benzonaphtho<2,3-h>bicyclo<4.4.1>undeca-3,8-dien-11-one | 108395-69-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: benzonaphtho<2,3-h>bicyclo<4.4.1>undeca-3,8-dien-11-one
• 英文别名: benzo[c]naphtho[2,3-h]bicyclo[4.4.1]undeca-3,8-dien-11-one；6,7,8,13,14,15-Hexahydro-7,14-methanobenzo[6,7]cyclodeca[1,2-b]naphthalen-17-one；pentacyclo[12.8.1.03,12.05,10.016,21]tricosa-3,5,7,9,11,16,18,20-octaen-23-one
• CAS: 108395-69-3
• 化学式: C₂₃H₂₀O
• 分子量: 312.411
• InChiKey: MWOVBEVAEJDHFU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  24
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 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：

  benzonaphtho<2,3-h>bicyclo<4.4.1>undeca-3,8-dien-11-one 在 lithium aluminium tetrahydride 、 titanium(III) chloride 作用下， 以 四氢呋喃 为溶剂， 反应 15.5h， 以46%的产率得到5,6,7,14,15,16-hexahydro-6,15-methanobenzonaphtho<2,3-f>cyclodecene
  参考文献：
  名称：

  Effect of 1,4-naphthoquinone annelation on the conformational behavnniour of carbonyl- and methano-bridged cyclodecadiene derivatives

  摘要：

  The Na2Cr2O7 oxidation of hexahydro-7,16-methanodinaphtho[2,3-a:2',3'-f] cyclodecene derivative 2, produced two bis-(1,4-naphthoquinone)s, 7 and 9, and monoquinone compound 8. Benzonaphtho derivative 3 gave two 1,4-naphthoquinone derivatives, 10 and 11, on oxidation.Flexible compounds 7-11 showed temperature-dependent H-1 NMR spectra due to equilibria among chair-boat, twin-chair, and boat-chair conformers, which were H-1 NMR spectroscopically characterized. A twin-chair conformer was detected in products 8, 9 and 10, but not in compounds 7 and 11. A broad absorption band due to an intramolecular C-T interaction in the twin-chair conformer was observed at lambda approximately 400 nm in the electronic spectra of the monoquinones, 8 and 10, but not in the bis(quinone) 9. Population of the twin-chair conformer increased with removal of the ester group on the bridgehead position. Reduction of the carbonyl group on the bridge also favoured the twin-chair conformation, indicating a repulsive interaction between the ester and the carbonyl group of the 1,4-naphthoquinone moiety. Upon irradiation with sunlight, compound 7 gave the [2 + 2]-photoadduct 15.

  DOI：

  10.1039/p19910001107
• 作为产物：
  描述：

  2,3-di(bromomethyl)naphthalene 在 氢氧化钾 、 sodium hydroxide 、 四丁基氯化铵 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 27.5h， 生成 benzonaphtho<2,3-h>bicyclo<4.4.1>undeca-3,8-dien-11-one
  参考文献：
  名称：

  [3.3]Orthocyclophanes with facing benzene and naphthalene rings

  摘要：

  DOI：

  10.1021/jo00389a004

文献信息

• MATAKA SHUNTARO; TAKAHASHI KAZUFUMI; MIMURA TAKAO; HIROTA TOSHIZUMI; TAKU+, J. ORG. CHEM., 52,(1987) N 13, 2653-2656
  作者：MATAKA SHUNTARO、 TAKAHASHI KAZUFUMI、 MIMURA TAKAO、 HIROTA TOSHIZUMI、 TAKU+

  DOI：——

  日期：——
• [3.3]Orthocyclophanes with facing benzene and naphthalene rings
  作者：Shuntaro Mataka、Kazufumi Takahashi、Takao Mimura、Toshizumi Hirota、Keisuke Takuma、Hiroshi Kobayashi、Masashi Tashiro、Kiyohisa Imada、Minoru Kuniyoshi

  DOI：10.1021/jo00389a004

  日期：1987.6
• Effect of 1,4-naphthoquinone annelation on the conformational behavnniour of carbonyl- and methano-bridged cyclodecadiene derivatives
  作者：Shuntaro Mataka、Seung Taeg Lee、Yuriko Tamura、Akihiko Tsuge、Masashi Tashiro

  DOI：10.1039/p19910001107

  日期：——

  The Na2Cr2O7 oxidation of hexahydro-7,16-methanodinaphtho[2,3-a:2',3'-f] cyclodecene derivative 2, produced two bis-(1,4-naphthoquinone)s, 7 and 9, and monoquinone compound 8. Benzonaphtho derivative 3 gave two 1,4-naphthoquinone derivatives, 10 and 11, on oxidation.Flexible compounds 7-11 showed temperature-dependent H-1 NMR spectra due to equilibria among chair-boat, twin-chair, and boat-chair conformers, which were H-1 NMR spectroscopically characterized. A twin-chair conformer was detected in products 8, 9 and 10, but not in compounds 7 and 11. A broad absorption band due to an intramolecular C-T interaction in the twin-chair conformer was observed at lambda approximately 400 nm in the electronic spectra of the monoquinones, 8 and 10, but not in the bis(quinone) 9. Population of the twin-chair conformer increased with removal of the ester group on the bridgehead position. Reduction of the carbonyl group on the bridge also favoured the twin-chair conformation, indicating a repulsive interaction between the ester and the carbonyl group of the 1,4-naphthoquinone moiety. Upon irradiation with sunlight, compound 7 gave the [2 + 2]-photoadduct 15.