5,5'-dibromo-1'H,3H-[2,3'-biindol]-3-one | 92797-11-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 5,5'-dibromo-1'H,3H-[2,3'-biindol]-3-one
• 英文别名: 5,5'-dibromo-1'H-[2,3']biindolyl-3-one；5-Brom-2-<5-brom-indol-3-yl>-3H-pseudoindol-3-on；5-bromo-2-(5-bromo-1H-indol-3-yl)indol-3-one
• CAS: 92797-11-0
• 化学式: C₁₆H₈Br₂N₂O
• 分子量: 404.06
• InChiKey: GJUIVHFZEJPUMO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  21
• 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：
  45.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,2-difluoro-1-phenyl-1-trimethylsiloxyethene 、 5,5'-dibromo-1'H,3H-[2,3'-biindol]-3-one 在 (S)-3,3'-bis(2,4,6-tri-iso-propylphenyl)-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate 作用下， 以 四氢呋喃 为溶剂， 以73%的产率得到(R)-5-bromo-2-(5-bromo-1H-indol-3-yl)-2-(1,1-difluoro-2-oxo-2-phenylethyl)indolin-3-one
  参考文献：
  名称：

  Catalytic Asymmetric Mukaiyama–Mannich Reaction of Cyclic C-Acylimines with Difluoroenoxysilanes: Access to Difluoroalkylated Indolin-3-ones

  摘要：

  A catalytic enantioselective Mukaiyama-Mannich reaction of cyclic C-acylimines with difluoroenoxysilanes is reported.(S)-TRIP enables the enantioselective synthesis of a series of novel difluoroalkylated indolin-3-ones bearing a quaternary stereocenter in up to 97% yield and 98% ee. The synthetic utility of this protocol is highlighted by efficient conversion of the products to the corresponding indolin-3-one derivatives without any erosion of the enantiopurity.

  DOI：

  10.1021/acs.orglett.7b03213
• 作为产物：
  描述：

  5-溴吲哚 在 2,2,6,6-四甲基哌啶氧化物 、 sodium acetate 、 silver carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以75%的产率得到5,5'-dibromo-1'H,3H-[2,3'-biindol]-3-one
  参考文献：
  名称：

  TEMPO催化的通过吲哚3酮中间体形成3,2'-联吲哚2酮的氧化均偶联途径†

  摘要：

  成功地证明了在非定向基团条件下借助TEMPO催化和银氧化剂对游离吲哚衍生物进行的C2选择性芳基化和C3选择性羰基化。这种新方法既原子又高效，并且适用于广泛的底物，从而可以中等至极高的产率合成一系列具有合成价值的3,2'-联吲哚-2-酮。

  DOI：

  10.1039/c6ra24834a

文献信息

• Chiral phosphoric acid-catalyzed direct asymmetric mannich reaction of cyclic<i>C</i>-acylimines with simple ketones: facile access to C2-quaternary indolin-3-ones
  作者：Jin-Shan Li、Yong-Jie Liu、Shen Li、Jun-An Ma

  DOI：10.1039/c8cc05125a

  日期：——

  A chiral Brønsted acid-catalyzed direct asymmetric Mannich reaction of simple ketones with cyclic C-acylimines has been established for the synthesis of C2-quaternary indolin-3-ones. In the presence of 5–10 mol% chiral phosphoric acid, a series of 2-(2-oxo-2-phenylethyl)-2-arylindolin-3-ones were obtained in good to high yield with up to 99% ee. The adducts obtained could be readily converted into

  建立了手性布朗斯台德酸催化的简单酮类与环状C-酰基亚胺的直接不对称曼尼希反应，用于合成C2-季吲哚-3-酮。在5-10 mol％手性磷酸的存在下，以高达99％ee的良好或高收率获得了一系列2-（2-氧代-2-苯基乙基）-2-芳基吲哚-3-酮。通过简单的修饰，可以容易地将获得的加合物转化为二氢吲哚，三环吲哚-3-酮和四环四氢吲哚并[1,2- a ]喹啉。
• Catalytic Asymmetric Mukaiyama–Mannich Reaction of Cyclic <i>C</i>-Acylimines with Difluoroenoxysilanes: Access to Difluoroalkylated Indolin-3-ones
  作者：Jin-Shan Li、Yong-Jie Liu、Guang-Wu Zhang、Jun-An Ma

  DOI：10.1021/acs.orglett.7b03213

  日期：2017.12.1

  A catalytic enantioselective Mukaiyama-Mannich reaction of cyclic C-acylimines with difluoroenoxysilanes is reported.(S)-TRIP enables the enantioselective synthesis of a series of novel difluoroalkylated indolin-3-ones bearing a quaternary stereocenter in up to 97% yield and 98% ee. The synthetic utility of this protocol is highlighted by efficient conversion of the products to the corresponding indolin-3-one derivatives without any erosion of the enantiopurity.
• TEMPO-catalyzed oxidative homocoupling route to 3,2′-biindolin-2-ones via an indolin-3-one intermediate
  作者：Bo Yin、Panpan Huang、Yingbing Lu、Liangxian Liu

  DOI：10.1039/c6ra24834a

  日期：——

  A combinative C2-selective arylation, and C3-selective carbonylation of free indole derivatives, by means of TEMPO catalysis and a silver oxidant under non-directing group conditions, was successful demonstrated. This new methodology is both atom and step efficient and is applicable to a broad scope of substrates, allowing the synthesis of a range of synthetically valuable 3,2′-biindolin-2-ones in

  成功地证明了在非定向基团条件下借助TEMPO催化和银氧化剂对游离吲哚衍生物进行的C2选择性芳基化和C3选择性羰基化。这种新方法既原子又高效，并且适用于广泛的底物，从而可以中等至极高的产率合成一系列具有合成价值的3,2'-联吲哚-2-酮。