5-(3,4-dichlorobenzylidene)-2-aza-bicyclo[2.2.2]octane-2-carboxylic acid tert-butyl ester | 617714-55-3

• 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: 5-(3,4-dichlorobenzylidene)-2-aza-bicyclo[2.2.2]octane-2-carboxylic acid tert-butyl ester
• 英文别名: 5-(3,4-Dichloro-benzylidene)-2-aza-bicyclo[2.2.2]octane-2-carboxylic acid tert-butyl ester；tert-butyl 5-[(3,4-dichlorophenyl)methylidene]-2-azabicyclo[2.2.2]octane-2-carboxylate
• CAS: 617714-55-3
• 化学式: C₁₉H₂₃Cl₂NO₂
• 分子量: 368.303
• InChiKey: KVTYVEBXCBTFLV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-(3,4-dichlorobenzylidene)-2-aza-bicyclo[2.2.2]octane-2-carboxylic acid tert-butyl ester 在 platinum(IV) oxide 氢气 、 三氟乙酸 、 tetramethylammonium triacetoxyborohydride 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 3.0h， 生成 N-(1-[5-(3,4-dichlorobenzyl)-2-aza-bicyclo[2.2.2]oct-2-ylmethyl]-2-methylpropyl)-4-methylbenzamide
  参考文献：
  名称：

  Design and synthesis of novel CCR3 antagonists

  摘要：

  As part of our investigation into the development of potent CCR3 antagonists, a series of piperidine analogues was designed and prepared. Exploration of the piperidine core examined both the basicity and the location of a nitrogen, as well as conformational variants. The bicyclo-piperidine 24c was found to be the most potent inhibitor of CCR3 with an IC50 of 0.0082 muM in the binding assay and 0.0024 muM in the chemotaxis assay. (C) 2003 Published by Elsevier Ltd.

  DOI：

  10.1016/s0960-894x(03)00748-0
• 作为产物：
  描述：

  4-硝基水杨酸 在 palladium on activated charcoal 、 rhodium on aluminium lithium aluminium tetrahydride 、 重铬酸吡啶 、 氯化亚砜 、 氢气 作用下， 以 四氢呋喃 、 二氯甲烷 、 溶剂黄146 、 乙酸乙酯 、 均三甲苯 为溶剂， 165.0 ℃ 、365.42 kPa 条件下， 反应 70.0h， 生成 5-(3,4-dichlorobenzylidene)-2-aza-bicyclo[2.2.2]octane-2-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Design and synthesis of novel CCR3 antagonists

  摘要：

  As part of our investigation into the development of potent CCR3 antagonists, a series of piperidine analogues was designed and prepared. Exploration of the piperidine core examined both the basicity and the location of a nitrogen, as well as conformational variants. The bicyclo-piperidine 24c was found to be the most potent inhibitor of CCR3 with an IC50 of 0.0082 muM in the binding assay and 0.0024 muM in the chemotaxis assay. (C) 2003 Published by Elsevier Ltd.

  DOI：

  10.1016/s0960-894x(03)00748-0

文献信息

• Bridged bicyclic amine derivatives useful as CCR-3 receptor antagonists
  申请人：——

  公开号：US20040176416A1

  公开（公告）日：2004-09-09

  Compounds having the formula (I), Ar—(F)(E)-(CR 3 R 4 )—(CHR 5 ) m -(T)-(Q)-Ar 1 , are useful as CCR-3 receptor antagonists, wherein T is a bridged heterocyclyl group having one N atom and a bridge of one to two bridgehead carbon atoms; Ar and Ar 1 are aryl or heteroaryl; F is alkylene, alkenylene, or a bond; E is —C(═O)N(R 10 )—, —SO 2 N(R 10 )—, —N(R 11 )C(═O)N(R 10 O)—, —N(R 11 )SO 2 N(R 10 )—, —N(R 11 )C(═S)N(R 10 )—, —N(R 11 )C(═O)—, —N(R 11 )SO 2 —, —N(R 12 )C(═O)CH(R 13 )—, or CH(R 13 )C(═O)N(R 12 )—; Q is —C(═O)— or C 1-2 alkylene; and R 3 , R 4 , R 5 , R 9 , R 10 , R 11 , R 12 , and R 13 are defined as set forth in the specification.

  具有以下化学式的化合物(I)，Ar—(F)(E)-(CR3R4)—(CHR5)m-(T)-(Q)-Ar1，可用作CCR-3受体拮抗剂，其中T是具有一个N原子和一个到两个桥头碳原子的桥接杂环基团；Ar和Ar1是芳基或杂环芳基；F是烷基，烯烃基或键；E是—C(═O)N(R10)—，—SO2N(R10)—，—N(R11)C(═O)N(R10O)—，—N(R11)SO2N(R10)—，—N(R11)C(═S)N(R10)—，—N(R11)C(═O)—，—N(R11)SO2—，—N(R12)C(═O)CH(R13)—或CH(R13)C(═O)N(R12)—；Q是—C(═O)—或C1-2烷基；R3，R4，R5，R9，R10，R11，R12和R13如规范中所述定义。