1,4,4a,5,8,8a-hexahydro-1,4:5,8-dimethanonaphthalene-4a,8a-dicarboxylic anhydride | 17397-36-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1,4,4a,5,8,8a-hexahydro-1,4:5,8-dimethanonaphthalene-4a,8a-dicarboxylic anhydride
• 英文别名: anti-sesquinorbornadiene
• CAS: 17397-36-3
• 化学式: C₁₄H₁₂O₃
• 分子量: 228.247
• InChiKey: JHYXIGYWOSCKAJ-JMSFITJXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.45
• 重原子数：
  17.0
• 可旋转键数：
  0.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1,4,4a,5,8,8a-hexahydro-1,4:5,8-dimethanonaphthalene-4a,8a-dicarboxylic anhydride 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 生成 decahydro-2,3-exo-6,7-exo-diepoxy-1,4-exo-5,8-endo-dimethanonaphthalene-4a,8a-dicarboxylic anhydride
  参考文献：
  名称：

  Reactivities of norbornene-type double bonds in propellane derivatives and their precursors; furan as a diene

  摘要：

  DOI：

  10.1021/ja00375a032
• 作为产物：
  描述：

  4,7-甲撑异苯并呋喃-1,3-二酮,4,7-二氢- 、 环戊二烯 以68%的产率得到1,4,4a,5,8,8a-hexahydro-1,4:5,8-dimethanonaphthalene-4a,8a-dicarboxylic anhydride
  参考文献：
  名称：

  Polycyclic aryl- and heteroarylpiperazinyl imides as 5-HT1A receptor ligands and potential anxiolytic agents: synthesis and structure-activity relationship studies

  摘要：

  A series of polycyclic aryl- and heteroarylpiperazinyl imides were prepared and tested in various receptor-binding and behavioral tests. Parameters measured included in vitro inhibition of D2 and 5-HT1A receptor binding, inhibition of apomorphine (APO) induced stereotyped and climbing behavior, and activity in blocking conditioned avoidance responding (CAR). Several compounds demonstrated moderate to high affinity for the 5-HT1A receptor binding site; compounds 27 and 36 containing the serotonin mimetic (o-methoxyphenyl)piperazinyl moiety and compounds 42 and 50 containing the 2-pyrimidinylpiperazinyl moiety displayed the highest affinity, being equal to that of the 5-HT1A agonist 8-OH-DPAT (Ki = 1-1.3 nM). In addition to affinity at 5-HT1A binding sites, many compounds were active in blocking CAR. Compound 34, 2-[4-[4-(2-pyrimidinyl)-1-piperazinyl]butyl]hexahydro-4,7-etheno-1H- cyclobut[f]isoindole-1,3(2H)-dione, demonstrated 3 times the activity of buspirone, blocking CAR in rats with an AB50 of 13 mg/kg. It also displayed high affinity for the 5-HT1A receptor (Ki = 16 nM), which is at least 20 times higher than its affinity for D2 (Ki = 345 nM) and 5-HT2 (Ki = 458 nM) receptors. Compound 34 was selected for further preclinical and pharmacokinetic evaluations for possible development as an anxiolytic agent. Structure-activity relationships within this series are discussed.

  DOI：

  10.1021/jm00402a023

文献信息

• Experimental evidence establishing an upper limit to the activation barrier for the butterfly bending of the double bond in anti-sesquinorbornene.
  作者：Richard Vaughan Williams、Chiu-Lien Ann Sung、Henry A. Kurtz、Thomas M. Harris

  DOI：10.1016/0040-4039(88)80004-2

  日期：1988.1

  Low temperature13C NMR and theoretical results are presented which imply that in the groundstate of anti-sesquinorbornene the double bond is either pyramidal with a very low barrier to inversion or planar.

  给出了低温13 C NMR和理论结果，这表明在抗次喹啉降冰片烯的基态中，双键要么呈锥体结构，对反演的阻隔性就很低，要么呈平面状。