2-(2-chloroethyl)quinuclidine | 733679-99-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 奎宁环
• 英文名称: 2-(2-chloroethyl)quinuclidine
• 英文别名: 2-(2-Chlorethyl)-chinuclidin；2-Chloraethyl-chinuclidin；2-Chlorethyl-chinuclidin；2-chloroethyl-quinuclidine；2-(2-chloroethyl)-1-azabicyclo[2.2.2]octane
• CAS: 733679-99-7
• 化学式: C₉H₁₆ClN
• 分子量: 173.686
• InChiKey: VNMJGMFRVSCCIK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(2-chloroethyl)quinuclidine 、 7-Chloro-4-hydroxy-2-oxo-3-(3,4,5-trimethyl-phenyl)-1,2-dihydro-quinoline-6-carboxylic acid pyrimidin-4-ylamide 在 potassium hydrogencarbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以55%的产率得到4-[2-(1-Aza-bicyclo[2.2.2]oct-2-yl)-ethoxy]-7-chloro-2-oxo-3-(3,4,5-trimethyl-phenyl)-1,2-dihydro-quinoline-6-carboxylic acid pyrimidin-4-ylamide
  参考文献：
  名称：

  Identification of neutral 4-O-alkyl quinolone nonpeptide GnRH receptor antagonists

  摘要：

  A series of neutral, nonbasic quinolone GnRH antagonists were prepared via Mitsunobu alkylation of protected and unprotected 4-hydroxy quinolone intermediates. The synthetic route was improved by utilization of unique reactivity and convergency afforded by the use of mono and bis-trimethylsilylethyl protected quinolones. Potent neutral GnRH antagonists were identified, including ether and lactam derivatives, that show similar in vitro binding affinity and functional activity as compared to the earlier basic 4-aminoalkyl quinolone series of nonpeptide GnRH antagonists. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.08.056
• 作为产物：
  描述：

  2-(2-Hydroxyethyl)-chinuclidin 在 氯化亚砜 作用下， 以 氯仿 为溶剂， 生成 2-(2-chloroethyl)quinuclidine
  参考文献：
  名称：

  Phenothiazine derivative

  摘要：

  苯噻嗪衍生物的结构式描述如下：##SPC1## 其中X.sub.1和X.sub.2，可以相同也可以不同，为H、R、F、Cl、Br、OR、CN、--COR、CH.sub.3、--S--R、--SOR、--SO.sub.2 R或--SO.sub.2 N(CH.sub.3).sub.2，其中R是具有1至4个碳原子的烷基基团，奎尼啉环被羰基--(CH.sub.2).sub.x-- 取代在2-或3-位置，当该基团在2-位置取代时，x为1或2，当该基团在3-位置取代时，x为0或1（由于电子障碍），它们的酸盐和季铵盐具有有价值的药理特性。特别是，这些化合物具有抗组胺、抗胆碱能、肾上腺抑制、神经镇静、镇定和/或解痉作用。这些化合物是通过将适当的苯噻嗪与结构式为##SPC2## 的奎尼啉衍生物缩合而制备的，其中x具有上述定义，Z为卤原子或活性酯基。

  公开号：

  US03987042A1

文献信息

• Phenothiazine derivative
  申请人：——

  公开号：US03987042A1

  公开（公告）日：1976-10-19

  Phenothiazine derivatives are described of the formula ##SPC1## In which X.sub.1 and X.sub.2, which may be the same or different, are H, R, F, Cl, Br, OR, CN, --COR, CH.sub.3, --S--R, --SOR, --SO.sub.2 R or --SO.sub.2 N(CH.sub.3).sub.2, where R is an alkyl group having from 1 to 4 carbon atoms, and the quinuclidine ring is substituted by the group --(CH.sub.2).sub.x -- in the 2- or 3- position, x being 1 or 2 when said group is substituted in the 2-position and being 0 or 1 when said group is substituted in the 3-position (because of electronic hindrance), and their acid addition and quaternary ammonium salts, have valuable pharmacological properties. In particular, these compounds have anti-histaminic, anti-cholinergic, adrenolytic, neuro-sedative, tranquillizing and/or spasmolytic properties. These compounds are prepared by condensing an appropriate phenothiazine with a quinuclidine derivative of the formula ##SPC2## In which x has the above-stated meaning and Z is a halogen atom or a reactive ester group.

  苯噻嗪衍生物的结构式描述如下：##SPC1## 其中X.sub.1和X.sub.2，可以相同也可以不同，为H、R、F、Cl、Br、OR、CN、--COR、CH.sub.3、--S--R、--SOR、--SO.sub.2 R或--SO.sub.2 N(CH.sub.3).sub.2，其中R是具有1至4个碳原子的烷基基团，奎尼啉环被羰基--(CH.sub.2).sub.x-- 取代在2-或3-位置，当该基团在2-位置取代时，x为1或2，当该基团在3-位置取代时，x为0或1（由于电子障碍），它们的酸盐和季铵盐具有有价值的药理特性。特别是，这些化合物具有抗组胺、抗胆碱能、肾上腺抑制、神经镇静、镇定和/或解痉作用。这些化合物是通过将适当的苯噻嗪与结构式为##SPC2## 的奎尼啉衍生物缩合而制备的，其中x具有上述定义，Z为卤原子或活性酯基。
• Identification of neutral 4-O-alkyl quinolone nonpeptide GnRH receptor antagonists
  作者：Robert J. DeVita、Mamta Parikh、Jinlong Jiang、Jason A. Fair、Jonathan R. Young、Thomas F. Walsh、Mark T. Goulet、Jane-L. Lo、Ning Ren、Joel B. Yudkovitz、Jisong Cui、Yi T. Yang、Kang Cheng、Susan P. Rohrer、Matthew J. Wyvratt

  DOI：10.1016/j.bmcl.2004.08.056

  日期：2004.11

  A series of neutral, nonbasic quinolone GnRH antagonists were prepared via Mitsunobu alkylation of protected and unprotected 4-hydroxy quinolone intermediates. The synthetic route was improved by utilization of unique reactivity and convergency afforded by the use of mono and bis-trimethylsilylethyl protected quinolones. Potent neutral GnRH antagonists were identified, including ether and lactam derivatives, that show similar in vitro binding affinity and functional activity as compared to the earlier basic 4-aminoalkyl quinolone series of nonpeptide GnRH antagonists. (C) 2004 Elsevier Ltd. All rights reserved.