1,1-dimethyl-2-phenyl-1H-benzo[e]indole | 1454914-67-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1,1-dimethyl-2-phenyl-1H-benzo[e]indole
• 英文别名: 1,1-Dimethyl-2-phenylbenzo[e]indole
• CAS: 1454914-67-0
• 化学式: C₂₀H₁₇N
• 分子量: 271.362
• InChiKey: VOPUSWCDCFQDBV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  12.4
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1,1-dimethyl-2-phenyl-1H-benzo[e]indole 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 5.0h， 以66%的产率得到1,1-dimethyl-2-phenyl-2,3-dihydro-1H-benzo[e]indole
  参考文献：
  名称：

  Single-Operation Deracemization of 3H-Indolines and Tetrahydroquinolines Enabled by Phase Separation

  摘要：

  The single-operation deracemization of 3H indolines and tetrahydroquinolines is described. An asymmetric redox approach was employed, in which a phosphoric acid catalyst, oxidant, and reductant are present in the reaction mixture. The simultaneous presence of both oxidant and reductant was enabled by phase separation and resulted in the isolation of highly enantioenriched starting materials in high yields.

  DOI：

  10.1021/ja4082827
• 作为产物：
  描述：

  1-萘肼盐酸盐 、 异丁酰苯 在 溶剂黄146 作用下， 反应 16.0h， 以40%的产率得到1,1-dimethyl-2-phenyl-1H-benzo[e]indole
  参考文献：
  名称：

  Single-Operation Deracemization of 3H-Indolines and Tetrahydroquinolines Enabled by Phase Separation

  摘要：

  The single-operation deracemization of 3H indolines and tetrahydroquinolines is described. An asymmetric redox approach was employed, in which a phosphoric acid catalyst, oxidant, and reductant are present in the reaction mixture. The simultaneous presence of both oxidant and reductant was enabled by phase separation and resulted in the isolation of highly enantioenriched starting materials in high yields.

  DOI：

  10.1021/ja4082827

文献信息

• Preparation of Indolenines via Nucleophilic Aromatic Substitution
  作者：Florian Huber、Joel Roesslein、Karl Gademann

  DOI：10.1021/acs.orglett.9b00489

  日期：2019.4.19

  An unusual aromatic substitution to access indolenines is described. 2-(2-Methoxyphenyl)acetonitrile derivatives are reacted with various alkyl and aryl Li reagents to furnish the corresponding indolenine products, constituents of natural products, and cyanine dyes such as indocyanine green. This new method was used to synthesize 41 indolenines with large functional group tolerance, and selected examples

  描述了一种不寻常的芳族取代基来取代吲哚。使2-（2-甲氧基苯基）乙腈衍生物与各种烷基和芳基Li试剂反应以提供相应的吲哚烯产物，天然产物的成分和花青染料，例如吲哚花青绿。该新方法用于合成具有较大官能团耐受性的41种吲哚胺，并将选定的实例进一步转化为相应的吲哚啉染料。关键实验提供了这种亲核芳族取代机理的见解。
• Rh(III)‐Catalyzed Cascade Cyclization of 2‐Aryl‐3<i>H</i>‐indoles and CF₃‐Imidoyl Sulfoxonium Ylides Toward Trifluoroacetimidoyl‐Substituted 11<i>H</i>‐Isoindolo[2,1‐a]indoles
  作者：Zuguang Yang、Pinyi Li、Zhengkai Chen、Xiao‐Feng Wu

  DOI：10.1002/adsc.202301036

  日期：2023.11.21

  A rhodium(III)‐catalyzed C−H activation/[4+1] annulation of 2‐aryl‐3H‐indoles and CF₃‐substituted imidoyl sulfoxonium ylides (TFISYs) has been achieved, producing a wide variety of trifluoroacetimidoyl‐substituted 11H‐isoindolo[2,1‐a]indoles in 51–86% yields. The cascade reaction involves C−H imidoylmethylation, tautomerization and AgOAc‐mediated C−N bond formation sequence. The reaction could be scaled up to 2 mmol scale.

  摘要 在铑(III)催化下，实现了 2-芳基-3H-吲哚和 CF3 取代的亚胺酰亚磺酰基（TFISYs）的 C-H 活化/[4+1]环化反应，以 51-86% 的产率生成了多种三氟乙酰亚胺酰取代的 11H-异吲哚并[2,1-a]吲哚。级联反应包括 C-H 亚胺酰甲基化、共聚和 AgOAc 介导的 C-N 键形成顺序。该反应的规模可扩大到 2 毫摩尔。
• Rh(III)-Catalyzed Successive C–H Activations of 2-Phenyl-3<i>H</i>-indoles and Cyclization Cascades to Construct Highly Fused Indole Heteropolycycles
  作者：Ju Gao、Keyu Luo、Xiaohui Wei、Hao Wang、Hong Liu、Yu Zhou

  DOI：10.1021/acs.orglett.3c00445

  日期：2023.5.19

  Rh(III)-catalyzed successive C–H activations of 2-phenyl-3H-indoles and cyclization cascades with diazo compounds were developed to construct highly fused indole heteropolycycles with a broad range of substrates and good yields. In particular, this transformation included two successive C–H activations and unusual [3+3] and [4+2] sequential cyclization cascades, in which the diazo compound played a

  研发了 Rh(III) 催化的 2-phenyl-3 H-吲哚的连续 C-H 活化和与重氮化合物的环化级联，以构建具有广泛底物和良好产率的高度稠合的吲哚杂多环。特别是，这种转化包括两个连续的 C-H 活化和不寻常的 [3+3] 和 [4+2] 顺序环化级联，其中重氮化合物在两个环化过程中发挥不同的作用，同时形成高度融合的具有新季碳中心的多环吲哚支架。
• Ir-catalyzed asymmetric hydrogenation of 2-Aryl-3H-indoles with chiral phosphine-phosphoramidite ligands
  作者：Haiyan Cao、Mingdong Zhou、Hang Yin、Kaikai Zheng、Zheng Zhang、Qiucen Shuai、Ruitong Guan、Kangjun Wang、Ying Yang、Jin Guan、Xinhu Hu

  DOI：10.1016/j.jorganchem.2023.122953

  日期：2024.1

  An asymmetric synthesis of indolines has been described by using an Ir-catalyzed asymmetric hydrogenation of 2-aryl-3H-indoles with unsymmetrical hybrid chiral phosphine-phosphoramidite ligands. The result indicated that the catalytic performance could be significantly improved by the H8-binaphthyl moiety on this ligand motif. This method is characterized by a high asymmetric induction and a reasonable

  通过使用不对称杂化手性膦-亚磷酰胺配体对 2-芳基-3 H-吲哚进行 Ir 催化不对称氢化，描述了二氢吲哚的不对称合成。结果表明，该配体基序上的H 8 -联萘基部分可以显着提高催化性能。该方法具有高度不对称诱导和合理的官能团耐受性的特点，从而为手性二氢吲哚及其衍生物提供了一种简洁有效的方法，其ee高达94%。