in only three steps starting from H-8-BINAM.

  DOI：

  10.1021/jo8011368

文献信息

• Oxidative skeletal rearrangement of 1,1′-binaphthalene-2,2′-diamines (BINAMs) <i>via</i> C–C bond cleavage and nitrogen migration: a versatile synthesis of U-shaped azaacenes
  作者：Youhei Takeda、Masato Okazaki、Satoshi Minakata

  DOI：10.1039/c4cc04911j

  日期：——

  An oxidative skeletal rearrangement of 1,1′-binaphthalene-2,2′-diamines (BINAMs) that involves the cleavage of a strong C–C single bond of the binaphthalene unit and the nitrogen migration has been discovered.

  一种涉及1,1'-联萘-2,2'-二胺（BINAMs）的氧化骨架重排反应已被发现，其中涉及联萘单元中强C-C单键的断裂和氮迁移。
• Synergistic Catalysis of Ionic Brønsted Acid and Photosensitizer for a Redox Neutral Asymmetric α-Coupling of <i>N</i>-Arylaminomethanes with Aldimines
  作者：Daisuke Uraguchi、Natsuko Kinoshita、Tomohito Kizu、Takashi Ooi

  DOI：10.1021/jacs.5b09329

  日期：2015.11.4

  A redox neutral, highly enantioselective coupling between N-arylaminomethanes and N-sulfonyl aldimines was developed by harnessing the efficient catalysis of P-spiro chiral arylaminophosphonium barfate and a transition-metal photosensitizer under visible light irradiation. This mode of synergistic catalysis provides a powerful strategy for controlling the bond-forming processes of reactive radical intermediates.
• A facile synthesis of functionalized 7,8-diaza[5]helicenes through an oxidative ring-closure of 1,1’-binaphthalene-2,2’-diamines (BINAMs)
  作者：Youhei Takeda、Masato Okazaki、Yoshiaki Maruoka、Satoshi Minakata

  DOI：10.3762/bjoc.11.2

  日期：——

  A facile and moderately functional-group-tolerant synthetic method for the preparation of 7,8-diaza[5]helicenes has been developed. It comprises of an oxidative ring-closing process of 1,1’-binaphthalene-2,2’-diamine (BINAM) derivatives with a chlorine-containing oxidant (t-BuOCl) in the presence of a base (2,6-lutidine). In addition the basic physicochemical properties of newly synthesized compounds have been investigated.

  已开发出一种简便且中等官能团容忍性的合成方法，用于制备7,8-二氮杂[5]螺芳烃。该方法包括在存在碱（2,6-吡啶）的条件下，将1,1'-二萘基-2,2'-二胺（BINAM）衍生物与含氯氧化剂（t-BuOCl）进行氧化环闭合反应。此外，还研究了新合成化合物的基本理化性质。
• Facile Synthesis of Structurally Diverse 3,3′-Disubstituted 1,1′-Binaphthyl-2,2′-diamines in Optically Pure Forms
  作者：Taichi Kano、Youhei Tanaka、Kenta Osawa、Taiga Yurino、Keiji Maruoka

  DOI：10.1021/jo8011368

  日期：2008.9.19

  A new synthetic route to 3,3'-dihalo BINAMs based on the direct halogenation of H-8-BINAM and Subsequent rearomatization to the binaphthyl core has been developed. The combination of this new procedure and Pd-catalyzed Coupling reactions enabled us to synthesize various 3,3'-disubstituted BINAMs in only three steps starting from H-8-BINAM.