1-Indolecarboxylic acid anhydride | 109241-96-5

• 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: 1-Indolecarboxylic acid anhydride
• 英文别名: N-carboxyindole anhydride；indole-1-carboxylic acid anhydride；Indole-1-carbonyl indole-1-carboxylate
• CAS: 109241-96-5
• 化学式: C₁₈H₁₂N₂O₃
• 分子量: 304.305
• InChiKey: GQOYHZXBKVIADF-UHFFFAOYSA-N

物化性质

• 沸点：
  514.3±33.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  53.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-Indolecarboxylic acid anhydride 在 ammonium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 以79%的产率得到1H-吲哚-1-甲酰胺
  参考文献：
  名称：

  Indole N-carbonyl compounds: preparation and coupling of indole-1-carboxylic acid anhydride

  摘要：

  DOI：

  10.1021/jo00226a044
• 作为产物：
  描述：

  indole-1-carboxylic acid 在 N,N'-二异丙基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 生成 1-Indolecarboxylic acid anhydride
  参考文献：
  名称：

  血小板活化因子中的构效关系。第14部分：具有双重抗PAF和抗HIV-1活性的哌嗪衍生物的合成和生物学评估。

  摘要：

  随着与HIV相关的痴呆症的患病率随着受HIV感染者的寿命而增加，因此非常需要针对中枢神经系统的抗逆转录病毒和抗炎药。血小板激活因子是炎症的介质，是受感染的大脑中分泌的一种HIV诱导的神经毒素。在这项工作中，我们开发了带有杂环部分的哌嗪衍生物作为PAF拮抗剂和具有微摩尔效价的HIV-1复制抑制剂。

  DOI：

  10.1016/j.bmc.2006.07.043

文献信息

• Removable Groups for Activation of Indole Photochemistry
  作者：Alan C. Weedon、Boke Zhang

  DOI：10.1055/s-1992-34165

  日期：——

  The ability of a series of nitrogen-substituents to activate the cycloaddition photochemistry of indoles has been examined; the N-substituents were chosen in order to enable their removal following cycloaddition under mild neutral, acidic or basic conditions. N-Substituted indoles, 1a-g, were prepared in which the N-substituent is COPh, CO2Et, CO2CH2CH2SiMe3, CO2CH2CH2CN, CO2Bu-t, CO2Ph, and CO2CH2Ph, respectively. Under direct irradiation with ultraviolet light the photochemical cycloaddition reaction of compounds 1a-g with cyclopentene yields cyclobutane fused indolines resulting from bonding of the alkene termini to the 2- and 3-positions of the indole. The reaction proceeds with chemical yields in the range 32%-80% and photochemical efficiencies in the range 0.00028-0.054. When the reaction is sensitized with acetophenone the chemical yields are raised to 64-95%. This improvement arises from avoidance of competing singlet excited state derived photo-Fries rearrangement. The silyl ethoxycarbonyl group of photoadducts derived from 1c can be removed by treatment of the adduct with fluoride ion in dichloromethane, the tert-butyloxycarbonyl group of adducts derived from 1e by treatment with trifluoroacetic acid at room temperature, the benzyloxycarbonyl group of adducts derived from 1g by hydrogenolysis, and the cyanoethoxycarbonyl group of adducts derived from 1d with alcoholic carbonate at room temperature. All of these deprotection reactions proceed in very high yield. Removal of the phenoxycarbonyl group of adducts derived from 1f and the ethoxycarbonyl group of adducts derived from 1b required treament with hot concentrated base and the yields were lower, while the benzoyl group of adducts derived from 1a was stable to hot concentrated acid or base and could be removed only by treatment with lithium aluminum hydride.

  我们研究了一系列氮取代基激活吲哚环化光化学反应的能力；选择这些氮取代基是为了使它们能够在温和的中性、酸性或碱性条件下进行环化反应后被去除。 我们制备了 N 取代吲哚 1a-g，其中 N 取代基分别为 COPh、CO2Et、CO2CH2CH2SiMe3、CO2CH2CH2CN、CO2Bu-t、CO2Ph 和 CO2CH2Ph。在紫外线的直接照射下，化合物 1a-g 与环戊烯发生光化学环化加成反应，生成环丁烷融合吲哚，这是由于烯的末端与吲哚的 2-位和 3-位键合。该反应的化学收率在 32%-80% 之间，光化学效率在 0.00028-0.054 之间。当反应用苯乙酮敏化时，化学收率提高到 64-95%。这种改进是由于避免了竞争单激发态衍生的光-弗里斯重排。用氟离子在二氯甲烷中处理由 1c 生成的光加合物，可以去除其中的硅乙氧基羰基；用三氟乙酸在室温下处理由 1e 生成的加合物，可以去除其中的叔丁氧基羰基；用氢解法去除由 1g 生成的加合物中的苄氧基羰基；用碳酸醇在室温下处理由 1d 生成的加合物中的氰乙氧基羰基。所有这些脱保护反应的产率都非常高。去除 1f 衍生的加合物中的苯氧羰基和 1b 衍生的加合物中的乙氧羰基需要用热浓碱处理，收率较低，而 1a 衍生的加合物中的苯甲酰基对热浓酸或碱都很稳定，只有用氢化铝锂处理才能去除。
• Intramolecular Photochemical Cycloaddition Reactions of N-[(.omega.-Alkenyloxy)carbonyl]indoles and N-(.omega.-Alkenoyl)indoles
  作者：David L. Oldroyd、Alan C. Weedon

  DOI：10.1021/jo00085a022

  日期：1994.3

  Ultraviolet light irradiation of N-(but-3'-enoyl)indole (3i), N-(pent-4'-enoyl)indole (3j), and N-(hex-5'-enoyl) indole (3k) affords intramolecular photocycloadducts 17a-19a in which the termini of the side-chain alkene have become bonded to the 2- and 3-positions of the indole ring. The regiochemistry of the addition of the alkene is the opposite to that obtained in the corresponding intermolecular reaction of an N-acylindole with a monosubstituted alkene. The length of the methylene linkage between the tethered alkene and the N-acyl activating group in these N-alkenoylindoles affects the quantum efficiency of intramolecular cycloaddition as well as the ability of the reaction to compete with intermolecular cycloaddition in the presence of added cyclopentene. In contrast, the N-(omega-alkenyloxycarbonyl)indoles 3a-e are relatively photostable, apparently because they are frozen in an unreactive conformation for the duration of the excited state lifetime. Compounds 3a-e are, however, capable of undergoing intermolecular photocycloaddition in the presence of added alkenes and they also photodimerize. These reaction pathways dominate when lower energy wavelengths (lambda>300 nm) of ultraviolet light are used; irradiations performed at higher, energy wavelength (254 nm) give predominantly photo-Fries rearrangement products.
• BOGER, DALE L.;PATEL, MONA, J. ORG. CHEM., 52,(1987) N 17, 3934-3936
  作者：BOGER, DALE L.、PATEL, MONA

  DOI：——

  日期：——
• Structure–activity relationships in platelet-activating factor. Part 14: Synthesis and biological evaluation of piperazine derivatives with dual anti-PAF and anti-HIV-1 activity
  作者：Wafa Sallem、Nawal Serradji、Nathalie Dereuddre-Bosquet、Georges Dive、Pascal Clayette、Françoise Heymans

  DOI：10.1016/j.bmc.2006.07.043

  日期：2006.12

  drugs targeting the central nervous system. Platelet-activating factor, a mediator of inflammation, is an HIV-induced neurotoxin secreted in the infected brain. In this work, we developed piperazine derivatives bearing a heterocyclic moiety as PAF-antagonists and HIV-1 replication inhibitors with micromolar potency.

  随着与HIV相关的痴呆症的患病率随着受HIV感染者的寿命而增加，因此非常需要针对中枢神经系统的抗逆转录病毒和抗炎药。血小板激活因子是炎症的介质，是受感染的大脑中分泌的一种HIV诱导的神经毒素。在这项工作中，我们开发了带有杂环部分的哌嗪衍生物作为PAF拮抗剂和具有微摩尔效价的HIV-1复制抑制剂。
• Indole N-carbonyl compounds: preparation and coupling of indole-1-carboxylic acid anhydride
  作者：Dale L. Boger、Mona Patel

  DOI：10.1021/jo00226a044

  日期：1987.8