4-methyl-1,4-dihydrocyclopenta[b]indol-3(2H)-one | 16244-16-9

• 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: 4-methyl-1,4-dihydrocyclopenta[b]indol-3(2H)-one
• 英文别名: 1,4-dihydro-4-methyl-cyclopent[b]indol-3(2H)-one；4-methyl-1,2-dihydrocyclopenta[b]indol-3-one
• CAS: 16244-16-9
• 化学式: C₁₂H₁₁NO
• 分子量: 185.225
• InChiKey: JHRAQVUUGFXPMG-UHFFFAOYSA-N

物化性质

• 熔点：
  135.1-136.1 °C
• 沸点：
  362.0±11.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  4-methyl-1,4-dihydrocyclopenta[b]indol-3(2H)-one 在 titanium(IV) isopropylate 、 sodium hydroxide 、 disodium hydrogenphosphate 、 三氯化铝 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 生成 4-Methyl-3-(2-phenylethylimino)-1,2-dihydrocyclopenta[b]indol-7-ol
  参考文献：
  名称：

  Imino 1,2,3,4-tetrahydrocyclopent[b]indole carbamates as dual inhibitors of acetylcholinesterase and monoamine oxidase

  摘要：

  A series of imino 1,2,3,4-tetrahydrocyclopent[b]indole carbamates was prepared and evaluated as dual acetylcholinesterase (AChE) and monoamine oxidase (MAO) inhibitors. Halogen substitution ortho to the carbamate functionality in the eight position resulted in a significant increase in binding affinity for both AChE and MAO-A.

  DOI：

  10.1016/0960-894x(96)00072-8
• 作为产物：
  描述：

  3-吲哚丙酸 在 potassium hydroxide 作用下， 以 丙酮 、 甲苯 为溶剂， 反应 22.0h， 生成 4-methyl-1,4-dihydrocyclopenta[b]indol-3(2H)-one
  参考文献：
  名称：

  Design, synthesis and antiproliferative activity of indole analogues of indanocine

  摘要：

  报告了一系列新的吲哚类化合物的设计与合成，并展示了它们在NCI癌症细胞系中的抗增殖活性。因达诺辛对多种癌症细胞系表现出强效活性（平均GI50 < 20 nM），包括耐药癌细胞系，并且还抑制了转移性癌细胞的迁移。所描述的多个吲哚类化合物展现出与因达诺辛相似的活性特征，在多种癌症细胞系中表现出强效的抗增殖活性，为进一步开发提供了新的线索。

  DOI：

  10.1039/c3md00200d

文献信息

• Substituted 1,2,3,4-tetrahydrocyclopent[b]indoles,
  申请人：Hoechst-Roussel Pharmaceuticals Incorporated

  公开号：US05192789A1

  公开（公告）日：1993-03-09

  There are disclosed various compounds of the formula below, ##STR1## where n, X and R.sub.1 through R.sub.4 are as defined in the specification, which are useful for alleviating various memory dysfunctions characterized by a cholinergic deficit such as Alzheimer's disease. Compounds of this invention also inhibit monoamine oxidase and/or act at central .alpha..sub.2 -adrenergic receptors, and hence are useful as antidepressants.

  下面的公式揭示了各种化合物，##STR1## 其中n、X和R.sub.1到R.sub.4如规范中定义的那样，这些化合物对于缓解由胆碱缺乏引起的各种记忆功能障碍（如阿尔茨海默病）是有用的。本发明的化合物还抑制单胺氧化酶和/或作用于中枢α2-肾上腺素受体，因此可用作抗抑郁药。
• Synthesis of Cyclopenta[ <i>b</i> ]indoles via a Formal [3+2] Cyclization of <i>N</i> ‐Sulfonyl‐1,2,3‐triazoles and Indoles
  作者：Shengguo Duan、Wan Zhang、Yuntong Hu、Ze‐Feng Xu、Chuan‐Ying Li

  DOI：10.1002/adsc.202000624

  日期：2020.9.8

  Annulation of benzoxy‐tethered N‐sulfonyl‐1,2,3‐triazoles and indoles has been developed in this paper, providing an efficient and convenient access to valuable cyclopenta[b]indoles in moderate to good yields. α,β‐Unsaturated imine, which generated in situ from denitrogenation and 1,2‐OBz migration of triazole, provided three carbons for the formal [3+2] cyclization reaction for the first time.

  本文开发了苯氧基束缚的N-磺酰基-1，2，3-三唑和吲哚的环化反应，可有效，方便地获得中度到良好收率的有价值的环戊[ b ]吲哚。由三唑的脱氮和1,2-OBz迁移原位产生的α，β-不饱和亚胺，首次为正式的[3 + 2]环化反应提供了三个碳。
• Intramolecular Friedel–Crafts Acylation Reaction Promoted by 1,1,1,3,3,3-Hexafluoro-2-propanol
  作者：Hashim F. Motiwala、Rakesh H. Vekariya、Jeffrey Aubé

  DOI：10.1021/acs.orglett.5b02851

  日期：2015.11.6

  Simple dissolution of an arylalkyl acid chloride in 1,1,1,3,3,3-hexafluoro-2-propanol promotes an intramolecular Friedel–Crafts acylation without additional catalysts or reagents. This reaction is operationally trivial in both execution and product isolation (only requiring concentration followed by purification) and accommodates a broad range of substrates. Preliminary studies that bear upon potential

  芳基烷基酰氯在1,1,1,3,3,3-六氟-2-丙醇中的简单溶解可促进分子内Friedel-Crafts酰化反应，而无需其他催化剂或试剂。该反应在操作和产物分离上都操作上很简单（只需要浓缩后再纯化），并适用于各种各样的底物。据报道涉及潜在反应机理的初步研究。
• Synthesis of Cycloalk[<i>b</i>]indole Bearing Spiropiperidine Derivatives
  作者：Cevher Gündoğdu Hızlıateş、Sibel Gülle、Yavuz Ergün

  DOI：10.1002/jhet.2395

  日期：2016.1

  The novel heterocyclic compounds that have cycloalk[b]indole moiety bearing spiropiperidinone and spiropiperidinedione (3a, 3b, 3c, 5a, 5b, 8a, 8b, and 10a) were synthesized for the first time. The synthesis of spiropiperidinone and spiropiperidinedione structures was performed by a new method. These compounds are similar to sedative and hypnotic drugs such as methyprylon, glutethimide, and thalidomide

  首次合成了具有带有螺哌啶酮和螺哌啶二酮（3a，3b，3c，5a，5b，8a，8b和10a）的环烷基[ b ]吲哚部分的新型杂环化合物。螺哌啶酮和螺哌啶二酮结构的合成采用新方法进行。这些化合物类似于镇静药和催眠药，例如甲氧乙丙啶，谷氨酰胺和沙利度胺。
• Recent advances in the synthesis of analogues of phytohormones strigolactones with ring-closing metathesis as a key step
  作者：Chiara Lombardi、Emma Artuso、Eleonora Grandi、Marco Lolli、Francesca Spirakys、Emanuele Priola、Cristina Prandi

  DOI：10.1039/c7ob01917c

  日期：——

  Structural analogues of natural strigolactones in which the butenolide D-ring has been replaced with γ-lactam. The key step was an RCM on suitably substituted amides.

  将天然分枝酮的结构类似物中的丁烯内酯D环替换为γ-内酰胺。关键步骤是在适当取代的酰胺上进行环状烯烃交叉二聚反应。