methyl 7-chloro-1H-indole-2-carboxylate | 940960-50-9

• 物质功能分类: 化学试剂 - 有机试剂 - 酯类
• 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 7-chloro-1H-indole-2-carboxylate
• CAS: 940960-50-9
• 化学式: C₁₀H₈ClNO₂
• 分子量: 209.632
• InChiKey: RCRPSJJKJAAOLE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  42.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  methyl 7-chloro-1H-indole-2-carboxylate 在 氢氧化钾 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 生成 (7-Chloro-1-methylindol-2-yl)methanol
  参考文献：
  名称：

  Enantioselective Organocatalytic Intramolecular Ring-Closing Friedel−Crafts-Type Alkylation of Indoles

  摘要：

  An enantioselective organocatalytic intramolecular ring-closing Friedel-Crafts-type alkylation of indolyl alpha,beta-unsaturated aldehydes has been developed. This powerful new strategy allows enantioselective access to THPIs and THBCs in a straightforward and atom-economical manner.

  DOI：

  10.1021/ol0703130
• 作为产物：
  描述：

  3-氯苯甲醛 在 Rh₂(pbf)4 sodium methylate 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 20.0h， 生成 methyl 7-chloro-1H-indole-2-carboxylate
  参考文献：
  名称：

  Intramolecular C−H Amination Reactions:  Exploitation of the Rh₂(II)-Catalyzed Decomposition of Azidoacrylates

  摘要：

  Rhodium(II) perfluorobutyrate-mediated decomposition of vinyl azides provides a new, mild entry into Rh-2(II) nitrenoid chemistry. This methodology allows rapid access to a variety of complex, functionalized N-heterocycles in two steps from commercially available starting materials.

  DOI：

  10.1021/ja072219k

文献信息

• [EN] AZA-OXO-INDOLES FOR THE TREATMENT AND PROPHYLAXIS OF RESPIRATORY SYNCYTIAL VIRUS INFECTION<br/>[FR] AZA-OXO-INDOLES POUR LE TRAITEMENT ET LA PROPHYLAXIE DE L'INFECTION À VIRUS RESPIRATOIRE SYNCYTIAL
  申请人：HOFFMANN LA ROCHE

  公开号：WO2014184163A1

  公开（公告）日：2014-11-20

  The invention provides compounds having the general formula: wherein R1, R2, R3, R4, R5, R6, W1, W2, W3, A and X are as described herein, compositions including the compounds and methods of using the compounds.

  这项发明提供了具有以下一般式的化合物：其中R1、R2、R3、R4、R5、R6、W1、W2、W3、A和X如本文所述，包括这些化合物的组合物以及使用这些化合物的方法。
• NOVEL AZA-OXO-INDOLES FOR THE TREATMENT AND PROPHYLAXIS OF RESPIRATORY SYNCYTIAL VIRUS INFECTION
  申请人：Hoffmann-La Roche Inc.

  公开号：US20160068531A1

  公开（公告）日：2016-03-10

  The invention provides novel compounds having the general formula: wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , W 1 , W 2 , W 3 , A and X are as described herein, compositions including the compounds and methods of using the compounds.

  本发明提供了一种具有一般式的新化合物：其中R1、R2、R3、R4、R5、R6、W1、W2、W3、A和X如本文所述，包括该化合物的组合物和使用该化合物的方法。
• Aza-oxo-indoles for the treatment and prophylaxis of respiratory syncytial virus infection
  申请人：Hoffmann-La Roche Inc.

  公开号：US10189838B2

  公开（公告）日：2019-01-29

  The invention provides novel compounds having the general formula: wherein R1, R2, R3, R4, R5, R6, W1, W2, W3, A and X are as described herein, compositions including the compounds and methods of using the compounds for the treatment and prophylaxis of respiratory syncytial virus infection.

  本发明提供了具有通式的新型化合物： 其中 R1、R2、R3、R4、R5、R6、W1、W2、W3、A 和 X 如本文所述；包括这些化合物的组合物；以及使用这些化合物治疗和预防呼吸道合胞病毒感染的方法。
• Extending the versatility of the Hemetsberger–Knittel indole synthesis through microwave and flow chemistry
  作者：Nadeesha Ranasinghe、Graham B. Jones

  DOI：10.1016/j.bmcl.2013.01.066

  日期：2013.3

  Microwave, flow and combination methodologies have been applied to the synthesis of a number of substituted indoles. Based on the Hemetsberger-Knittel (HK) process, modifications allow formation of products rapidly and in high yield. Adapting the methodology allows formation of 2-unsubstituted indoles and derivatives, and a route to analogs of the antitumor agent PLX-4032 is demonstrated. The utility of the HK substrates is further demonstrated through bioconjugation and subsequent ring closure and via Huisgen type [3+2] cycloaddition chemistry, allowing formation of peptide adducts which can be subsequently labeled with fluorine tags. (C) 2013 Elsevier Ltd. All rights reserved.
• Discovery of indole inhibitors of chemokine receptor 9 (CCR9)
  作者：Bhaumik A. Pandya、Christian Baber、Audrey Chan、Brian Chamberlain、Haoqun Chandonnet、Jennifer Goss、Timothy Hopper、Blaise Lippa、Katherine Poutsiaka、Jan Romero、Sabrina Stucka、Mustafa Varoglu、Jing Zhang、Xin Zhang

  DOI：10.1016/j.bmcl.2016.05.043

  日期：2016.7

  Irritable bowel diseases (IBD) such as Crohn's disease (CD) and ulcerative colitis (UC) are serious chronic diseases affecting millions of patients worldwide. Studies of human chemokine biology has suggested C-C chemokine receptor 9 (CCR9) may be a key mediator of pro-inflammatory signaling. Discovery of agents that inhibit CCR9 may lead to new therapies for CD and UC patients. Herein we describe the evolution of a high content screening hit (1) into potent inhibitors of CCR9, such as azaindole 12. (C) 2016 Elsevier Ltd. All rights reserved.