dinaphtho<2,3-c;2',3'-h>bicyclo<4.4.1>undeca-3,8-dien-11-one | 104663-78-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: dinaphtho<2,3-c;2',3'-h>bicyclo<4.4.1>undeca-3,8-dien-11-one
• 英文别名: dinaphthobicyclo<4.4.1>undecan-11-one；dinaphthobicyclo[4.4.1]undecan-11-one；Hexacyclo[12.12.1.03,12.05,10.016,25.018,23]heptacosa-3,5,7,9,11,16,18,20,22,24-decaen-27-one
• CAS: 104663-78-7
• 化学式: C₂₇H₂₂O
• 分子量: 362.471
• InChiKey: YBPUXLUUZMTPBS-UHFFFAOYSA-N

物化性质

• 熔点：
  293-294 °C(Solv: benzene (71-43-2))
• 沸点：
  602.1±55.0 °C(Predicted)
• 密度：
  1.206±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  28
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.22
• 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：

  dinaphtho<2,3-c;2',3'-h>bicyclo<4.4.1>undeca-3,8-dien-11-one 在 lithium aluminium tetrahydride 、 sodium dichromate 、 titanium(III) chloride 、 硫酸 作用下， 以 四氢呋喃 、 氯仿 、 水 为溶剂， 反应 16.0h， 生成 1,4,9,14-tetraoxo-1,4,6,7,8,9,14,15,16,17-decahydro-7,16-methanodinaphtho<2,3-a: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 为溶剂， 反应 3.5h， 生成 dinaphtho<2,3-c;2',3'-h>bicyclo<4.4.1>undeca-3,8-dien-11-one
  参考文献：
  名称：

  On the conformation of benzo-annelated bicyclo[4.4.1]undecanes, bicyclo[5.5.1]tridecanes, and a bicyclo[5.4.1]dodecane

  摘要：

  DOI：

  10.1021/jo00374a023

文献信息

• [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
• MATAKA SHUNTARO; TAKAHASHI KAZUFUMI; HIROTA TOSHIZUMI; TAKUMA KEISUKE; KO+, J. ORG. CHEM., 51,(1986) N 24, 4618-4622
  作者：MATAKA SHUNTARO、 TAKAHASHI KAZUFUMI、 HIROTA TOSHIZUMI、 TAKUMA KEISUKE、 KO+

  DOI：——

  日期：——
• 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：——
• On the conformation of benzo-annelated bicyclo[4.4.1]undecanes, bicyclo[5.5.1]tridecanes, and a bicyclo[5.4.1]dodecane
  作者：Shuntaro Mataka、Kazufumi Takahashi、Toshizumi Hirota、Keisuke Takuma、Hiroshi Kobayashi、Masashi Tashiro、Kiyohisa Imada、Minoru Kuniyoshi

  DOI：10.1021/jo00374a023

  日期：1986.11
• 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.