1-苄基-3-乙基-1H-吲哚 | 17017-59-3

• 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: 1-苄基-3-乙基-1H-吲哚
• 英文名称: 1-benzyl-3-ethyl-1H-indole
• 英文别名: 1-Benzyl-3-ethylindole
• CAS: 17017-59-3
• 化学式: C₁₇H₁₇N
• 分子量: 235.329
• InChiKey: ZECLCTCZLCHYBG-UHFFFAOYSA-N

物化性质

• 熔点：
  30-32.5 °C
• 沸点：
  402.2±24.0 °C(Predicted)
• 密度：
  1.02±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 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-苄基-3-乙基-1H-吲哚 在 potassium tert-butylate 、 氧气 作用下， 以 二甲基亚砜 为溶剂， 反应 0.33h， 以99 mg的产率得到3-乙基吲哚
  参考文献：
  名称：

  钯催化的胺类脱氢生成胺。通过胺与芳肼的交叉偶联反应获得吲哚的自然路线

  摘要：

  AbstractH‐substituted imines are elusive compounds formed when aldehydes or ketones are mixed with ammonia. However, this class of molecules can be prepared through selective removal of a hydrogen molecule from a primary amine using a transition metal catalyst. This biomimetic transformation, previously employed for the N‐alkylation of anilines, is applied here to a domino preparation of differently substituted indoles from aliphatic primary amines and arylhydrazines. Several different linear and branched aliphatic primary amines are oxidized with reusable palladium on charcoal to the corresponding primary imines entrapped as arylhydrazones that can be isolated as such. Arylhydrazones can be further converted into N‐alkylindole derivatives via an acid‐mediated indolisation reaction. The one‐pot domino hydrogen transfer Fischer indole synthesis under heterogeneous catalysis is also possible, giving access to diverse substituted indoles, including NH indoles obtained after deprotection of the corresponding benzyl compounds. The truly heterogeneous nature of the catalyst was demonstrated by recycling the catalyst in the same reaction, and in other palladium‐catalysed transformations.magnified image

  DOI：

  10.1002/adsc.201300559
• 作为产物：
  描述：

  1-benzyl-2-butylidene-1-phenylhydrazine 在 zinc(II) chloride 作用下， 以 2-甲基-2-丁醇 为溶剂， 反应 3.0h， 以85%的产率得到1-苄基-3-乙基-1H-吲哚
  参考文献：
  名称：

  钯催化的胺类脱氢生成胺。通过胺与芳肼的交叉偶联反应获得吲哚的自然路线

  摘要：

  AbstractH‐substituted imines are elusive compounds formed when aldehydes or ketones are mixed with ammonia. However, this class of molecules can be prepared through selective removal of a hydrogen molecule from a primary amine using a transition metal catalyst. This biomimetic transformation, previously employed for the N‐alkylation of anilines, is applied here to a domino preparation of differently substituted indoles from aliphatic primary amines and arylhydrazines. Several different linear and branched aliphatic primary amines are oxidized with reusable palladium on charcoal to the corresponding primary imines entrapped as arylhydrazones that can be isolated as such. Arylhydrazones can be further converted into N‐alkylindole derivatives via an acid‐mediated indolisation reaction. The one‐pot domino hydrogen transfer Fischer indole synthesis under heterogeneous catalysis is also possible, giving access to diverse substituted indoles, including NH indoles obtained after deprotection of the corresponding benzyl compounds. The truly heterogeneous nature of the catalyst was demonstrated by recycling the catalyst in the same reaction, and in other palladium‐catalysed transformations.magnified image

  DOI：

  10.1002/adsc.201300559

文献信息

• Intermolecular dearomative oxidative coupling of indoles with ketones and sulfonylhydrazines catalyzed by I2: synthesis of [2,3]-fused indoline tetrahydropyridazines
  作者：Feng Wei、Liang Cheng、Hongyan Huang、Jiejie Liu、Dong Wang、Li Liu

  DOI：10.1007/s11426-016-0170-8

  日期：2016.10

  A convergent construction of [2,3]-fused indoline tetrahydropyridazines via an I2/tert-butyl hydroperoxide (TBHP) catalyzed three-component dearomative oxidative coupling of indoles, hydrazines and acetophenone was established in moderate to good yields. This protocol provides a new approach for the synthesis of these biologically interesting fused indolines.

  通过I2/叔丁基过氧化氢（TBHP）催化的吲哚、肼和乙酰苯的三组分脱芳构氧化偶联反应，实现了[2,3]-融合吲哚四氢吡啶嗪的收敛构建，产率中等至良好。该方法为这些具有生物学意义的融合吲哚的合成提供了一条新途径。
• Synthesis of Indole Derivatives by [2 + 2] Photocycloaddition of Indoline-2-thiones with alkenes and photodesulfurization of indoline-2-thiones
  作者：Takehiko Nishio、Mitsuru Oka

  DOI：10.1002/hlca.19970800205

  日期：1997.3.24

  The photochemical synthesis of indole derivatives starting from the indoline-2-thiones 1 is described. Irradiation of indoline-2-thiones 1 in the presence of alkenes 3 gave 2-alkyl-3H-indoles 4–7 or 2-alkylindoles 8–22 through the ring cleavage of the intermediates, spirocyclic amino-thietanes, initially derived by [2 + 2] cycloaddition of the CS bond of 1 and the CC bond of 3. Irradiation of 1 in

  描述了从二氢吲哚-2-硫酮1开始的吲哚衍生物的光化学合成。二氢吲哚-2-硫酮的照射1在烯烃的存在下3，得到2-烷基-3- ħ -indoles 4 - 7或2-烷基吲哚8 - 22穿过中间体的环切割，螺环氨基thietanes，最初由衍生[ [2 + 2]的1个CS键和3的CC键的环加成。在三烷基胺26存在下辐照1可获得脱硫产物27 – 32和意外的3-烷基吲哚33 – 40。Ñ -Acylindoline -2-硫酮11 - p，得到去酰基化的产品，二氢吲哚-2-硫酮1A - b，和乙酯43在CDC1照射时通过γ-H提取由激发硫代酰胺S-原子3 / EtOH或苯/乙醇 氧类似物2a - d也经过分子内H提取，以类似方式得到吲哚2-2-酮2e - f和乙酯43。
• Benzylic C(sp³)–C(sp²) cross-coupling of indoles enabled by oxidative radical generation and nickel catalysis
  作者：Weonjeong Kim、Jangwoo Koo、Hong Geun Lee

  DOI：10.1039/d0sc06666d

  日期：——

  effectively delivered from an aryl (pseudo)halide or an acid anhydride coupling partner, respectively. The developed method utilizes mild conditions and exhibits a wide substrate scope for both substituted indoles and C(sp2)-based reaction counterparts. Mechanistic studies have shown that competitive hydrogen atom transfer (HAT) processes, which are frequently encountered in conventional methods, are not

  基于吲哚底物的容易氧化事件，开发了一种机械上独特的苄基 C(sp 3 )-H 键功能化策略。这种新颖的途径是通过在底物的苄基位置上有效地产生自由基来启动的，随后通过过渡金属催化来完成整个转化。最终，芳基或酰基可以分别从芳基（拟）卤化物或酸酐偶联配偶体有效地传递。所开发的方法利用温和的条件，并对取代的吲哚和基于 C(sp 2 ) 的反应对应物表现出广泛的底物范围。机理研究表明，传统方法中经常遇到的竞争性氢原子转移（HAT）过程并不参与所开发策略的产物形成过程。
• Regioselective Inter- and Intramolecular Formal [4+2] Cycloaddition of Cyclobutanones with Indoles and Total Synthesis of (±)-Aspidospermidine
  作者：Mizuki Kawano、Takaaki Kiuchi、Shoko Negishi、Hiroyuki Tanaka、Takaya Hoshikawa、Jun-ichi Matsuo、Hiroyuki Ishibashi

  DOI：10.1002/anie.201206734

  日期：2013.1.14

  way: A formal [4+2] cycloaddition between various cyclobutanones and indoles proceeded efficiently under Lewis acid catalysis (see scheme; PG = protecting group). The regioselectivity of the reaction could be controlled in such a way that each of the two possible regioisomers of a cycloaddition product could be synthesized selectively. The usefulness of this reaction for the total synthesis of hydrocarbazole

  这种方式：在路易斯酸催化下，各种环丁酮和吲哚之间的正式[4 + 2]环加成反应有效进行（参见方案； PG =保护基）。可以以这样的方式控制反应的区域选择性，使得可以选择性地合成环加成产物的两种可能的区域异构体中的每一个。证明了该反应对于完全合成烃唑天然产物的有用性。
• Highly diastereoselective oxa-[3+3] cyclization with C,N-cyclic azomethine imines <i>via</i> the copper-catalyzed aerobic oxygenated CC bond of indoles
  作者：Lemao Yu、Yuan Zhong、Jicong Yu、Lu Gan、Zhengjun Cai、Rui Wang、Xianxing Jiang

  DOI：10.1039/c7cc09640b

  日期：——

  Herein, a copper-catalyzed highly diastereoselective aerobic oxygenated [3+3] cyclization of 3-substituted indoles with C,N-cyclic azomethine imines using oxygen as the sole oxidant under mild conditions has been developed. This protocol provides a simple and convenient approach for constructing [2,3]-fused indoline O-heterocycles bearing two pharmaceutically intriguing parts, tetrahydroisoquinoline

  在本文中，已经开发出在温和的条件下使用氧作为唯一氧化剂，用C，N-环偶氮甲亚胺将铜取代的3-取代的吲哚进行高非对映选择性好氧氧化[3 + 3]环化反应的方法。该协议为构建带有两个药学上引人入胜的部分，即四氢异喹啉和吲哚啉的[2,3]-融合的吲哚啉O-杂环提供了一种简单便捷的方法。在温和的反应条件下，观察到良好的收率和优异的非对映选择性。