methyl 1-methyl-2,3-dihydro-1H-indole-3-carboxylate | 39891-72-0

• 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: methyl 1-methyl-2,3-dihydro-1H-indole-3-carboxylate
• 英文别名: 1-methyl-2,3-dihydro-indole-3-carboxylic acid methyl ester；Methyl 1-methyl-2,3-dihydroindole-3-carboxylate
• CAS: 39891-72-0
• 化学式: C₁₁H₁₃NO₂
• 分子量: 191.23
• InChiKey: ZQQLBNORLKPGQO-UHFFFAOYSA-N

物化性质

• 沸点：
  265.8±40.0 °C(Predicted)
• 密度：
  1.143±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  methyl 2-[tert-butyl-[1-[diethoxy(oxido)phosphaniumyl]-2,2-dimethylpropyl]amino]oxy-3-(N-methylanilino)propanoate 以 叔丁醇 为溶剂， 反应 12.0h， 以75%的产率得到methyl 1-methyl-2,3-dihydro-1H-indole-3-carboxylate
  参考文献：
  名称：

  Alkoxyamine-Mediated Radical Synthesis of Indolinones and Indolines

  摘要：

  [GRAPHICS]Thermolysis of alpha-alkoxyamino propionanilides produces indolinones, whereas thermal reaction of N-allylaniline derivatives with various Tordo-type alkoxyamines results in formation of indolines in the radical regime.

  DOI：

  10.1021/ol0358049

文献信息

• NOVEL COMPOUNDS
  申请人：Gottschling Dirk

  公开号：US20110195954A1

  公开（公告）日：2011-08-11

  The present invention relates to new CGRP-antagonists of general formula I wherein U, V, X, Y, R 1 , R 2 , R 3 and R 4 are defined as mentioned in the description, the tautomers thereof, the isomers thereof, the diastereomers thereof, the enantiomers thereof, the hydrates thereof, the mixtures thereof and the salts thereof as well as the hydrates of the salts, particularly the physiologically acceptable salts thereof with inorganic or organic acids or bases, medicaments containing these compounds, the use thereof and processes for the preparation thereof.

  本发明涉及一般式I的新CGRP拮抗剂，其中U、V、X、Y、R1、R2、R3和R4如描述中所述定义，其互变异构体、异构体、顺反异构体、对映异构体、水合物、混合物及其盐，以及其盐的水合物，特别是与无机或有机酸或碱形成的生理上可接受的盐，包含这些化合物的药物、其用途以及其制备方法。
• Electroreductive Intermolecular Coupling of 3-Methoxycarbonylindoles with Ketones
  作者：Naoki Kise、Akinori Sueyoshi、Shin-ichirou Takeuchi、Toshihiko Sakurai

  DOI：10.1021/ol4010799

  日期：2013.6.7

  The electroreductive coupling of 1-alkoxycarbonyl-3-methoxycarbonylindoles with aromatic ketones in the presence of chlorotrimethylsilane gave cis-adducts stereoselectively. The cis-adducts were readily transformed to trans-adducts by treatment with catalyst DBU. On the other hand, the electroreductive coupling of 1-methyl-3-methoxycarbonylindole with aliphatic ketones in isopropanol afforded trans-adducts

  在氯代三甲基硅烷存在下，1-烷氧基羰基-3-甲氧基羰基吲哚与芳族酮的电还原偶联立体选择性地产生了顺式加合物。所述顺式-adducts被容易地转化为反式通过用催化剂DBU治疗-adducts。另一方面，在异丙醇中1-甲基-3-甲氧基羰基吲哚与脂肪族酮的电还原偶联仅提供了反式加合物。加合物是合成2-取代的3-甲氧基羰基吲哚和二氢吲哚的前体。
• Electroreductive Intramolecular Coupling of 1-Indolealkanones
  作者：Naoki Kise、Toshiyuki Mano、Toshihiko Sakurai

  DOI：10.1021/ol801876k

  日期：2008.10.16

  The electroreduction of 1-indolealkanones in isopropanol gave five-, six-, and seven-membered trans-cyclized products stereospecifically. On the other hand, the electroreduction of 3-methoxycarbonyl-1-indolealkanones afforded mixtures of two diastereomers of the corresponding trans- and cis-cyclized products. The DFT calculations for the radical anions support that the reductive couplings of 1-indolealkanones

  1-吲哚链烷酮在异丙醇中的电还原立体定向生成五元，六元和七元反式环化产物。另一方面，3-甲氧基羰基-1-吲哚链烷酮的电还原得到相应反式和顺式环化产物的两种非对映异构体的混合物。自由基阴离子的DFT计算支持1-吲哚链烷酮和3-甲氧基羰基-1-吲哚链烷酮的还原偶联通过不同的反应机理进行。
• Synthesis of Indole-3-carboxylic Acid Derivatives by Pd(0)-Catalyzed Intramolecular α-Arylation of β-(2-Iodoanilino) Esters
  作者：Daniel Solé、Olga Serrano

  DOI：10.1021/jo800034m

  日期：2008.3.1

  beta-(2-Iodoanilino) esters undergo intramolecular alpha-arylation in the presence of Pd(PPh3)(4) and potassium phenoxide. The reaction is a useful methodology for the preparation of indole-3-carboxylic acid ester derivatives.
• Tamura, Yasumitsu; Ikeda, Hiroyuki; Mukai, Chisato, Chemical and pharmaceutical bulletin, 1980, vol. 28, # 11, p. 3430 - 3433
  作者：Tamura, Yasumitsu、Ikeda, Hiroyuki、Mukai, Chisato、Bayomi, Said Mohamad M.、Ikeda, Masazumi

  DOI：——

  日期：——