2-(1-苄基-5-甲氧基-1H-吲哚-3-基)乙胺 | 40619-73-6

• 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
• 中文名称: 2-(1-苄基-5-甲氧基-1H-吲哚-3-基)乙胺
• 英文名称: 2-(1-benzyl-5-methoxy-1H-indol-3-yl)ethylamine
• 英文别名: 1-Benzyl-5-methoxy-tryptamin；1-Benzyl-5-methoxy-3-(β-amino-ethyl)-indol；2-(1-benzyl-5-methoxy-indol-3-yl)-ethylamine；2-(1-Benzyl-5-methoxy-indol-3-yl)-aethylamin；2-(1-Benzyl-5-methoxyindol-3-yl)ethanamine
• CAS: 40619-73-6
• 化学式: C₁₈H₂₀N₂O
• 分子量: 280.37
• InChiKey: BXJRLUXIZQJJTF-UHFFFAOYSA-N

物化性质

• 沸点：
  481.0±40.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  40.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(1-苄基-5-甲氧基-1H-吲哚-3-基)乙胺 在 sodium 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 氨 为溶剂， 反应 1.75h， 生成 褪黑素
  参考文献：
  名称：

  Aromatization of 1,6,7,7a-Tetrahydro-2H-indol-2-ones by a Novel Process. Preparation of Key-Intermediate Methyl 1-Benzyl-5-methoxy-1H-indole-3-acetate and the Syntheses of Serotonin, Melatonin, and Bufotenin

  摘要：

  Imine 7 of 1,4-cyclohexanedione mono-ethylene ketal 6 was reacted with maleic anhydride, affording the cyclized adduct 8. Methyl esterification of 8, accompanied by transacetalization, led to the dihydrooxindole derivative 10. Aromatization of 10 was then accomplished with POCl3, leading directly to the key-intermediate title compound 11 in 74% yield from ketone 6. Serotonin, melatonin, and bufotenin were then obtained by standard reactions.

  DOI：

  10.1021/jo0110597
• 作为产物：
  描述：

  1-苄基-5-甲氧基-1H-吲哚-3-乙酸甲酯 在 lithium aluminium tetrahydride 、 氨 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 240.0h， 生成 2-(1-苄基-5-甲氧基-1H-吲哚-3-基)乙胺
  参考文献：
  名称：

  Aromatization of 1,6,7,7a-Tetrahydro-2H-indol-2-ones by a Novel Process. Preparation of Key-Intermediate Methyl 1-Benzyl-5-methoxy-1H-indole-3-acetate and the Syntheses of Serotonin, Melatonin, and Bufotenin

  摘要：

  Imine 7 of 1,4-cyclohexanedione mono-ethylene ketal 6 was reacted with maleic anhydride, affording the cyclized adduct 8. Methyl esterification of 8, accompanied by transacetalization, led to the dihydrooxindole derivative 10. Aromatization of 10 was then accomplished with POCl3, leading directly to the key-intermediate title compound 11 in 74% yield from ketone 6. Serotonin, melatonin, and bufotenin were then obtained by standard reactions.

  DOI：

  10.1021/jo0110597

文献信息

• Gold(<scp>i</scp>)-catalyzed pathway-switchable tandem cycloisomerizations to indolizino[8,7-<i>b</i>]indole and indolo[2,3-<i>a</i>]quinolizine derivatives
  作者：Chengjun Liu、Zenghui Sun、Fukai Xie、Guoduan Liang、Lu Yang、Yaqiao Li、Maosheng Cheng、Bin Lin、Yongxiang Liu

  DOI：10.1039/c9cc05667j

  日期：——

  Experimental and theoretical explorations were performed on the pathways of the cascade cycloisomerizations of tryptamine-N-ethynylpropiolamide substrates. The methodology provided a common strategy to access either indolizino[8,7-b]indoles or indolo[2,3-a]quinolizines in a switchable fashion.

  对色胺-N-乙炔基丙酰胺酰胺底物的级联环异构化的途径进行了实验和理论探索。该方法学提供了一种通用策略，可以以可切换的方式访问吲哚并[ 8,7- b ]吲哚或吲哚[2,3- a ]喹啉。
• Ynesulfonamide-Based Silica Gel and Alumina-Mediated Diastereoselective Cascade Cyclizations to Spiro[indoline-3,3′-pyrrolidin]-2-ones under Neat Conditions
  作者：Yanshi Wang、Xiaoyu Wang、Jingsheng Lin、Bo Yao、Guanghui Wang、Yuandong Zhao、Xinhang Zhang、Bin Lin、Yang Liu、Maosheng Cheng、Yongxiang Liu

  DOI：10.1002/adsc.201701576

  日期：2018.4.3

  spiro[indoline‐3,3′‐pyrrolidin]‐2‐ones were synthesized via a silica gel and alumina‐mediated sequential transformation based on tryptamine‐derived ynesulfonamide substrates under neat conditions. The inherent tendency of C−C bond migration through Wagner‐Meerwein rearrangement in the synthesis of spirooxindole was prevented by water trapping to the spiroindoleninium intermediate. The functional group tolerances

  螺旋[二氢吲哚啉-3,3'-吡咯烷酮] -2-酮是通过硅胶和氧化铝介导的顺序转化合成的，该转化是基于纯净的色胺衍生的乙磺酰胺底物。螺线形吲哚中间体中的水被阻止，从而防止了螺线形吲哚合成中通过Wagner-Meerwein重排的C-C键迁移的固有趋势。使用多种底物研究了该方法的官能团耐受性。通过同位素标记的实验探索了顺序转化的详细机制。该策略被进一步应用在吲哚生物碱蓝藻碱和Horsfiline的正式合成中。
• Brønsted Acid-Catalyzed Tandem Cyclizations of Tryptamine-Ynamides Yielding 1<i>H</i> -Pyrrolo[2,3-<i>d</i> ]carbazole Derivatives
  作者：Yanshi Wang、Jingsheng Lin、Xiaoyu Wang、Guanghui Wang、Xinhang Zhang、Bo Yao、Yuandong Zhao、Pengfei Yu、Bin Lin、Yongxiang Liu、Maosheng Cheng

  DOI：10.1002/chem.201705189

  日期：2018.3.15

  study, 1H‐pyrrolo[2,3‐d]carbazole derivatives were synthesized by a Brønsted acid‐catalyzed tandem cyclization starting from tryptamine‐based ynamides. This strategy prevented Wagner–Meerwein rearrangement by instantaneous intramolecular nucleophilic trapping of the indoleninium to afford a tetracyclic indoline via an in situ‐formed enol species induced by the formation of a more stable conjugate diene

  酰胺作为通用的合成前体，引起了合成化学家的广泛关注，并引发了用于构建各种结构的许多方法的发展。1 H- Pyrrolo [2,3- d ]咔唑是一系列单萜吲哚生物碱的核心骨架，例如，在Kopsia，Strychnos和Aspidosperma中发现。在本研究中，1 H-吡咯并[2,3- d]咔唑衍生物是通过布朗斯台德酸催化的串联环化反应从基于色胺的乙酰胺开始合成的。该策略通过瞬时的分子内亲核捕获吲哚鎓来阻止Wagner-Meerwein重排，从而通过原位形成的烯醇物种（由更稳定的共轭二烯部分的形成诱导）提供四环吲哚啉。通过使用一系列容易获得的底物来研究官能团的耐受性。根据捕获半胱氨酸中间体的证据，提出了一种合理的机制。最后，利用我们最新开发的方法合成了Büchi酮，它是吲哚生物碱长春花碱合成中的关键中间体。
• Rh-Catalyzed [3 + 2] Cycloaddition of 1-Sulfonyl-1,2,3-triazoles: Access to the Framework of Aspidosperma and Kopsia Indole Alkaloids
  作者：Yun Li、Qingyu Zhang、Qiucheng Du、Hongbin Zhai

  DOI：10.1021/acs.orglett.6b01968

  日期：2016.8.19

  the substrate and proceeded efficiently under mild conditions. A wide range of functional groups could be tolerated. These features render the current reaction a highly useful tool for the synthesis of polycyclic indole alkaloids, as showcased by a rapid assembly of the core structure of Aspidosperma and the related alkaloids.

  已经开发了一种Rh（II）催化的涉及吲哚C2-C3碳-碳双键的脱芳香性分子内[3 + 2]偶极环加成反应。该反应从底物内的三唑部分开始，并在温和条件下有效地进行。可以容忍各种各样的官能团。这些特征使当前反应成为合成多环吲哚生物碱的高度有用的工具，如快速被孢霉和相关生物碱的核心结构组装所证明的那样。
• Synthetic Approaches to Highly Functional β-Carboline Building Blocks via Allylic Amidation
  作者：Ben Feringa、Johannes Teichert、Martín Fañanás-Mastral

  DOI：10.1055/s-0031-1289656

  日期：2012.2

  A new, straightforward synthesis of highly functional β-carboline building blocks is presented that makes use of allylic amidation methodology. The products obtained carry a terminal double bond as well as an easy-to-deprotect amide, which make them perfectly suitable for further functionalization. The use of the trifluoroacetamide group is exploited in a dual fashion; it acts as a protecting group and functions as the nucleophile for the allylic amidation reaction.

  本文介绍了一种利用烯丙基酰胺化方法直接合成高功能δ-咔啉构筑基块的新方法。获得的产物带有一个末端双键和一个易于脱保护的酰胺，这使它们非常适合进一步功能化。三氟乙酰胺基团的使用具有双重作用：既是保护基团，又是烯丙基酰胺化反应的亲核体。