8,9-dihydro-5,9-propano-5H-benzocyclohepten-7(6H)-one | 91146-27-9

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: 8,9-dihydro-5,9-propano-5H-benzocyclohepten-7(6H)-one
• 英文别名: Tricyclo[6.3.3.02,7]tetradeca-2,4,6-trien-10-one
• CAS: 91146-27-9
• 化学式: C₁₄H₁₆O
• 分子量: 200.28
• InChiKey: VXFUEUQBQYNPEU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  8,9-dihydro-5,9-propano-5H-benzocyclohepten-7(6H)-one 、 2-氨基苯甲腈 在 三氯化铝 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 12.0h， 以28%的产率得到rac-12-amino-6,7,8,9,10,11-hexahydro-7,11-o-benzenocycloocta[b]quinoline
  参考文献：
  名称：

  Synthesis and evaluation of tacrine–Huperzine a hybrids as acetylcholinesterase inhibitors of potential interest for the treatment of alzheimer’s disease

  摘要：

  Seventeen polycyclic compounds related to tacrine and huperzine A have been prepared as racemic mixtures and tested as acetylcholinesterase (AChE) inhibitors. The conjunctive pharmacomodulation of huperzine A (carbobicyclic substructure) and tacrine (4-aminoquinoline substructure) led to compound 7jy, 2.5 times less active than tacrine as AChE inhibitor, but much more active than its (Z)-stereoisomer (7iy). Derivatives 7dy and 7ey, lacking the ethylidene substituent, showed to be more active than tacrine. Many other structural modifications of 7jy led to less active compounds. Compounds 7dy and 7ey also showed to be much more active than tacrine in reversing the partial neuromuscular blockade induced by d-tubocurarine. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(98)00015-7
• 作为产物：
  描述：

  13-Hydroxy-tricyclo[6.3.3.0^2,7]tetradeca-2(7),3,5-trien-10-one 在 sodium hydroxide 、 一水合肼 、 三乙二醇 作用下， 反应 3.0h， 生成 8,9-dihydro-5,9-propano-5H-benzocyclohepten-7(6H)-one
  参考文献：
  名称：

  Bishop, Roger, Australian Journal of Chemistry, 1984, vol. 37, # 2, p. 319 - 325

  摘要：

  DOI：

文献信息

• Synthesis, Conformational Analysis and Transannular Reactions of 5,9-Propanobenzo[7]annulene Derivatives
  作者：Pelayo Camps、Diana Görbig、Victoria Muñoz-Torrero、Francesc Pérez

  DOI：10.1135/cccc19971585

  日期：——

  (5α,9α,11β)-11-Hydroxy-6,7,8,9-tetrahydro-5H-5,9-propanobenzo[7]annulen-7-one ethylene ketal (6a) and its 11α-methyl derivative (6b) were prepared from monoketal 3. These compounds underwent acid-catalyzed transannular reactions leading to 6,7,8,9-tetrahydro-5H-5,9-propanobenzo[7]annulene derivatives 5a, 8a and 5b, 8b, respectively, depending on the reaction conditions. The compounds 6a and 6b were dehydrated to 6,7,8,9-tetrahydro-5H-5,9-prop[1]enobenzo[7]annulen-7-one (9a) and its 11-methyl derivative (9b), respectively. The conformational analysis of the 5,9-propanobenzo[7]annulene derivatives by molecular mechanics calculations (MM3 program) and the ¹H NMR data show that hydroxyketal 6a and the related compound (5α,7β,9α)-6,7,8,9-tetrahydro-5H-5,9-propanobenzo[7]annulen-7-ol (4) exist mainly in the boat-chair conformation with the boat cycloheptenol ring, while for hydroxyketal 6b the chair-boat conformation (chair cycloheptenol ring) seems to be the preferred one.

  (5α,9α,11β)-11-羟基-6,7,8,9-四氢-5H-5,9-丙烷基苯并[7]茚-7-酮乙烯缩合物（6a）及其11α-甲基衍生物（6b）是从单酮3制备的。这些化合物经过酸催化的过渡环反应，根据反应条件，生成6,7,8,9-四氢-5H-5,9-丙烷基苯并[7]茚衍生物5a、8a和5b、8b。化合物6a和6b被脱水成6,7,8,9-四氢-5H-5,9-丙烯基苯并[7]茚-7-酮（9a）及其11-甲基衍生物（9b）。通过分子力学计算（MM3程序）和1H NMR数据对5,9-丙烷基苯并[7]茚衍生物进行构象分析，结果表明羟基缩酮6a及其相关化合物（5α,7β,9α）-6,7,8,9-四氢-5H-5,9-丙烷基苯并[7]茚-7-醇（4）主要存在于带有舟型-椅型构象的舟型环庚烯醇环中，而羟基缩酮6b则偏向于椅型-舟型构象（椅型环庚烯醇环）。