(E)-1'-(3-(4-chlorophenyl)allyl)-5-fluorospiro[indoline-3,4'-piperidine] | 637360-23-7

• 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: (E)-1'-(3-(4-chlorophenyl)allyl)-5-fluorospiro[indoline-3,4'-piperidine]
• 英文别名: 1'-[(E)-3-(4-chlorophenyl)prop-2-enyl]-5-fluorospiro[1,2-dihydroindole-3,4'-piperidine]
• CAS: 637360-23-7
• 化学式: C₂₁H₂₂ClFN₂
• 分子量: 356.87
• InChiKey: DISPPDHCSOHOAW-OWOJBTEDSA-N

物化性质

• 沸点：
  516.6±50.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  15.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-1'-(3-(4-chlorophenyl)allyl)-5-fluorospiro[indoline-3,4'-piperidine] 在 silica gel 、 zinc(II) chloride 、 sodium nitrite 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 3.5h， 以95%的产率得到1-nitroso-5-fluoro-1'-[trans-3-(4-chlorophenyl)allyl]spiro[indoline-3,4'-piperidine]
  参考文献：
  名称：

  [EN] SPIROINDOLINEPIPERIDINE DERIVATIVES
  [FR] DERIVES DE SPIROINDOLINEPIPERIDINE

  摘要：

  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。

  公开号：

  WO2003106457A1
• 作为产物：
  描述：

  1-氯-4-[(1E)-3-氯-1-丙烯基]-苯 在 盐酸 、 potassium tert-butylate 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 氯仿 、 水 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

文献信息

• 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。
• SPIROINDOLINEPIPERIDINE DERIVATIVES
  申请人：Hughes David John

  公开号：US20120010220A1

  公开（公告）日：2012-01-12

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

  式(I)中的杀虫、杀螨、杀线虫或杀软体动物化合物，其中Y是单键、C═O、C═S或S(O)q，其中q为0、1或2；而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，以及制备它们的过程和包含它们的组合物。
• US9174987B2
  申请人：——

  公开号：US9174987B2

  公开（公告）日：2015-11-03
• US9686990B2
  申请人：——

  公开号：US9686990B2

  公开（公告）日：2017-06-27
• [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。