1-[trans-3-(4-chlorophenyl)allyl]-4-oxopiperidine | 637362-28-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-[trans-3-(4-chlorophenyl)allyl]-4-oxopiperidine
• 英文别名: 1-[(E)-3-(4-chloro-phenyl)-allyl]-piperidin-4-one；1-[(E)-3-(4-chlorophenyl)prop-2-enyl]piperidin-4-one
• CAS: 637362-28-8
• 化学式: C₁₄H₁₆ClNO
• 分子量: 249.74
• InChiKey: CROUWYIAKLVLNP-OWOJBTEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-[trans-3-(4-chlorophenyl)allyl]-4-oxopiperidine 在 potassium tert-butylate 、 三氟乙酸 作用下， 以 四氢呋喃 为溶剂， 生成 (E)-1'-(3-(4-chlorophenyl)allyl)-5-fluorospiro[indoline-3,4'-piperidine]
  参考文献：
  名称：

  Do spiroindolines have the potential to replace vesamicol as lead compound for the development of radioligands targeting the vesicular acetylcholine transporter?

  摘要：

  The vesicular acetylcholine transporter (VAChT) is an important target for in vivo imaging of neurodegenerative processes using positron emission tomography (PET). So far the development of VAChT PET radioligands is based on the single known lead compound vesamicol. In this study we investigated a recently published spiroindoline based compound class (Sluder et al., 2012), which was suggested to have potential in the development of VAChT ligands. Therefore, we synthesized a small series of N,N-substituted spiro[indoline-3,4'-piperidine] derivatives and determined their in vitro binding affinities toward the VAChT. In order to investigate the selectivity, the off-target binding toward sigma(1) and sigma(2) receptors was determined. The compounds possessed VAChT affinities with K-i values in the range of 39-376 nM. Binding affinities toward the sigma(1) and sigma(2) receptors are in a similar range indicating that the strong structural difference between the spiroindolines and vesamicol did not improve the selectivity. The observed potential to additionally bind to sigma receptors let us assume that the herein investigated spiroindolines are not suitable to replace vesamicol as lead compound for the development of VAChT ligands. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2017.03.028
• 作为产物：
  描述：

  4-哌啶酮缩乙二醇 在 盐酸 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 氯仿 、 水 为溶剂， 生成 1-[trans-3-(4-chlorophenyl)allyl]-4-oxopiperidine
  参考文献：
  名称：

  Do spiroindolines have the potential to replace vesamicol as lead compound for the development of radioligands targeting the vesicular acetylcholine transporter?

  摘要：

  The vesicular acetylcholine transporter (VAChT) is an important target for in vivo imaging of neurodegenerative processes using positron emission tomography (PET). So far the development of VAChT PET radioligands is based on the single known lead compound vesamicol. In this study we investigated a recently published spiroindoline based compound class (Sluder et al., 2012), which was suggested to have potential in the development of VAChT ligands. Therefore, we synthesized a small series of N,N-substituted spiro[indoline-3,4'-piperidine] derivatives and determined their in vitro binding affinities toward the VAChT. In order to investigate the selectivity, the off-target binding toward sigma(1) and sigma(2) receptors was determined. The compounds possessed VAChT affinities with K-i values in the range of 39-376 nM. Binding affinities toward the sigma(1) and sigma(2) receptors are in a similar range indicating that the strong structural difference between the spiroindolines and vesamicol did not improve the selectivity. The observed potential to additionally bind to sigma receptors let us assume that the herein investigated spiroindolines are not suitable to replace vesamicol as lead compound for the development of VAChT ligands. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2017.03.028

文献信息

• [EN] SPIROINDOLINEPIPERIDINE DERIVATIVES<br/>[FR] DERIVES DE SPIROINDOLINEPIPERIDINE
  申请人：SYNGENTA LTD

  公开号：WO2003106457A1

  公开（公告）日：2003-12-24

  Insecticidal, acaricidal, nematicidal or molluscicidal compounds of formula (I) wherein Y is a single bond, C=O, C=S or C=(O)q where q is 0, 1 or 2; and R1, R2, R3, R4, R8, R9 and R10 are as defined in the claims or salts or N-oxides thereof, processes for preparing them and compositions containing them.

  化学式（I）中的杀虫剂、杀螨剂、杀线虫剂或杀软体动物剂，其中Y是单键，C=O，C=S或C=(O)q，其中q为0、1或2；以及R1、R2、R3、R4、R8、R9和R10如索赔中所定义的化合物，其盐或N-氧化物，制备它们的过程以及含有它们的组合物。
• Spiroindolinepiperidine derivatives
  申请人：Hughes David John

  公开号：US20060106045A1

  公开（公告）日：2006-05-18

  Insecticidal, acaricidal, nematicidal or molluscicidal compounds of formula (I) wherein Y is a single bond, C═O, C═S or C═(O) q where q is 0, 1 or 2; and R 1 , R 2 , R 3 , R 4 , R 8 , R 9 and R 10 are as defined in the claims or salts or N-oxides thereof, processes for preparing them and compositions containing them.

  杀虫、杀螨、杀线虫或杀软体动物的化合物，其化学式为(I)，其中Y为单键、C═O、C═S或C═(O)q，其中q为0、1或2；R1、R2、R3、R4、R8、R9和R10如权利要求中所定义，或其盐或N-氧化物，制备它们的方法以及含有它们的组合物。
• Chemical Compounds
  申请人：Maienfisch Peter

  公开号：US20090042938A1

  公开（公告）日：2009-02-12

  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 (II) is a 6 membered aromatic ring or is a 5 or 6 membered heteroaromatic ring; Z and Z′ are ═C— or —N— provided that both are not N; R 1 , R 2 R 3 , R 3a , R 4 , R 8 and Ra are specified organic groups and n and p are independently 0, 1, 2, 3 or 4; or salts or N-oxides thereof or compositions containing them in controlling insects, acarines, nematodes or molluscs. Novel compounds are also provided.

  使用化合物公式(I)，其中Y是单键，C═O，C═S或S(O)m，其中m为0，1或2；环(II)是6成员芳香环或是5或6成员杂芳环；Z和Z'是═C—或—N—，但两者都不是N；R1、R2、R3、R3a、R4、R8和Ra是指定的有机基团，n和p独立地为0、1、2、3或4；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也提供了新型化合物。
• CHEMICAL COMPOUNDS
  申请人：Maienfisch Peter

  公开号：US20120270885A1

  公开（公告）日：2012-10-25

  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 is a 6 membered aromatic ring or is a 5 or 6 membered heteroaromatic ring; Z and Z′ are provided that both are not N; R 1 , R 2 , R 3 , R 3a , R 4 , R 8 and Ra are specified organic groups and n and p are independently 0, 1, 2, 3 or 4; or salts or N-oxides thereof or compositions containing them in controlling insects, acarines, nematodes or molluscs. Novel compounds are also provided.

  公式IY的化合物的使用是指单键，C═O，C═S或S(O)m，其中m为0、1或2；环是6元芳香环或5或6元杂环；Z和Z′是提供的，只要两者都不是N；R1、R2，R3，R3a，R4，R8和Ra是指定的有机基团，n和p是独立的0、1、2、3或4；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。
• Chemical compounds
  申请人：Syngenta Crop Protection, Inc.

  公开号：US08129534B2

  公开（公告）日：2012-03-06

  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 (II) is a 6 membered aromatic ring or is a 5 or 6 membered heteroaromatic ring; Z and Z′ are ═C— or —N— provided that both are not N; R1, R2 R3, R3a, R4, R8 and Ra are specified organic groups and n and p are independently 0, 1, 2, 3 or 4; 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）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；环（II）是6成员芳香环或是5或6成员杂芳环；Z和Z′是═C—或—N—，但两者都不是N；R1、R2、R3、R3a、R4、R8和Ra是指定的有机基团，n和p独立地为0、1、2、3或4；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也提供了新的化合物。