2-chloro-4'-cyano-3',4',5',6'-tetrahydro-2'H-[3,4']-bipyridinyl-1'-carboxylic acid tert-butyl ester | 1315335-16-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 2-chloro-4'-cyano-3',4',5',6'-tetrahydro-2'H-[3,4']-bipyridinyl-1'-carboxylic acid tert-butyl ester
• 英文别名: 1-Piperidinecarboxylic acid, 4-(2-chloro-3-pyridinyl)-4-cyano-, 1,1-dimethylethyl ester；tert-butyl 4-(2-chloropyridin-3-yl)-4-cyanopiperidine-1-carboxylate
• CAS: 1315335-16-0
• 化学式: C₁₆H₂₀ClN₃O₂
• 分子量: 321.807
• InChiKey: WEKDZLAYEVGPGH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  66.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-chloro-4'-cyano-3',4',5',6'-tetrahydro-2'H-[3,4']-bipyridinyl-1'-carboxylic acid tert-butyl ester 在 双氧水 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 以95%的产率得到N-boc-4-(2-氯吡啶-3-基)哌啶-4-甲酰胺
  参考文献：
  名称：

  A spirocyclic oxindole analogue: Synthesis and antitumor activities

  摘要：

  A new synthesis of spirocyclic oxindole analogue spiro[piperidine-4,3'-pyrrolo[2,3-b]pyridin]-2'(1'H)-one 1 is described. The key steps involve dialkylation of arylacetonitrile and cyclization of the azaoxindole ring by an intramolecular Buchwald Hartwig amidation of carboxylic amide and aryl chloride. A small library was obtained by reductive amination of 1 with various aldehydes and was screened against human lung cancer cell A549, human liver cancer cell BEL7402, and human colon cancer cell HCT-8. The results show that most of the library compounds 2 have some inhibitory activities. 2-(Trifluoromethoxy) benzylic substituted spirocyclic azaoxindole 2e was identified as a nanomolar inhibitor against human lung cancer cell A-549 (IC50 = 50 nmol/L). (C) 2011 Da Wei Teng. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

  DOI：

  10.1016/j.cclet.2011.01.042
• 作为产物：
  描述：

  2-氯-3-吡啶甲醇 在 磺酰氯 、 sodium hydride 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.33h， 生成 2-chloro-4'-cyano-3',4',5',6'-tetrahydro-2'H-[3,4']-bipyridinyl-1'-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  A spirocyclic oxindole analogue: Synthesis and antitumor activities

  摘要：

  A new synthesis of spirocyclic oxindole analogue spiro[piperidine-4,3'-pyrrolo[2,3-b]pyridin]-2'(1'H)-one 1 is described. The key steps involve dialkylation of arylacetonitrile and cyclization of the azaoxindole ring by an intramolecular Buchwald Hartwig amidation of carboxylic amide and aryl chloride. A small library was obtained by reductive amination of 1 with various aldehydes and was screened against human lung cancer cell A549, human liver cancer cell BEL7402, and human colon cancer cell HCT-8. The results show that most of the library compounds 2 have some inhibitory activities. 2-(Trifluoromethoxy) benzylic substituted spirocyclic azaoxindole 2e was identified as a nanomolar inhibitor against human lung cancer cell A-549 (IC50 = 50 nmol/L). (C) 2011 Da Wei Teng. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

  DOI：

  10.1016/j.cclet.2011.01.042

文献信息

• [EN] SPIROPIPERIDINE DERIVATIVES FOR CONTROLLING PESTS<br/>[FR] DÉRIVÉS DE SPIROPIPÉRIDINE POUR LUTTER CONTRE LES NUISIBLES
  申请人：SYNGENTA PARTICIPATIONS AG

  公开号：WO2005061500A1

  公开（公告）日：2005-07-07

  The use of a compound of Formula (I), Y is a single bond, C=O, C=S or S(O)m where m is 0, 1 or 2; the ring represented by T is a 5 or 6 membered heteroaromatic and R1, R2, R3, R8 and Ra are specified organic groups and p is 0, 1, 2, 3, 4, 5 or 6; p+q is 1, 2, 3, 4, 5 or 6; or salts or N-oxides thereof or compositions containing them in controlling insects, acarines, nematodes or molluscs; novel compounds are also provided.

  使用Formula（I）中的化合物，其中Y是单键，C=O，C=S或S（O）m，其中m为0、1或2；T表示的环是5或6个成员的杂芳族，R1、R2、R3、R8和Ra是指定的有机基团，p为0、1、2、3、4、5或6；p+q为1、2、3、4、5或6；或其盐或N-氧化物或含有它们的组合物在控制昆虫、螨虫、线虫或软体动物方面；还提供了新化合物。
• Spiropiperidine derivatives for controlling pests
  申请人：Cassayre Jerome

  公开号：US20070135408A1

  公开（公告）日：2007-06-14

  The use of a compound of Formula (I), Y is a single bond, C═O, C═S or S(O)m where m is 0, 1 or 2; the ring represented by T is a 5 or 6 membered heteroaromatic and R 1 , R 2 , R 3 , R 8 and Ra are specified organic groups and p is 0, 1, 2, 3, 4, 5 or 6; p+q is 1, 2, 3, 4, 5 or 6; or salts or N-oxides thereof or compositions containing them in controlling insects, acarines, nematodes or molluscs; novel compounds are also provided.

  使用式（I）化合物，其中Y为单键，C═O，C═S或S（O）m，其中m为0、1或2；所表示的环T为5或6成员的杂环芳香族，并且R1、R2、R3、R8和Ra是指定的有机基团，p为0、1、2、3、4、5或6；p+q为1、2、3、4、5或6；或其盐或N-氧化物或含有它们的组合物，在控制昆虫、螨、线虫或软体动物方面提供了新的化合物。
• SPIROPIPERIDINE DERIVATIVES FOR CONTROLLING PESTS
  申请人：Syngenta Participations AG

  公开号：EP1694677B1

  公开（公告）日：2009-12-02
• US7960401B2
  申请人：——

  公开号：US7960401B2

  公开（公告）日：2011-06-14
• A spirocyclic oxindole analogue: Synthesis and antitumor activities
  作者：Hui Hong、Long Jiang Huang、Da Wei Teng

  DOI：10.1016/j.cclet.2011.01.042

  日期：2011.9

  A new synthesis of spirocyclic oxindole analogue spiro[piperidine-4,3'-pyrrolo[2,3-b]pyridin]-2'(1'H)-one 1 is described. The key steps involve dialkylation of arylacetonitrile and cyclization of the azaoxindole ring by an intramolecular Buchwald Hartwig amidation of carboxylic amide and aryl chloride. A small library was obtained by reductive amination of 1 with various aldehydes and was screened against human lung cancer cell A549, human liver cancer cell BEL7402, and human colon cancer cell HCT-8. The results show that most of the library compounds 2 have some inhibitory activities. 2-(Trifluoromethoxy) benzylic substituted spirocyclic azaoxindole 2e was identified as a nanomolar inhibitor against human lung cancer cell A-549 (IC50 = 50 nmol/L). (C) 2011 Da Wei Teng. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.