4-(1H-Indol-2-yl)butanenitrile | 165532-78-5

• 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: 4-(1H-Indol-2-yl)butanenitrile
• CAS: 165532-78-5
• 化学式: C₁₂H₁₂N₂
• 分子量: 184.241
• InChiKey: ZXOVEKGZILEOEL-UHFFFAOYSA-N

物化性质

• 沸点：
  410.4±28.0 °C(Predicted)
• 密度：
  1.143±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  39.6
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-(1H-Indol-2-yl)butanenitrile 在 dirhodium(II) tetrakis(perfluorobutyrate) 氢氧化钾 、 sodium hydroxide 、 正丁基锂 、 四丁基硫酸氢铵 、 三乙胺 、 甲烷磺酰基叠氮化物 、 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 、 乙腈 、 苯 为溶剂， 反应 32.0h， 生成 4-(1-Benzenesulfonyl-1H-indol-2-yl)butyric acid 1-(methylcarbamoyl)-2-oxopropyl ester
  参考文献：
  名称：

  Intramolecular Cycloaddition of Isomunchnone Dipoles to Heteroaromatic .pi.-Systems

  摘要：

  A series of furanyl-, thienyl-, and indole-substituted diazo imides were prepared by treating the appropriate amides with diketene to give the N-acetoacylated imides. Exposure of the imides to standard diazo transfer conditions afforded the desired diazo imides. Treatment of these diazo imides bearing tethered heterocyclic rings with rhodium(II) acetate affords transient isomunchnone dipoles. The mesoionic dipoles are formed by cyclization of the rhodium carbenoid onto the neighboring amide carbonyl oxygen atom. The scope and limitations of the intramolecular 1,3-dipolar cycloaddition of the isomunchnones across a tethered furan and thiophene ring were studied. The facility of the internal cycloaddition is influenced by the length and nature of the tether connecting the dipole and dipolarophile functionalities. The reaction is critically dependent on conformational factors in the transition state. In addition, the first examples of intramolecular cycloaddition of isomunchnones to indole dipolarophiles are reported. Cycloadditions of this type generate highly functionalized polyheterocyclic systems with complete relative stereocontrol at the newly formed stereocenters.

  DOI：

  10.1021/jo00102a037
• 作为产物：
  描述：

  2-(3-hydroxypropyl)indole 在 吡啶 作用下， 以 二甲基亚砜 为溶剂， 反应 16.0h， 生成 4-(1H-Indol-2-yl)butanenitrile
  参考文献：
  名称：

  Intramolecular Cycloaddition of Isomunchnone Dipoles to Heteroaromatic .pi.-Systems

  摘要：

  A series of furanyl-, thienyl-, and indole-substituted diazo imides were prepared by treating the appropriate amides with diketene to give the N-acetoacylated imides. Exposure of the imides to standard diazo transfer conditions afforded the desired diazo imides. Treatment of these diazo imides bearing tethered heterocyclic rings with rhodium(II) acetate affords transient isomunchnone dipoles. The mesoionic dipoles are formed by cyclization of the rhodium carbenoid onto the neighboring amide carbonyl oxygen atom. The scope and limitations of the intramolecular 1,3-dipolar cycloaddition of the isomunchnones across a tethered furan and thiophene ring were studied. The facility of the internal cycloaddition is influenced by the length and nature of the tether connecting the dipole and dipolarophile functionalities. The reaction is critically dependent on conformational factors in the transition state. In addition, the first examples of intramolecular cycloaddition of isomunchnones to indole dipolarophiles are reported. Cycloadditions of this type generate highly functionalized polyheterocyclic systems with complete relative stereocontrol at the newly formed stereocenters.

  DOI：

  10.1021/jo00102a037

文献信息

• Synthesis of Indolophanes by Photochemical Macrocyclization
  作者：Magnus Pfaffenbach、Alexander Roller、Tanja Gaich

  DOI：10.1002/chem.201600835

  日期：2016.6.13

  Herein, we report the synthetically practical, short, and general access to novel indolophane architectures by means of a photochemical C−H activation process—the Witkop cyclization. These highly strained scaffolds were obtained by photoinduced ring closure and feature atropisomerism as well as aromatic ring current effects, which both have been investigated. The prevailing regioselectivity of theWitkop

  在本文中，我们报告了通过光化学CH活化过程-Witkop环化，可以合成，实用且短暂地进入新颖的吲哚烷结构。这些高度应变的支架是通过光诱导的闭环获得的，具有阻转异构性以及芳香环电流效应，这两个方面均已进行了研究。季碳中心的存在完全逆转了维特科普环化反应的主要区域选择性，对提供实验证据的系统产生了强烈的索普-英戈尔德效应。
• Dearomative Arylcyanation of Indoles via C–CN Bond Activation Enabled by Ni/Lewis Acid Cooperative Catalysis
  作者：Wen-Qian Zhang、Hong-Cheng Shen、Liu-Zhu Gong

  DOI：10.1021/acs.orglett.2c02668

  日期：2022.9.16

  acid cooperatively catalyzed intramolecular dearomative arylcyanation of indoles is presented. The reaction proceeds through a C–CN bond activation, dearomatization, and benzylic cyanation sequence, affording 3-cyano fused indolinyl heterocycles in good to excellent yields and excellent diastereoselectivity. The asymmetric version of the reaction can be established in moderate enantioselectivity by using

  提出了镍/路易斯酸协同催化吲哚分子内脱芳基芳基氰化反应。该反应通过 C-CN 键活化、脱芳构化和苄基氰化序列进行，以良好至优异的产率和优异的非对映选择性得到 3-氰基稠合的吲哚基杂环。反应的不对称形式可以通过使用手性配体以中等对映选择性建立。
• Palladium-Catalyzed Direct 2-Alkylation of Indoles by Norbornene-Mediated Regioselective Cascade C–H Activation
  作者：Lei Jiao、Thorsten Bach

  DOI：10.1021/ja2055066

  日期：2011.8.24

  A palladium-catalyzed direct 2-alkylation reaction of free N-H indoles has been developed. This reaction relies on a norbornene-mediated cascade C-H activation process at the indole ring, which features high regioselectivity and excellent functional group, tolerance. The reaction represents the first example for a generally applicable, direct C-H alkylation of indole at the 2-position.
• Regioselective Direct C–H Alkylation of NH Indoles and Pyrroles by a Palladium/Norbornene-Cocatalyzed Process
  作者：Thorsten Bach、Lei Jiao

  DOI：10.1055/s-0033-1338523

  日期：——

  Nitrogen-containing heterocycles, including 1H-indoles and electron-deficient 1H-pyrroles, undergo a palladium/norbornene-cocatalyzed regioselective alkylation at the C-H bond adjacent to the NH group. A primary alkyl halide is used as the electrophile and the reaction proceeds smoothly under mild conditions to give 2-alkyl-1H-indoles and 2-substituted or 2,3-disubstituted 5-alkyl-1H-pyrroles in good yields.
• Intramolecular Cycloaddition of Isomunchnone Dipoles to Heteroaromatic .pi.-Systems
  作者：Albert Padwa、Donald L. Hertzog、William R. Nadler

  DOI：10.1021/jo00102a037

  日期：1994.11

  A series of furanyl-, thienyl-, and indole-substituted diazo imides were prepared by treating the appropriate amides with diketene to give the N-acetoacylated imides. Exposure of the imides to standard diazo transfer conditions afforded the desired diazo imides. Treatment of these diazo imides bearing tethered heterocyclic rings with rhodium(II) acetate affords transient isomunchnone dipoles. The mesoionic dipoles are formed by cyclization of the rhodium carbenoid onto the neighboring amide carbonyl oxygen atom. The scope and limitations of the intramolecular 1,3-dipolar cycloaddition of the isomunchnones across a tethered furan and thiophene ring were studied. The facility of the internal cycloaddition is influenced by the length and nature of the tether connecting the dipole and dipolarophile functionalities. The reaction is critically dependent on conformational factors in the transition state. In addition, the first examples of intramolecular cycloaddition of isomunchnones to indole dipolarophiles are reported. Cycloadditions of this type generate highly functionalized polyheterocyclic systems with complete relative stereocontrol at the newly formed stereocenters.