1-(indol-1-yl)but-3-en-1-one | 145291-76-5

• 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-(indol-1-yl)but-3-en-1-one
• 英文别名: 1-Indol-1-ylbut-3-en-1-one
• CAS: 145291-76-5
• 化学式: C₁₂H₁₁NO
• 分子量: 185.225
• InChiKey: VNMIHWKBZHWUDU-UHFFFAOYSA-N

物化性质

• 沸点：
  290.2±19.0 °C(Predicted)
• 密度：
  1.05±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  22
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(indol-1-yl)but-3-en-1-one 以 苯 为溶剂， 以29%的产率得到(8S,10R,13S)-1-azatetracyclo[6.4.1.02,7.010,13]trideca-2,4,6-trien-12-one
  参考文献：
  名称：

  Intramolecular photochemical cycloadditions of N-alkenyloxycarbonylindoles and N-alkenoylindoles

  摘要：

  N-烯酰基吲哚的紫外光照射可形成具有与相应的分子间反应相反的区域化学性质的分子内[2 + 2]光环加成产物；相比之下，N-烯基氧羧基吲哚似乎相对光稳定，因为它们在激发态寿命内保持在一个不活泼的构象中。

  DOI：

  10.1039/c39920001491
• 作为产物：
  描述：

  吲哚啉 在 potassium carbonate 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 水 、 丙酮 、 甲苯 为溶剂， 反应 12.0h， 生成 1-(indol-1-yl)but-3-en-1-one
  参考文献：
  名称：

  可持续的自由基级联反应合成二氟烷基化的吡咯并[1,2- a ]吲哚

  摘要：

  我们在此公开了N-（丁-2-烯酰基）吲哚具有宽的底物范围的光催化二氟烷基化和环化级联反应，其分离产率高达90％。该方法提供了在温和条件下可持续有效地合成具有季碳中心的二氟烷基化吡咯并[1,2- a ]吲哚的方法。

  DOI：

  10.1021/acs.joc.7b03017

文献信息

• NOVEL INDOLIC DERIVATIVES, THEIR PREPARATION PROCESSES AND THEIR USES IN PARTICULAR AS ANTIBACTERIALS
  申请人：Denis Jean-Noel Marie Leon

  公开号：US20100144726A1

  公开（公告）日：2010-06-10

  The invention relates to the use of at least one compound of the formula (I), in which R and R 3 are particularly a hydrogen atom, R 1 is particularly a hydrogen atom or a methyl, ethyl or isobutyl mi group, R 4 , R 5 , R 6 and R 7 are independently a hydrogen atony, an alkoxyl group with 1 to 7 carbon atoms or a halogen atom, R 2 is a hydrogen atom, an O − group or an OH group, B is an N-GP 1 or NR c , group, GP 1 being a Boc or Cbz group, and R c is a hydrogen atom or a methyl or t-butyl group, for preparing a drug for treating conditions associated with bacterial infections, in particular for treating bacterial diseases.

  该发明涉及使用至少一种具有以下式（I）的化合物，其中R和R3特别是氢原子，R1特别是氢原子或甲基、乙基或异丁基mi基团，R4、R5、R6和R7独立地是氢原子、具有1至7个碳原子的烷氧基团或卤原子，R2是氢原子、O−基团或OH基团，B是N-GP1或NRc基团，GP1是Boc或Cbz基团，Rc是氢原子或甲基或叔丁基基团，用于制备用于治疗与细菌感染相关的疾病症状的药物，特别是用于治疗细菌性疾病。
• Indole and Pyrrole Derivatives as Pre-photocatalysts and Substrates in the Sulfonyl Radical-Triggered Relay Cyclization Leading to Sulfonylated Heterocycles
  作者：Ran Yang、Dong Yi、Kunrong Shen、Qiang Fu、Jun Wei、Ji Lu、Lin Yang、Li Wang、Siping Wei、Zhijie Zhang

  DOI：10.1021/acs.orglett.2c00472

  日期：2022.3.18

  A visible-light-induced method for the construction of heterocyclic scaffolds such as pyrido[1,2-a]indoles and indolizines via sulfonyl radical-triggered relay cyclization without employing any external photocatalyst has been developed. Preliminary mechanistic investigation indicated that indole and pyrrole derivatives could serve as pre-photocatalysts to promote the sulfonylation/cyclization, thereby

  已经开发了一种可见光诱导的方法，用于在不使用任何外部光催化剂的情况下通过磺酰基自由基触发的中继环化构建吡啶并[1,2 - a ]吲哚和中氮茚等杂环支架。初步机理研究表明，吲哚和吡咯衍生物可以作为预光催化剂促进磺酰化/环化，从而为合成有价值的磺酰化杂环提供了一种简便的方法。
• Photocatalytic Intramolecular [2 + 2] Cycloaddition of Indole Derivatives via Energy Transfer: A Method for Late-Stage Skeletal Transformation
  作者：Zhijie Zhang、Dong Yi、Min Zhang、Jun Wei、Ji Lu、Lin Yang、Jun Wang、Na Hao、Xianchao Pan、Shiqi Zhang、Siping Wei、Qiang Fu

  DOI：10.1021/acscatal.0c01841

  日期：2020.9.4

  cycloaddition of indole derivatives tethered with olefins at the N1 position has been considered thermodynamically unfeasible due to the high triplet excited-state energies. We describe visible light-promoted [2 + 2] cycloaddition with concomitant dearomatization of indole derivatives tethered with olefins at the N1 position via the energy transfer process, providing cyclobutane-fused polycyclic indoline derivatives

  由于高三重态激发态能量，在N1位置与烯烃拴在一起的吲哚衍生物的可见光促进脱芳香性[2 + 2]环加成反应在热力学上不可行。我们描述了可见光促进的[2 + 2]环加成反应，以及通过能量转移过程在N1位置与烯烃拴在一起的吲哚衍生物的脱芳香化，同时提供了可用于药物设计和发现的环丁烷稠合多环吲哚啉衍生物。这些环丁烷稠合的基于二氢吲哚的多环化合物以高收率和良好的非对映选择性（> 99：1）获得。反应成功的关键是在氮之间形成氢键-链烯基吲哚和溶剂，能够降低吲哚衍生物的三重态能量，从而大大提高了方案的效率。含吲哚生物活性分子的后期骨骼多样化证明了该方法的适用性，这为快速骨架重塑提供了强有力的策略。DFT计算用于深入了解反应途径。
• 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.
• NOUVEAUX DERIVES INDOLIQUES, LEURS PROCEDES DE PREPARATION ET LEURS UTILISATIONS NOTAMMENT EN TANT QU'ANTIBACTERIENS
  申请人：Université Joseph Fourier

  公开号：EP2121601B1

  公开（公告）日：2016-06-15