3-乙烯基-1-甲基吲哚 | 62747-53-9

• 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
• 中文名称: 3-乙烯基-1-甲基吲哚
• 英文名称: 1-methyl-3-vinyl-1H-indole
• 英文别名: N-methyl-3-vinylindole；1-methyl-3-vinylindole；3-Ethenyl-1-methyl-1H-indole；3-ethenyl-1-methylindole
• CAS: 62747-53-9
• 化学式: C₁₁H₁₁N
• 分子量: 157.215
• InChiKey: MXLDILMYRIVLKC-UHFFFAOYSA-N

物化性质

• 沸点：
  287.7±9.0 °C(Predicted)
• 密度：
  0.97±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  3-乙烯基-1-甲基吲哚 在 正丁基锂 、 盐酸羟胺 、 sodium acetate 作用下， 以 四氢呋喃 、 邻二氯苯 为溶剂， 生成 N₉-methylharmane
  参考文献：
  名称：

  Efficient one-pot synthesis of anti HIV and antitumor compounds: harman and substituted harmans

  摘要：

  Anti HIV and antitumor compounds, harman and substituted harmans have been synthesized using electrocyclization reactions as key steps. A one-pot reaction sequence was used to furnish these compounds in good overall yield. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01046-3
• 作为产物：
  描述：

  (E)-1-Methyl-3-(β-methoxyvinyl)indole 在 正丁基锂 、 氧气 、 tetraphenylporphyrin 作用下， 以 四氢呋喃 、 正己烷 、 氯仿 为溶剂， 反应 3.33h， 生成 3-乙烯基-1-甲基吲哚
  参考文献：
  名称：

  Sensitized photooxygenations of 3-vinylindole derivatives

  摘要：

  A series of 1-methyl- and 1-(phenylsulfonyl)-substituted 3-vinylindoles with different electronic and steric features has been synthesized and their sensitized photooxygenation in aprotic solvents investigated. 1-Methyl-3-vinyl- (1a), 1,2-dimethyl-3-vinyl- (1b), 1-methyl-3-(beta-methoxyvinyl)- (4-Z and 4-E), 1-(phenylsulfonyl)-3-vinyl- (8a), 1-(phenylsulfonyl)-3-(alpha-methylvinyl) (8b), 1-(phenylsulfonyl)-3-(8-methoxyvinyl)- (8c and 8d), and cis-1-(phenylsulfonyl)-3-(alpha-methyl-beta-methoxyvinyl) indoles (15-Z) react with O-1(2) predominantly to give endoperoxides via [4+2] cycloaddition. However, 1,2-dimethyl-3-(beta-methoxyvinyl)indole (1c) gives [2 + 2] cycloaddition with the 3-double bond to give 1,2-dimethyl-3-formylindole (3c); trans-1-(phenylsulfonyl)-3-(alpha-methyl-beta-methoxyvinyl)indole (15-E) gives the 3-indolyl allylic hydroperoxide (17) via ene reaction, along with a small amount of isomerization of the 3-vinyl double bond. A zwitterionic intermediate in the isomerization is proposed. Most of the resulting dioxacarbazole endoperoxides are isolable and inert to reduction by trimethyl phosphite and thiourea except for N-methyldioxacarbazole 5, which undergoes clean rearrangement to indolin-2-one epoxide 7 at -20-degrees-C.

  DOI：

  10.1021/jo00079a032

文献信息

• [EN] MYOGLOBIN-BASED CATALYSTS FOR CARBENE TRANSFER REACTIONS<br/>[FR] CATALYSEURS À BASE DE MYOGLOBINE POUR RÉACTIONS DE TRANSFERT DE CARBÈNE
  申请人：UNIV ROCHESTER

  公开号：WO2016086015A1

  公开（公告）日：2016-06-02

  Methods are provided for carrying out carbene transfer transformations such as olefin cyclopropanation reactions, carbene heteroatom-H insertion reactions (heteroatom = N, S, Si), sigmatropic rearrangement reactions, and aldehyde olefination reactions with high efficiency and selectivity by using a novel class of myoglobin-based biocatalysts. These methods are useful for the synthesis of a variety of organic compounds which contain one or more new carbon-carbon or carbon-heteroatom (N, S, or Si) bond. The methods can be applied for conducting these transformations in vitro (i.e., using the biocatalyst in isolated form) and in vivo (i.e., using the biocatalyst in a whole cell system).

  提供了一种方法来进行碳烯转移反应，如烯烃环丙烷化反应，碳烯杂原子-H插入反应（杂原子= N，S，Si），σ迁移重排反应和醛烯化反应，通过使用一种新型的基于肌红蛋白的生物催化剂，可以高效和选择性地进行。这些方法对于合成含有一个或多个新碳-碳或碳-杂原子（N，S或Si）键的各种有机化合物非常有用。这些方法可以应用于体外（即使用分离形式的生物催化剂）和体内（即在整个细胞系统中使用生物催化剂）进行这些转化。
• Visible-Light-Promoted Regioselective 1,3-Fluoroallylation of <i>gem</i>-Difluorocyclopropanes
  作者：Haidong Liu、Yi Li、Ding-Xing Wang、Meng-Meng Sun、Chao Feng

  DOI：10.1021/acs.orglett.0c03268

  日期：2020.11.6

  A strategically novel protocol for ring-opening functionalization of aryl gem-difluorocyclopropanes (F2CPs), which allows an expedient construction of CF3-containing architectures via visible-light-promoted F-nucleophilic attack manifold, was disclosed. Single electron oxidation of F2CPs was ascribed as the critical step for the success of this transformation by prompting F-nucleophilic attack, as

  公开了用于芳基宝石-二氟环丙烷（F 2 CP）的开环官能化的策略上新颖的协议，其允许通过可见光促进的F-亲核攻击歧管方便地构建含CF 3的结构。F 2 CP的单电子氧化被认为是通过促进F亲核攻击以及随之而来的C–C键断裂而成功实现该转化的关键步骤。通过调用宝石-二氟取代基的阳离子稳定性质，以及通过形成CF 3获得的热力学增益，可以合理化观察到的对于该反应中的氟掺入的区域选择性。功能。通过使用经济有效的氟化试剂和易于获得的底物，可以以通常良好的收率获得广泛的结构多样化的α-烯丙基-β-三氟甲基乙苯衍生物。进一步的机械研究证明，苄基自由基中间体参与了该转化。
• Highly Efficient Hydrogen-Bonding Catalysis of the Diels–Alder Reaction of 3-Vinylindoles and Methyleneindolinones Provides Carbazolespirooxindole Skeletons
  作者：Bin Tan、Gloria Hernández-Torres、Carlos F. Barbas

  DOI：10.1021/ja203812h

  日期：2011.8.17

  Carbazolespirooxindole derivatives were synthesized in a high-yielding, atypically rapid, stereocontrolled Diels-Alder reaction catalyzed by a C(2)-symmetric bisthiourea organocatalyst. Simple precursors and mild conditions were used to construct carbazolespirooxindole derivatives with high enantiopurity and structural diversity under H-bonding catalysis. The practical approach recycles the organocatalyst

  Carbazolespirooxindole 衍生物是在由 C(2)-对称双硫脲有机催化剂催化的高产、非典型快速、立体控制的 Diels-Alder 反应中合成的。利用简单的前体和温和的条件，在氢键催化下构建了具有高对映体纯度和结构多样性的咔唑-螺环吲哚衍生物。实用的方法是循环使用有机催化剂和溶剂。这种简单而有效的操作程序将允许对这类有趣的化合物进行面向多样性的合成。
• Enantioselective Construction of Silicon-Stereogenic Silanes by Scandium-Catalyzed Intermolecular Alkene Hydrosilylation
  作者：Gu Zhan、Huai-Long Teng、Yong Luo、Shao-Jie Lou、Masayoshi Nishiura、Zhaomin Hou

  DOI：10.1002/anie.201807493

  日期：2018.9.17

  The catalytic asymmetric construction of silicon‐stereogenic silanes is of great interest and significance, but has met with only limited success to date. We herein report the enantioselective hydrosilylation of alkenes with dihydrosilanes by a chiral half‐sandwich scandium catalyst, which constitutes an efficient and general route for the synthesis of a wide range of enantioenriched silicon‐stereogenic

  固硅硅烷的催化不对称结构具有极大的意义和意义，但迄今为止仅取得了有限的成功。我们在此报告了通过手性半三明治scan催化剂与二氢硅烷进行烯烃的对映选择性氢化硅烷化反应，这是从易于获得的起始原料合成各种对映体富集的硅立体异构硅烷的有效且通用的途径。该反应具有广泛的底物范围，高收率和高对映选择性的特征。一些手性叔硅烷产物也被转化为有价值的衍生物，例如手性硅烷醇，季硅烷和苯甲酚化合物。
• N-Heterocyclic Carbene Ligand-Controlled Regioselectivity for Nickel-Catalyzed Hydroarylation of Vinylarenes with Benzothiazoles
  作者：Rui-Peng Li、Zheng-Wang Shen、Qin-Jia Wu、Jie Zhang、Hong-Mei Sun

  DOI：10.1021/acs.orglett.9b01645

  日期：2019.7.5

  A facile regioselective switch for nickel-catalyzed hydroarylation of vinylarenes with benzothiazoles has been developed, which relies on the simple structural variation of novel Ni(II) complexes of the type Ni(NHC)[P(OR)3]Br2. Using magnesium turnings as the reductant, Ni(IMes)[P(OEt)3]Br2 afforded branched products, while Ni(IPr*OMe)[P(OEt)3]Br2 created steric demand to afford linear products. This

  已开发了一种简便的区域选择性开关，用于镍催化乙烯基芳烃与苯并噻唑的氢芳基化反应，该反应依赖于Ni（NHC）[P（OR）3 ] Br 2型新型Ni（II）配合物的简单结构变化。使用镁屑作为还原剂，Ni（IMes）[P（OEt）3 ] Br 2提供支链产物，而Ni（IPr * OMe）[P（OEt）3 ] Br 2产生空间需求以提供线性产物。这项工作还提供了一个合理设计杂合Ni（II）配合物的罕见例子，该配合物通过NHC和亚磷酸酯配体之间的协同作用表现出所需的空气稳定性，反应性和区域选择性。