Indole-1-carboxylic acid (Z)-but-2-enyl ester | 155624-15-0

• 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: Indole-1-carboxylic acid (Z)-but-2-enyl ester
• 英文别名: [(Z)-but-2-enyl] indole-1-carboxylate
• CAS: 155624-15-0
• 化学式: C₁₃H₁₃NO₂
• 分子量: 215.252
• InChiKey: FMXZBCXKOROVSK-IHWYPQMZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  31.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Indole-1-carboxylic acid (Z)-but-2-enyl ester 以 苯 为溶剂， 生成 [(E)-but-2-enyl] indole-1-carboxylate
  参考文献：
  名称：

  Intramolecular Photochemical Cycloaddition Reactions of N-[(.omega.-Alkenyloxy)carbonyl]indoles and N-(.omega.-Alkenoyl)indoles

  摘要：

  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.

  DOI：

  10.1021/jo00085a022
• 作为产物：
  描述：

  顺式-2-丁烯-1-醇 、 1-Indolecarboxylic acid anhydride 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以25%的产率得到Indole-1-carboxylic acid (Z)-but-2-enyl ester
  参考文献：
  名称：

  Intramolecular Photochemical Cycloaddition Reactions of N-[(.omega.-Alkenyloxy)carbonyl]indoles and N-(.omega.-Alkenoyl)indoles

  摘要：

  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.

  DOI：

  10.1021/jo00085a022

文献信息

• 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.