N-<2-(indol-5-yl)ethyl>acetamide | 58491-47-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-<2-(indol-5-yl)ethyl>acetamide
• 英文别名: 5-(2-acetamidoethyl)indole；Acetamide, N-[2-(1H-indol-5-yl)ethyl]-；N-[2-(1H-indol-5-yl)ethyl]acetamide
• CAS: 58491-47-7
• 化学式: C₁₂H₁₄N₂O
• 分子量: 202.256
• InChiKey: WEAVAWGUFNZWDQ-UHFFFAOYSA-N

物化性质

• 沸点：
  484.7±28.0 °C(Predicted)
• 密度：
  1.164±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 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：
  44.9
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-<2-(indol-5-yl)ethyl>acetamide 生成 8-Acetyl-9-methyl-6,7,8,9-tetrahydro-3H-pyrido<3,4-e>indol
  参考文献：
  名称：

  NARUTO S.; TERADA A., CHEM. AND PHARM. BULL. , 1975, 23, NO 12, 3184-3188

  摘要：

  DOI：
• 作为产物：
  描述：

  1-乙酰基咪唑 、 1H-吲哚-5-乙胺 以 苯 为溶剂， 反应 1.5h， 以87%的产率得到N-<2-(indol-5-yl)ethyl>acetamide
  参考文献：
  名称：

  Aminoethyl-substituted indole-3-acetic acids for the preparation of tagged and carrier-linked auxin

  摘要：

  Indole-3-acetic acid is an indispensable hormone (auxin) in plants and an important metabolite in humans, animals, and microorganisms. Here we introduce its 5- and 6-(2-aminoethyl)-derivatives for use in the design of novel research tools, such as immobilized and carrier-linked forms of indole-3-acetic acid and its conjugates with biochemical tags or biocompatible molecular probes. The aliphatic nitrogens of 5- and 6-(2-aminoethyl)indole were acetylated and the products were converted to the corresponding 3-(N,N-dimethylamino)methyl derivatives (gramines). These were reacted with cyanide. Saponification of the resulting acetonitriles was accompanied by N-deprotection to yield 5- and 6-(2-aminoethyl)indole-3-acetic acids. The latter were chemically stable and could be linked, via their amino groups, and without prior protection of their carboxyl moieties, to bovine serum albumin and to biotin, including appropriate spacer modules. One of the protein conjugates was used to elicit the formation of monoclonal antibodies, which were evaluated using the biotin conjugates in an enzyme-linked immunosorbent assay employing streptavidin-coupled alkaline phosphatase, and thus shown to recognize predominantly the indole-3-acetic acid moiety. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.02.046

文献信息

• Photochemical synthesis of azepinoindoles and azocinoindoles from N-chloroacetylindolylethylamines, and a mechanistic study based on the correlation between quantum yields and calculated frontier electron densities of indole radicals.
  作者：SHUNJI NARUTO、OSAMU YONEMITSU

  DOI：10.1248/cpb.28.900

  日期：——

  On irradiation in 50% aqueous ethanol, the N-chloroacetyl derivatives of seven isomeric indolylethylamines gave the corresponding azocinoindole derivatives through photocyclization at the ortho and peri positions. Quantum yields for product formation with 2537 Å light showed the relative reactivity at each position of the indole ring to be in the order 3>6, 4>7, 2>5>1. In order to identify the reactive intermediary species and to establish the mechanism of the photocyclizations, frontier electron densities of several species of indole were calculated by CNDO/2 and INDO. The quantum yields for product formation from 1-substituted indole derivatives correlated fairly well (correlation coefficient r=0.82) with the singly occupied molecular orbitals (SOMO) electron densities (ED) of the 1-methylindole radical cation, but there was a better correlation (r=0.90) between the quantum yields for product formation from 1-unsubstituted compounds and the SOMO-ED of the indole-1-radical. These results show that the mechanism of the photocyclization of N-chloroacetylindolylethylamines involves both indole radical cations and indole-1-radicals as reactive intermediary species.

  在 50% 的乙醇水溶液中照射时，七种吲哚乙胺异构体的 N-氯乙酰基衍生物通过正位和周位的光环化反应生成相应的偶氮吲哚衍生物。在 2537 Å 光下生成产物的量子产率显示，吲哚环各位置的相对反应性依次为 3>6、4>7、2>5>1。为了确定反应的中间产物并确定光环化的机理，利用 CNDO/2 和 INDO 计算了几种吲哚的前沿电子密度。1 取代吲哚衍生物生成产物的量子产率与 1 甲基吲哚自由基阳离子的单占分子轨道（SOMO）电子密度（ED）有相当好的相关性（相关系数 r=0.82），但 1 未取代化合物生成产物的量子产率与吲哚-1-自由基的 SOMO-ED 有更好的相关性（r=0.90）。这些结果表明，N-氯乙酰吲哚乙胺的光环化机理涉及吲哚自由基阳离子和作为反应中间体的吲哚-1-自由基。
• Aminoethyl-substituted indole-3-acetic acids for the preparation of tagged and carrier-linked auxin
  作者：Nebojša Ilić、Ivan Habuš、Lana S. Barkawi、Seijin Park、Zoran Štefanić、Biserka Kojić-Prodić、Jerry D. Cohen、Volker Magnus

  DOI：10.1016/j.bmc.2005.02.046

  日期：2005.5

  Indole-3-acetic acid is an indispensable hormone (auxin) in plants and an important metabolite in humans, animals, and microorganisms. Here we introduce its 5- and 6-(2-aminoethyl)-derivatives for use in the design of novel research tools, such as immobilized and carrier-linked forms of indole-3-acetic acid and its conjugates with biochemical tags or biocompatible molecular probes. The aliphatic nitrogens of 5- and 6-(2-aminoethyl)indole were acetylated and the products were converted to the corresponding 3-(N,N-dimethylamino)methyl derivatives (gramines). These were reacted with cyanide. Saponification of the resulting acetonitriles was accompanied by N-deprotection to yield 5- and 6-(2-aminoethyl)indole-3-acetic acids. The latter were chemically stable and could be linked, via their amino groups, and without prior protection of their carboxyl moieties, to bovine serum albumin and to biotin, including appropriate spacer modules. One of the protein conjugates was used to elicit the formation of monoclonal antibodies, which were evaluated using the biotin conjugates in an enzyme-linked immunosorbent assay employing streptavidin-coupled alkaline phosphatase, and thus shown to recognize predominantly the indole-3-acetic acid moiety. (c) 2005 Elsevier Ltd. All rights reserved.
• NARUTO S.; TERADA A., CHEM. AND PHARM. BULL. <CPBT-AL>, 1975, 23, NO 12, 3184-3188
  作者：NARUTO S.、 TERADA A.

  DOI：——

  日期：——