1-(1H-indol-3-yl)but-3-en-1-ol | 148587-88-6

• 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
• 英文名称: 1-(1H-indol-3-yl)but-3-en-1-ol
• 英文别名: 1-(3-indolyl)but-3-en-1-ol
• CAS: 148587-88-6
• 化学式: C₁₂H₁₃NO
• 分子量: 187.241
• InChiKey: HPJWFIQJEZTRNM-UHFFFAOYSA-N

物化性质

• 沸点：
  377.0±27.0 °C(Predicted)
• 密度：
  1.162±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  36
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(1H-indol-3-yl)but-3-en-1-ol 在 三氟乙酸 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以95%的产率得到1-(β-Indolyl)buta-1,3-diene
  参考文献：
  名称：

  Sheu, Jyh-Horng; Chen, Yua-Kuang; Chung, Huey-Fen, Journal of the Chemical Society. Perkin transactions I, 1998, # 12, p. 1959 - 1965

  摘要：

  DOI：
• 作为产物：
  描述：

  3-吲哚甲醛 、 3-溴丙烯 在 氢化镓 、 1-丁基-3-甲基咪唑溴盐 作用下， 反应 12.0h， 以72%的产率得到1-(1H-indol-3-yl)but-3-en-1-ol
  参考文献：
  名称：

  [bmim][Br] as a Solvent and Activator for the Ga-Mediated Barbier Allylation: Direct Formation of anN-Heterocyclic Carbene from Ga Metal

  摘要：

  The room-temperature ionic liquid (RTIL) [bmim][Br] has been found to be an excellent green and inexpensive medium for the Ga-mediated allylation of aromatic and aliphatic aldehydes and ketones. The RTIL activated the metal via formation of a Ga-N-heterocyclic carbene complex that assisted in the completion of the reaction at ambient temperature with only 0.5 equiv of Ga and 1.2 equiv of allyl bromide with respect to the carbonyl substrates. The present protocol required a much shorter time than those reported in the literature using other metals and solvents and proceeded with good yields and excellent selectivity.

  DOI：

  10.1021/jo3020775

文献信息

• Lewis Acid Catalyzed Intramolecular Direct Ene Reaction of Indoles
  作者：Bo Han、You-Cai Xiao、Yuan Yao、Ying-Chun Chen

  DOI：10.1002/anie.201005296

  日期：2010.12.27

  How to fuse heterocycles: The direct enamine–imine isomerization of indoles and subsequent intramolecular imino‐ene has been observed under Lewis acid catalysis. This unique reaction occurred for indoles that contain a tethered olefin functionality, and led to fused indoline heterocycles with excellent diastereocontrol (see scheme).

  如何融合杂环：在路易斯酸催化下已观察到吲哚和随后的分子内亚胺烯的直接烯胺-亚胺异构化。对于包含链状烯烃官能团的吲哚，会发生这种独特的反应，并导致稠合的二氢吲哚杂环具有出色的非对映异构控制作用（请参见方案）。
• Yamada, Fumio; Fukui, Yoshikazu; Shinmyo, Daisuke, Heterocycles, 1993, vol. 35, # 1, p. 99 - 104
  作者：Yamada, Fumio、Fukui, Yoshikazu、Shinmyo, Daisuke、Somei, Masanori

  DOI：——

  日期：——
• Synthesis of Yuehchukene Analogues, Murrapanine and Normurrapanine Utylizing Thermal Reaction of b-(1-Hydroxybutenyl)indoles under Neutral Reaction Conditions
  作者：Jyh-Horng Sheu、Yua-Kuang Chen、Huey-Fen Chung、Ping-Jyun Sung、Song-Fong Lin

  DOI：10.3987/com-96-7507

  日期：——

  beta-(1-Hydroxybutenyl)indoles, which were prepared in high yields from indole-3-carboxaldehyde, could be converted into yuehchukene analogues(8a, b) murrapanine (9a) and normurrapanine (9b) in one step under thermal-induced reaction conditions in neutral solution of ethylene glycol and water. beta-(1-Hydroxybutenyl)indoles are supposed to be dehydrated to 1-(beta-indolyl)-1,3-butadienes which react further to yuehchukene analogues via a Diels-Alder pathway. Murrapanine and normurrapanine showed a cytotoxicity toward KB cells.
• Allylindation of 1H-indole-3-carboxaldehyde in the presence of azoles—revisited
  作者：Giancarlo Cravotto、Giovanni B. Giovenzana、Angelo Maspero、Tullio Pilati、Andrea Penoni、Giovanni Palmisano

  DOI：10.1016/j.tetlet.2006.06.124

  日期：2006.9

  The allylindation of 1H-indole-3-carboxaldehyde in the presence of azoles (e.g., pyrazoles and imidazole) under aqueous Barbier-like conditions was reinvestigated and improved. Some of the results were at variance with a previous report (Tetrahedron Lett. 2003, 44, 2101). (c) 2006 Elsevier Ltd. All rights reserved.
• [bmim][Br] as a Solvent and Activator for the Ga-Mediated Barbier Allylation: Direct Formation of an<i>N</i>-Heterocyclic Carbene from Ga Metal
  作者：Dibakar Goswami、Angshuman Chattopadhyay、Anubha Sharma、Subrata Chattopadhyay

  DOI：10.1021/jo3020775

  日期：2012.12.21

  The room-temperature ionic liquid (RTIL) [bmim][Br] has been found to be an excellent green and inexpensive medium for the Ga-mediated allylation of aromatic and aliphatic aldehydes and ketones. The RTIL activated the metal via formation of a Ga-N-heterocyclic carbene complex that assisted in the completion of the reaction at ambient temperature with only 0.5 equiv of Ga and 1.2 equiv of allyl bromide with respect to the carbonyl substrates. The present protocol required a much shorter time than those reported in the literature using other metals and solvents and proceeded with good yields and excellent selectivity.