<6>(1,2)naphthalenophane | 16271-28-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: <6>(1,2)naphthalenophane
• 英文别名: 6,7,8,9,10,11-Hexahydro-cyclooctanaphthalin；6,7,8,9,10,11-Hexahydrocycloocta[b]naphthalene
• CAS: 16271-28-6
• 化学式: C₁₆H₁₈
• 分子量: 210.319
• InChiKey: WZYMBSDEXLSWMN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  5-Chloro-6,7,8,9,10,11-hexahydro-cycloocta[b]naphthalene 在 palladium on activated charcoal 肼 作用下， 以 乙醇 为溶剂， 生成 <6>(1,2)naphthalenophane
  参考文献：
  名称：

  1,3-Bridged aromatic systems. VIII. Rearrangements in strained systems

  摘要：

  DOI：

  10.1021/jo00946a031

文献信息

• Electrophilic aromatic substitution. Part 36. Protiodetritiation of some annelated meta-cyclophanes: effect of ring-buckling on reactivity, and the first example of electrophilic substitution through a hole
  作者：Andrew P. Laws、Adrian P. Neary、Roger Taylor

  DOI：10.1039/p29870001033

  日期：——

  electrophile at one face of the loop formed between the alkyl chain and the aromatic ring, and departure of the leaving group (triton) from the opposite face, i.e. substitution occurs through a ‘hole’. This is the first example of electrophilic substitution at an enclosed site. The fact that steric effects in both reagent and product in hydrogen exchange are almost identical is postulated as a primary reason

  已经制备了一系列的1，3-桥联的萘，其中的烷基桥含有十个，八个或七个亚甲基，而tri位于2-或4-位。已经测量了它们在70°C的无水三氟乙酸中的降解速率。随着桥的尺寸减小，在4-位交换的部分速率因子增加。1.28×10 7（[CH 2 ] 10）2.71×10 7（[CH 2 ] 8），2.97×10 7（[CH 2 ] 7）; cf. 1.15×10 7对于1,3-二甲基萘，对应的σ +值为–0.812，–0.849，–0.854和–0.807。随着芳环变得更弯曲，这与增加的基态芳族性损失相一致。在2位上，部分速率因子为2.37×10 5（[CH 2 ] 10），2.92×10 5（[CH 2 ] 8）和1.50×10 5（[CH 2 ] 7）；cf. 1,3-二甲基萘为2.82×10 5，对应的σ +值为–0.614，–0.625，–0.592和–0.623。此处的结果反映了由于基态芳
• Bidentate Lewis Acid-Catalyzed Inverse Electron-Demand Diels–Alder Reaction of Phthalazines and Cyclooctynes
  作者：Hermann A. Wegner、Michel Große

  DOI：10.1055/a-2204-9522

  日期：——

  Herein we report a method for facilitating the inverse-electron-demand Diels–Alder reaction of 1,2-diazines and cyclooctynes by utilizing a boron-based bidentate Lewis acid catalyst. Readily available electron-deficient and electron-rich phthalazines proved to be suitable substrates in this transformation. The described method enables the facile construction of diversely substituted polycyclic aromatic

  在此，我们报道了一种利用硼基二齿路易斯酸催化剂促进1,2-二嗪和环辛炔的逆电子需求狄尔斯-阿尔德反应的方法。容易获得的缺电子和富电子二氮杂萘被证明是该转化中合适的底物。所述方法能够轻松构建稠合到八元碳环的不同取代的多环芳烃。
• A photoannulation route to naphthalenes from cyclic ketones
  作者：Robert J. Olsen、John C. Minniear、W. Mack Overton、John M. Sherrick

  DOI：10.1021/jo00003a018

  日期：1991.2

  A three-step naphthalene annulation of cyclic ketones has been developed. Aldol condensation with an aromatic aldehyde followed by Wittig olefination produces a 1,3-diene, which undergoes oxidative photocyclization to produce a naphthalene derivative. Ketone ring sizes of C5 to C8 were annulated successfully. The sequence was also applied successfully to three methyl-substituted derivatives and one polycyclic case.
• Krebs,A.; Byrd,D., Justus Liebigs Annalen der Chemie, 1967, vol. 707, p. 66 - 74
  作者：Krebs,A.、Byrd,D.

  DOI：——

  日期：——
• OLSEN, ROBERT J.;MINNIEAR, JOHN C.;OVERTON, W. MACK;SHERRICK, JOHN M., J. ORG. CHEM., 56,(1991) N, C. 989-991
  作者：OLSEN, ROBERT J.、MINNIEAR, JOHN C.、OVERTON, W. MACK、SHERRICK, JOHN M.

  DOI：——

  日期：——