(8,9-dihydro-7H-benzocyclohepten-5-yl)-acetic acid | 53264-18-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (8,9-dihydro-7H-benzocyclohepten-5-yl)-acetic acid
• 英文别名: (8,9-Dihydro-7H-benzocyclohepten-5-yl)-essigsaeure；2-(8,9-dihydro-7H-benzo[7]annulen-5-yl)acetic acid
• CAS: 53264-18-9
• 化学式: C₁₃H₁₄O₂
• 分子量: 202.253
• InChiKey: RCMLYEIGIGCQOT-UHFFFAOYSA-N

物化性质

• 熔点：
  96-97 °C
• 沸点：
  377.8±21.0 °C(Predicted)
• 密度：
  1.139±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (8,9-dihydro-7H-benzocyclohepten-5-yl)-acetic acid 在 lithium aluminium tetrahydride 、 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 1-[2-(8,9-Dihydro-7H-benzocyclohepten-5-yl)-ethyl]-4-(2,3-dihydro-benzo[1,4]dioxin-5-yl)-piperazine
  参考文献：
  名称：

  Characterization of Potent and Selective Antagonists at Postsynaptic 5-HT1A Receptors in a Series of N4-Substituted Arylpiperazines

  摘要：

  Benzocycloalkyl and benzocycloalkenyl moities linked, directly or via an alkyl chain, to oxygen-bearing heteroarylpiperazines were synthesized, in an attempt to obtain potent and selective antagonists at postsynaptic 5-HT1A receptors. From the numerous arylpiperazines described in the literature, 1-(2,3-dihydro-1,4-benzodioxin-5-yl)pipe (3a) was chosen as a model of an arylpiperazine in view of its selectivity for 5-HT1A receptors versus alpha(1)-, alpha(2)-, and beta-adrenergic receptors, as well as dopamine D-1 and D-2 receptors. Two other closely-related arylpiperazines, 1-(1,5-benzodioxepin-6-yl)piperazine (3b) and 1-(benzofuran-7-yl)piperazine (3c), were also examined in this study. Al compounds showed high affinity at 5-HT1A sites (8.10 less than or equal to pK(i)s less than or equal to 9.35), and the majority behaved as antagonists in vivo in blocking the hypothermia induced by the 5-HT1A agonist 8-OH-DPAT in the absence of a marked effect alone at equivalent doses. An in vivo evaluation of dopamine D-2 receptor antagonist properties revealed that the majority of compounds was devoid of activity at this site, in marked contrast to BMY 7378 which displayed virtually no selectivity for 5-HT1A versus dopamine D-2 receptors. Moreover, six compounds of the present series, 8, 10, 11, 14, 25, and, 37, showed > 10-fold selectivity in vitro for 5-HT1A versus alpha(1)-adrenergic receptors. Compound 14 displayed an optimal compromise between potency (pK(i) = 8.75), marked antagonist activity, and selectivity toward alpha(1)-adrenergic (81-fold) and dopamine D-2 (195-fold) receptors. These characteristics clearly distinguish 14 from previously-reported ligands such as the postsynaptic 5-HT1A antagonist BMY 7378 and the weak partial agonist NAN 190 which, in contrast to the compounds of this series, belong to the well-exemplified class of imido derivatives of (o-methoxyphenyl)piperazines. The availability of 14 (S 15535) should facilitate the further elucidation of the functional role and potential therapeutic significance of 5-HT1A receptors.

  DOI：

  10.1021/jm00020a020
• 作为产物：
  描述：

  1-苯并环庚酮 在 甲酸 、 锌 作用下， 以 苯 为溶剂， 反应 2.0h， 生成 (8,9-dihydro-7H-benzocyclohepten-5-yl)-acetic acid
  参考文献：
  名称：

  乙氧基乙炔基甲醇-αβ-不饱和酯转化：伴随二氧化硒氧化的立体异构

  摘要：

  Benzsuberone与乙氧基乙炔基溴化镁反应生成1-乙氧基乙炔基-1-羟基-2,3-苯并环庚烯，与弱酸（二氧化碳）重排后，生成顺式-1,2-苯并3-苯并-3-环庚烯基乙酸乙酯（4，R ′＝ CO 2 Et，R 1＝ H）和相应的反式化合物。使用二氧化硒时，两种酯均会产生相同的γ-内酯，

  DOI：

  10.1016/s0040-4020(01)97022-x

文献信息

• AN ATTEMPTED SYNTHESIS OF 1, 10-CYCLOPENTENOHEPTALENE. 1,8-TETRAMETHYLENEAZULENE
  作者：A. G. ANDERSON、SHIH YI WANG

  DOI：10.1021/jo01367a015

  日期：1954.2