1-(tert-butoxycarbonyl)-5-chloroindoline | 143262-12-8

• 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-(tert-butoxycarbonyl)-5-chloroindoline
• 英文别名: Tert-butyl 5-chloro-2,3-dihydroindole-1-carboxylate
• CAS: 143262-12-8
• 化学式: C₁₃H₁₆ClNO₂
• 分子量: 253.729
• InChiKey: IHXCTZFQPUKXJO-UHFFFAOYSA-N

物化性质

• 熔点：
  129-130 °C
• 沸点：
  350.3±41.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  二氧化碳 、 1-(tert-butoxycarbonyl)-5-chloroindoline 在 四甲基乙二胺 、 仲丁基锂 作用下， 以 四氢呋喃 为溶剂， 生成
  参考文献：
  名称：

  A novel series of potent and selective EP4 receptor ligands: Facile modulation of agonism and antagonism

  摘要：

  A novel series of EP4 ligands, based on a benzyl indoline scaffold, has been discovered. It was found that agonism and antagonism in this series can be easily modulated by minor modifications on the benzyl group. The pharmacokinetic, metabolic and pharmacological profiles of these compounds was explored. It was found that these compounds show good pharmacokinetics in rat and are efficacious in pre-clinical models of pain and inflammation. (c) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.10.106
• 作为产物：
  描述：

  5-氯吲哚 在 sodium cyanoborohydride 作用下， 以 乙醚 、 溶剂黄146 为溶剂， 生成 1-(tert-butoxycarbonyl)-5-chloroindoline
  参考文献：
  名称：

  Directed Lithiation of 1-(tert-Butoxycarbonyl)indolines. A Convenient Route to 7-Substituted Indolines

  摘要：

  1-(tert-Butoxycarbonyl)indolines were regioselectively lithiated at 7-position with s-BuLi-TMEDA in ether or TBF at -78-degrees-C. The lithiated species were reacted with a range of electrophiles to give 7-substituted indoline derivatives.

  DOI：

  10.3987/com-92-5993

文献信息

• Improved Substrate Scope in the Potassium Hexacyanoferrate(II)-Based Cyanation for the Synthesis of Benzonitriles and Their Heterocyclic Analogues
  作者：Jeffery Richardson、Simon P. Mutton

  DOI：10.1021/acs.joc.8b00515

  日期：2018.5.4

  The use of Pd(DPEPhos)Cl2 (P26) as a catalyst for the formation of benzonitriles and their heterocyclic analogues provides excellent complementarity to existing catalysts, allowing highly electron-deficient heterocyclic aryl halides to be efficiently converted to the corresponding nitriles using K4[Fe(CN)6]) as cyanide source. This catalyst significantly enhances the scope of this reaction to include

  使用Pd（DPEPhos）Cl 2（P26）作为形成苄腈及其杂环类似物的催化剂可提供与现有催化剂的出色互补性，从而使高度缺电子的杂环芳基卤化物可通过K 4有效地转化为相应的腈[Fe（CN）6]）作为氰化物源。该催化剂大大增加了反应的范围，使其包含许多与制药和农业化学应用高度相关的底物。重要的是，这种氰化方法不仅使用无毒的氰化物源，简单的半定量测试表明，与许多其他方法不同，反应混合物中或在各种潜在的后处理过程中均不存在游离氰化物，从而提高了该方法的安全性。从初始设置到产品隔离。最终，开发和测试了一系列方便的氰化试剂盒，使得该方法易于应用，并在我们的实验室中得到了更广泛的采用。
• Hydrogenation of Five-Membered Heteroaromatic Compounds Catalyzed by a Rhodium-Phosphine Complex
  作者：Ryoichi Kuwano、Koji Sato、Yoshihiko Ito

  DOI：10.1246/cl.2000.428

  日期：2000.4

  The rhodium complex generated in situ from Rh(acac)(cod) and 2 equivalents of triphenylphosphine is an effective catalyst for hydrogenation of various five-membered heteroaromatic compounds.

  由 Rh(acac)(cod) 和 2 当量的三苯基膦原位生成的铑配合物是各种五元杂芳族化合物加氢的有效催化剂。
• An <i>o</i>-Iminothioquinone:  Its Cycloaddition To Produce an Indologlycoside and Its Self-Dimerization To Form a Dithio-Diazocycloctane, the Structure Assignment of Which Is Based on the DFT Prediction of Its IR Spectrum
  作者：Vinh Diep、J. J. Dannenberg、Richard W. Franck

  DOI：10.1021/jo034800e

  日期：2003.10.1

  An unusual heterodiene, an indolothiono quinone, undergoes cycloaddition with a glycal to form an indole-N-glycoside. A novel dimer of the indolothionoquinone is assigned its structure on the basis of a match between its predicted and observed IR spectrum.
• Directed Lithiation of 1-(tert-Butoxycarbonyl)indolines. A Convenient Route to 7-Substituted Indolines
  作者：Masatomo Iwao、Tsukasa Kuraishi

  DOI：10.3987/com-92-5993

  日期：——

  1-(tert-Butoxycarbonyl)indolines were regioselectively lithiated at 7-position with s-BuLi-TMEDA in ether or TBF at -78-degrees-C. The lithiated species were reacted with a range of electrophiles to give 7-substituted indoline derivatives.
• A novel series of potent and selective EP4 receptor ligands: Facile modulation of agonism and antagonism
  作者：Michael J. Boyd、Carl Berthelette、Jean-François Chiasson、Patsy Clark、John Colucci、Danielle Denis、Yongxin Han、Jean-Francois Lévesque、Marie-Claude Mathieu、Rino Stocco、Alex Therien、Steve Rowland、Mark Wrona、Daigen Xu

  DOI：10.1016/j.bmcl.2010.10.106

  日期：2011.1

  A novel series of EP4 ligands, based on a benzyl indoline scaffold, has been discovered. It was found that agonism and antagonism in this series can be easily modulated by minor modifications on the benzyl group. The pharmacokinetic, metabolic and pharmacological profiles of these compounds was explored. It was found that these compounds show good pharmacokinetics in rat and are efficacious in pre-clinical models of pain and inflammation. (c) 2010 Elsevier Ltd. All rights reserved.