(5-cyano-10,11-dihydrodibenzo[a,d]cycloheptene-5-yl)-acetic acid ethyl ester | 138707-13-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 二苯并环庚烯
• 英文名称: (5-cyano-10,11-dihydrodibenzo[a,d]cycloheptene-5-yl)-acetic acid ethyl ester
• 英文别名: Ethyl 2-(2-cyano-2-tricyclo[9.4.0.03,8]pentadeca-1(15),3,5,7,11,13-hexaenyl)acetate
• CAS: 138707-13-8
• 化学式: C₂₀H₁₉NO₂
• 分子量: 305.376
• InChiKey: LFWVHTKCWACSPL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  50.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (5-cyano-10,11-dihydrodibenzo[a,d]cycloheptene-5-yl)-acetic acid ethyl ester 在 palladium on activated charcoal 盐酸 、 硼烷四氢呋喃络合物 、 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 80.0h， 生成 Spiro[dibenzosuberane-5,3'-pyrrolidine]
  参考文献：
  名称：

  Structural determinants for high 5-HT 2A receptor affinity of spiro[9,10-dihydroanthracene]-9,3 ′ -pyrrolidine (SpAMDA)

  摘要：

  The synthesis and 5-HT2A receptor affinities of ring altered derivatives of spiro[9,10-dihydroanthracene]-9,3'-pyrrolidine (4), a structurally unique tetracyclic 5-HT2A receptor antagonist, are described. The characteristics of the parent compound prove to be necessary for optimal 5-HT2A receptor affinity. However, expansion of the size of the pyrrolidine and central rings produce compounds with reasonably high 5-HT2A receptor affinities. In addition, the parent compound is shown to have high 5-HT2 receptor selectivity. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.02.014
• 作为产物：
  描述：

  10,11-二氢-5H-二苯并[A,D]环庚烯-5-甲腈 、 溴乙酸乙酯 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 5.0h， 以55%的产率得到(5-cyano-10,11-dihydrodibenzo[a,d]cycloheptene-5-yl)-acetic acid ethyl ester
  参考文献：
  名称：

  Structural determinants for high 5-HT 2A receptor affinity of spiro[9,10-dihydroanthracene]-9,3 ′ -pyrrolidine (SpAMDA)

  摘要：

  The synthesis and 5-HT2A receptor affinities of ring altered derivatives of spiro[9,10-dihydroanthracene]-9,3'-pyrrolidine (4), a structurally unique tetracyclic 5-HT2A receptor antagonist, are described. The characteristics of the parent compound prove to be necessary for optimal 5-HT2A receptor affinity. However, expansion of the size of the pyrrolidine and central rings produce compounds with reasonably high 5-HT2A receptor affinities. In addition, the parent compound is shown to have high 5-HT2 receptor selectivity. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.02.014

文献信息

• Spiro dibenzosuberane derivatives
  申请人：SHIONOGI SEIYAKU KABUSHIKI KAISHA

  公开号：EP0456183B1

  公开（公告）日：1995-10-04
• Structural determinants for high 5-HT 2A receptor affinity of spiro[9,10-dihydroanthracene]-9,3 ′ -pyrrolidine (SpAMDA)
  作者：Srinivas Peddi、Bryan L Roth、Richard A Glennon、Richard B Westkaemper

  DOI：10.1016/j.bmcl.2004.02.014

  日期：2004.5

  The synthesis and 5-HT2A receptor affinities of ring altered derivatives of spiro[9,10-dihydroanthracene]-9,3'-pyrrolidine (4), a structurally unique tetracyclic 5-HT2A receptor antagonist, are described. The characteristics of the parent compound prove to be necessary for optimal 5-HT2A receptor affinity. However, expansion of the size of the pyrrolidine and central rings produce compounds with reasonably high 5-HT2A receptor affinities. In addition, the parent compound is shown to have high 5-HT2 receptor selectivity. (C) 2004 Elsevier Ltd. All rights reserved.