1-methyl-3-(pent-4-enyl)-1H-indole | 458529-77-6

• 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: 1-methyl-3-(pent-4-enyl)-1H-indole
• 英文别名: N-methyl-3-(4-pentenyl)indole；1-methyl-3-(4-pentene)indole；1-Methyl-3-pent-4-enylindole
• CAS: 458529-77-6
• 化学式: C₁₄H₁₇N
• 分子量: 199.296
• InChiKey: PGSQZWFKMCVDDF-UHFFFAOYSA-N

物化性质

• 沸点：
  324.3±11.0 °C(Predicted)
• 密度：
  0.94±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 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：

  1-methyl-3-(pent-4-enyl)-1H-indole 在 ruthenium trichloride silver trifluoromethanesulfonate 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 24.0h， 以65%的产率得到1,2,3,4-tetrahydro-1,9-dimethylcarbazole
  参考文献：
  名称：

  Ru(III)-Catalyzed Cyclization of Arene-Alkene Substrates via Intramolecular Electrophilic Hydroarylation

  摘要：

  We herein report that RuCl3/AgOTf has proven to be a hydroarylation catalyst with an efficiency and scope superior to previously known methods. This catalyst demonstrated consistent performance with arene-ene substrates of diverse structural features, providing good to excellent yields of cyclization products (chromanes, tetralins, terpenoids, dihydrocoumarins).

  DOI：

  10.1021/ol036385i
• 作为产物：
  描述：

  5-溴-1-戊烯 在 甲基碘化镁 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醚 、 苯 为溶剂， 反应 29.75h， 生成 1-methyl-3-(pent-4-enyl)-1H-indole
  参考文献：
  名称：

  Ru(III)-Catalyzed Cyclization of Arene-Alkene Substrates via Intramolecular Electrophilic Hydroarylation

  摘要：

  We herein report that RuCl3/AgOTf has proven to be a hydroarylation catalyst with an efficiency and scope superior to previously known methods. This catalyst demonstrated consistent performance with arene-ene substrates of diverse structural features, providing good to excellent yields of cyclization products (chromanes, tetralins, terpenoids, dihydrocoumarins).

  DOI：

  10.1021/ol036385i

文献信息

• Site‐Fixed Hydroboration of Terminal and Internal Alkenes using BX ₃ / ^<i>i</i> Pr ₂ NEt**
  作者：Sida Li、Chenyang Hu、Xin Cui、Jiong Zhang、Liu Leo Liu、Lipeng Wu

  DOI：10.1002/anie.202111978

  日期：2021.12.6

  A novel and general method for the hydroboration of alkenes, including aryl alkenes, 1,1-disubstituted alkenes, aliphatic alkenes, and bio-derived alkenes, using BX3 as the boration reagent in the presence of iPr2NEt is reported. The reaction was also applied to the synthesis of linear and branched 1,n-diborylalkanes. The reaction is thought to proceed by a frustrated Lewis pair type single-electron-transfer

  报道了一种在i Pr 2 NEt存在下使用 BX 3作为硼酸化试剂对烯烃（包括芳基烯烃、1,1-二取代烯烃、脂肪族烯烃和生物衍生烯烃）进行硼氢化的新型通用方法。该反应还用于合成直链和支链 1, n-二硼基烷烃。该反应被认为是通过受挫的路易斯对型单电子转移机制进行的。
• Convenient Preparation of Indolyl Malonates via Carbenoid Insertion
  作者：Romelo Gibe、Michael A. Kerr

  DOI：10.1021/jo025851z

  日期：2002.8.1

  under catalysis by rhodium(II)acetate, undergo C-H and N-H insertion reactions regioselectively depending on the substitution pattern on the indole moiety. In indoles where the 3-position is unsubstituted, high yields of the C3-H insertion product were observed. In 3-alkylindoles, 2-substitution predominated, while N-methyltetrahydrocarbazole yielded the product resulting from insertion into the C6-H bond

  吲哚类化合物，在乙酸铑（II）的催化下，用重氮马来酸甲酯处理时，会根据吲哚部分的取代方式进行区域选择性的CH和NH插入反应。在3-位未被取代的吲哚中，观察到高产率的C3-H插入产物。在3-烷基吲哚中，2-取代占主导，而N-甲基四氢咔唑则由于插入C6-H键而产生产物。氮未被保护的吲哚产生不同程度的NH插入。
• Synthesis of Complex Tetracyclic Fused Scaffolds Enabled by (3 + 2) Cycloaddition
  作者：Vincent Porte、Branca C. van Veen、Haoqi Zhang、Paolo Piacentini、Sergio Armentia Matheu、Sophie Woolford、Kevin R. Sokol、Saad Shaaban、Harald Weinstabl、Nuno Maulide

  DOI：10.1021/acs.orglett.4c01269

  日期：2024.6.14

  We describe the single-step formation of complex tetracyclic fused scaffolds enabled by (3 + 2) cycloaddition of azomethine ylides. Various indoles, N-protecting groups, and amino acids are well tolerated. The products are obtained in a catalyst-free manner with moderate to excellent yield and high diastereoselectivity. Representing a new scaffold that is not yet found in nature, the construction of

  我们描述了通过偶氮甲碱叶立德的（3+2）环加成实现复杂四环稠合支架的一步形成。各种吲哚、N-保护基团和氨基酸均具有良好的耐受性。产物以无催化剂的方式获得，具有中等至优异的产率和高非对映选择性。吡咯烷稠合环庚基、氮杂环庚烷或氧杂吲哚的构建代表了自然界中尚未发现的新支架，在新的假天然产物的合成中具有重要价值。
• Ru-Catalyzed Tandem Cross-Metathesis/Intramolecular-Hydroarylation Sequence
  作者：Jia-Rong Chen、Chang-Feng Li、Xiao-Lei An、Ji-Ji Zhang、Xiao-Yu Zhu、Wen-Jing Xiao

  DOI：10.1002/anie.200705194

  日期：2008.3.14
• CN113880871
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  公开号：——

  公开（公告）日：——