N-cyclohexyl-4-oxo-4,5,6,7-tetrahydroindole | 23922-57-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯嗪
• 英文名称: N-cyclohexyl-4-oxo-4,5,6,7-tetrahydroindole
• 英文别名: 1-Cyclohexyl-4,5,6,7-tetrahydroindol-4-on；1-cyclohexyl-6,7-dihydro-5H-indol-4-one
• CAS: 23922-57-8
• 化学式: C₁₄H₁₉NO
• 分子量: 217.311
• InChiKey: GPWQGQVHPVZPIW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  22
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  6,7-二氢-4(5H)-苯并呋喃酮 、 环己胺 以 乙醇 、 水 为溶剂， 反应 12.0h， 以36%的产率得到N-cyclohexyl-4-oxo-4,5,6,7-tetrahydroindole
  参考文献：
  名称：

  Formation of N-substituted 4- and 7-oxo-4,5,6,7-tetrahydroindoles revisited: a mechanistic interpretation and conversion into 4- and 7-oxoindoles

  摘要：

  An efficient method for the preparation of 4-oxo-4,5,6,7-tetrahydroindoles was successfully applied to the synthesis of N-substituted 7-oxo-4,5,6,7-tetrahydroindoles for the first time. Both isomers where converted into their corresponding 4- and 7-oxoindoles in good yields utilizing a novel aromatization protocol. Based on the impurity profile obtained, however, different mechanisms for the formation of the 4- and 7-oxo-4,5,6,7-tetrahydroindole derivatives are discussed. In addition, the reaction sequences appear to be stereospecific allowing for the direct introduction of a chiral center a to the nitrogen and preparation of enantiomerically enriched products. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.05.090

文献信息

• 1,3-Cyclohexanedione derivatives
  申请人：Kuraray Co., Ltd.

  公开号：US04336202A1

  公开（公告）日：1982-06-22

  Novel cyclohexanone derivatives of general formula: ##STR1## (wherein R.sup.1 is a hydrocarbon group of 1 to 15 carbon atoms) and new cyclohexanone derivatives of general formula: ##STR2## (wherein R.sup.1 and R.sup.2 each is a hydrocarbon group of 1 to 15 carbon atoms) are produced by an electrooxidative coupling of 1,3-cyclohexanedione with a vinyl ether of general formula: CH.sub.2 .dbd.CH-O-R.sup.1 (wherein R.sup.1 is as defined above) in the presence or absence of an alcohol of general formula: R.sup.2 OH (wherein R.sup.2 is as defined above). These new cyclohexanone derivatives can be easily converted to N-substituted or unsubstituted-4-oxo-4,5,6,7-tetrahydroindoles, which are of value as intermediates for the production of N-substituted or unsubstituted-4-hydroxyindoles and, thence, to pindolol and its analogs.

  通用公式的新环己酮衍生物：##STR1##（其中R.sup.1是1到15个碳原子的碳氢基团）和通用公式的新环己酮衍生物：##STR2##（其中R.sup.1和R.sup.2分别是1到15个碳原子的碳氢基团）通过1,3-环己二酮与通用公式的乙烯醚进行电氧化耦合制备：CH.sub.2 .dbd.CH-O-R.sup.1（其中R.sup.1如上定义）在存在或不存在通用公式的醇：R.sup.2 OH（其中R.sup.2如上定义）的情况下。这些新环己酮衍生物可以轻松转化为N-取代或未取代的4-氧代-4,5,6,7-四氢吲哚，这对于生产N-取代或未取代的4-羟基吲哚及其衍生物，进而得到贝特诺洛尔及其类似物具有价值。
• Microwave-assisted synthesis of tetrahydroindoles
  作者：Leonarda Piras、Chiara Ghiron、Giacomo Minetto、Maurizio Taddei

  DOI：10.1016/j.tetlet.2007.11.114

  日期：2008.1

  An efficient synthesis of tetrahydroindoles with different substituents in position I is described. Microwave-assisted aminolysis of 4-oxo-4,5,6,7-tetrahydrobenzofuran With different primary amines gives the corresponding tetrahydroindoles in few minutes. All attempts to use microwave dielectric heating to reduce the time required for preparation of 4-oxo-4,5,6,7-tetrahydrobenzofuran, starting from 1,3-cyclohexandione were on the other hand unsuccessful, demonstrating that in some cases, long time conventional heating may be superior to microwaves. (C) 2007 Elsevier Ltd. All rights reserved.
• US4336202A
  申请人：——

  公开号：US4336202A

  公开（公告）日：1982-06-22