dibenzobicyclo<2.2.2>octane-cis-2,3-diol | 2732-95-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: dibenzobicyclo<2.2.2>octane-cis-2,3-diol
• 英文别名: 9,10-dihydro-9,10-ethanoanthracene-cis-11,12-diol；9,10-cis-Dihydro-9,10-ethano-11,12-anthracendiol；(15R,16S)-tetracyclo[6.6.2.02,7.09,14]hexadeca-2,4,6,9,11,13-hexaene-15,16-diol
• CAS: 2732-95-8
• 化学式: C₁₆H₁₄O₂
• 分子量: 238.286
• InChiKey: PVCRDGNYGWVRCO-STONLHKKSA-N

物化性质

• 熔点：
  200.5-201.5 °C
• 沸点：
  409.4±45.0 °C(Predicted)
• 密度：
  1.349±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  dibenzobicyclo<2.2.2>octane-cis-2,3-diol 在 lead(IV) acetate 作用下， 生成 9,10-dihydroanthracen-9,10-dicarbaldehyde
  参考文献：
  名称：

  FR2446285

  摘要：

  公开号：
• 作为产物：
  描述：

  9,10-二氢-9,10-乙烯桥蒽 在 四氧化锇 作用下， 以 吡啶 为溶剂， 反应 5.0h， 以90%的产率得到dibenzobicyclo<2.2.2>octane-cis-2,3-diol
  参考文献：
  名称：

  Distortion of Olefin and Carbonyl .pi.-Orbitals in Dibenzobicyclo[2.2.2]octatrienes and Dibenzobicyclo[2.2.2]octadienones. Unsymmetrization of .pi. Lobes Arising from .pi.-.pi. Orbital Interactions

  摘要：

  We have detected the unsymmetrical pi faces of the olefin group in 2-substituted dibenzobicyclo-[2.2.2]octatrienes (2-substituted 9,10-dihydro-9,10-ethenoanthracenes) and the carbonyl groups of 2-substituted and 3-substituted dibenzobicycla[2.2.2]octadienones (2-substituted and 3-substituted 9,10-dihydro-9,10-(11-ketoethano)anthracenes), wherein alpha-type overlaps of the pi orbitals are involved, in a similar manner to longicyclic conjugation. An intrinsically nonequivalent substituent at distal positions modulates the epoxidation and dihydroxylation of the olefin group and the reduction of the carbonyl group. Both systems exhibit similar substituent effects: an ''electron-withdrawing'' substituent such as a nitro or fluoro group gave a large to moderate bias (preferred syn attack with respect to the substituent) whereas an ''electron-donating'' methoxy substituent exhibited a negligible bias. Herein we interpret these biases or nonbiases in terms of unsymmetrization of pi lobes of the olefin and carbonyl pi orbitals, arising from nonequivalent pi-pi interactions rather than from an electron-donating or -withdrawing effect.

  DOI：

  10.1021/jo00093a032

文献信息

• Stereocontrolled synthesis of highly functionalized cyclohexenes. A short synthesis of a chorismic acid precursor
  作者：Gary H. Posner、Todd D. Nelson

  DOI：10.1016/s0040-4020(01)85582-4

  日期：——

  allowing isolation of the structurally and stereochemically rich initial bicyclic adducts 8. These bicyclic adducts are shown to be useful building units as exemplified by a very short and high-yield preparation of a chorismic acid precursor.

  已经开发了一种方便且温和的热方法，可将富电子的1,2-二加氧烯烃7立体选择性2 + 4-环加成至缺电子的3-磺酰基-2-吡喃酮6，从而可以分离结构和立体化学丰富的初始双环加合物8。这些双环加合物被证明是有用的结构单元，例如以短而高收率制备的鸟苷酸前体为例。
• Rhodium(I)-Catalyzed [2+2+1]-Carbonylative Cycloaddition of Diynes with Anthracene α-Diketone as the Source of CO
  作者：Tsumoru Morimoto、JingWen Jia、Yoshiko Yamaguchi、Tatsuya Ueda、Hiroko Yamada、Kiyomi Kakiuchi

  DOI：10.1055/a-1938-1294

  日期：2022.12

  We report on the use of anthracene α-diketone as a source of carbon monoxide (CO) in carbonylation reactions. Photoirradiation by a 5 W blue LED of a diyne in the presence of anthracene α-diketone and a rhodium(I) catalyst resulted in a [2+2+1]-carbonylative cycloaddition of the diyne to CO released from the anthracene α-diketone to give a high yield (up to 99%) of the corresponding cyclopentadienone

  我们报告了在羰基化反应中使用蒽 α-二酮作为一氧化碳 (CO) 的来源。在蒽 α-二酮和铑 (I) 催化剂存在下，二炔的 5 W 蓝色 LED 光辐照导致二炔与从蒽 α-二酮释放的 CO 发生 [2+2+1]-羰基环加成反应得到相应的环戊二烯酮的高产率（高达 99%）。这是使用蒽 α-二酮的无 CO 气体羰基化反应的首次演示。光照是蒽α-二酮生成CO和催化活性的主要因素。卤素灯、荧光灯或太阳光也可作为该反应的光源。有了这个系统，就不需要额外的试剂来产生 CO。
• Wulff, Guenter; Birnbrich, Paul, Chemische Berichte, 1992, vol. 125, # 2, p. 473 - 478
  作者：Wulff, Guenter、Birnbrich, Paul

  DOI：——

  日期：——
• Transition Metal Mediated <i>Exo </i>Selective Diels−Alder Reactions:  Preparation of 2-Cobalt-Substituted 1,3-Dienes Containing <i>C</i>₂ Symmetric 2,3-Dibenzobicyclo[2.2.2]octanedione Dioxime Equatorial Ligands and Their Use in Thermal and Lewis Acid Catalyzed 4 + 2 Cycloadditions
  作者：Marcus W. Wright、Mark E. Welker

  DOI：10.1021/jo951505o

  日期：1996.1.1

  The preparation of C-2 symmetric 2,3-dibenzobicyclo[2.2.2]octanedione dioxime is reported. This ligand is then used in the preparation of a (pyridine)(glyoxime)(2)cobalt(III) chloride complex. The chloride is reduced to a cobaloxime anion which reacted with allenic electrophiles to produce (pyridine)(glyoxime)(2)cobalt-1,3-dienyl complexes. Thermal and Lewis acid catalyzed Diels-Alder reactions of these dienyl complexes as well as the complexes with glyoxime = diphenylglyoxime and dimethylglyoxime are reported. In most cases these Diels-Alder reactions are anti (exo) selective, and in many cases diastereoselectivities are >20:1. Cycloadduct demetalation reactions are also reported which preserve cycloaddition stereochemistry and provide cobalt complexes which can be recycled into the starting dienyl complex.
• LASNE, M. -C.;RIPOLL, J. -L., TETRAHEDRON LETT., 1982, 23, N 15, 1587-1588
  作者：LASNE, M. -C.、RIPOLL, J. -L.

  DOI：——

  日期：——