(-)-2,3:6,7-dibenzobicyclo[3.3.1]nona-2,6-diene-4,8-dione | 103773-00-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: (-)-2,3:6,7-dibenzobicyclo[3.3.1]nona-2,6-diene-4,8-dione
• 英文别名: (1S,9S)-tetracyclo[7.7.1.02,7.010,15]heptadeca-2,4,6,10,12,14-hexaene-8,16-dione
• CAS: 103773-00-8
• 化学式: C₁₇H₁₂O₂
• 分子量: 248.281
• InChiKey: PFCNXURTDZWJMG-GJZGRUSLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (-)-2,3:6,7-dibenzobicyclo[3.3.1]nona-2,6-diene-4,8-dione 在 lithium aluminium tetrahydride 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 31.0h， 生成 (+)-17,18:20,21-dibenzo-2,5,8,11,14-pentaoxatricyclo<13.3.3.1^16,19>docosa-17,20-diene
  参考文献：
  名称：

  含有 2,3:6,7-二苯并双环[3.3.1]nona-2,6-二烯残基作为手性亚基的双足和冠醚的合成和对映体识别

  摘要：

  报道了五种新的光学活性冠醚和六种光学活性双足。使用 (+)-(1S,4R,5S,8R)-2,3:6,7-dibenzobicyclo[3.3.1]nona-2,6-diene-4,8-​​diol 和（ +)-(1S,4R,5S,8R)-4,8-​​bis(hydroxymethyl)-2,3:6,7-dibenzobicyclo[3.3.1]nona-2,6-diene 作为手性亚基和双足体含有 2,3:6,7-二苯并双环 [3.3.1]nona-2,6-diene 残基作为手性锚定基团。这些化合物的对映体识别行为通过(±)-苯基甘氨酸甲酯和(±)-1,2-二苯基乙胺盐酸盐通过本体液膜的对映体差异转运来评估。

  DOI：

  10.1246/bcsj.62.83
• 作为产物：
  描述：

  2,4-diphenylpentanedioic acid 在 硫酸 作用下， 以 正辛烷 为溶剂， 反应 1.0h， 生成 (-)-2,3:6,7-dibenzobicyclo[3.3.1]nona-2,6-diene-4,8-dione
  参考文献：
  名称：

  Temperature-dependent racemic compound-conglomerate crystallization of 2,3:6,7-dibenzobicyclo[3.3.1]nona-2,6-diene-4,8-dione

  摘要：

  2,3:6.7-dibenzobicyclo[3.3.1]nona-2,6-diene-4,8-dione I is a new example of a compound capable of temperature-dependent racemate-conglomerate crystallization: at temperatures below 90degreesC crystals of the racemic compound (space group P (1) over bar, Z = 4) can be obtained. whereas above 100degreesC a conglomerate of (+)- and (-)-homochiral crystals (space group P2(1)2(1)2(1), Z=4) forms and therefore it undergoes spontaneous resolution upon crystallization. Enantioselective analytical gas chromatography on a single crystal has been proposed as a simple method for detection of conglomerate formation. The H-1 and C-13 NMR spectra of I are analvzed in detail and the crystal structures of both species (racemic compound and single enantiomer) have been solved by X-ray structural analysis. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00399-9

文献信息

• Optical Activity and Absolute Configuration of 2,3 :6,7-Dibenzobicyclo [3.3.1]nona-2,6-diene Derivatives
  作者：Hitoshi Tatemitsu、Fumio Ogura、Yasuhiro Nakagawa、Masazumi Nakagawa、Koichiro Naemura、Masao Nakazaki

  DOI：10.1246/bcsj.48.2473

  日期：1975.9

  7-Dibenzobicyclo[3.3.1]nona-2,6-diene-4,8-diol was synthesized and resolved via (−)-menthoxyacetate. Several kinds of optically active derivatives with the same absolute configuration were prepared from the (−)-diol and their chiroptical properties were recorded. The absolute configuration of this series of compounds was determined to be 1R, 5R by a chemical correlation with (R)-(−)-3-phenylbutanoic acid

  2,3 : 6,7-二苯并双环[3.3.1]nona-2,6-diene-4,8-​​diol 被合成并通过 (-)-menthoxyacetate 拆分。从(-)-二醇制备了几种具有相同绝对构型的旋光衍生物并记录了它们的手性。通过 (-)-1,3-二苯基戊二酸和 (-)-2 与 (R)-(-)-3-苯基丁酸的化学相关性，确定这一系列化合物的绝对构型为 1R、5R， 4-二苯基戊烷。
• Synthesis and enantiomer recognition of novel crown ethers containing the 5,6,11,12-tetrahydro-5,11-methanodibenzo[a,e]cyclo-octene subunit as the chiral centre
  作者：Koichiro Naemura、Rink? Fukunaga、Masataoshi Yamanaka

  DOI：10.1039/c39850001560

  日期：——

  The optically active crown ethers (4),(5),(7), (9) and (10) and the open-chain polyether(6), all of which incorporate the 5,6,11,12-tetrahydro-5,11-methanodibenzol[a,e]cyclo-octene molecular framework of known absolute configuration, were prepared, and their enantiomer recognition behavior with methyl(±)-phenylglycinate hydrochloride or (±)-1,2-diphenylethylamine hydrochloride was examined.

  光学活性冠醚（4），（5），（7），（9）和（10）以及开链聚醚（6），它们都掺有5,6,11,12-tetrahydro-5制备了已知绝对构型的11，甲基二苯并[ a，e ]环辛烯分子骨架，并研究了其与（±）-苯基甘氨酸甲酯盐酸盐或（±）-1,2-二苯乙胺盐酸盐的对映体识别行为。
• Synthesis of Chiral Cleft <i>C,N</i>-Palladium and Iridium Complexes from 2,3:6,7-Dibenzobicyclo[3.3.1]nona-2,6-diene-4,8-dione and Their Synthetic Applications
  作者：Congfa He、Bin Wang、Mingli Gao、Zhenhua Gu

  DOI：10.1021/acs.organomet.7b00024

  日期：2017.3.13

  A transition-metal-mediated functionalization of 2,3:6,7-dibenzobicyclo[3.3.1]nona-2,6-diene-4,8-dione is reported. By the use of the corresponding imine, iridium or palladium complexes were prepared, and they were well characterized by NMR and single-crystal X-ray crystallographic analysis. The catalytic activity of these two metal complexes was briefly investigated in hydrogenation and 1,2-addition reactions. Finally, the catalytic bromination of 2,3:6,7-dibenzobicyclo[3.3.1]nona-2,6-diene-4,8-dione was realized in the presence of NBS and Pd(OAc)(2). Subsequently a new class of V-shaped molecules with biphenanthridine skeletons were synthesized.
• The selective mono and difunctionalization of carbocyclic cleft molecules with pyridyl groups and X-ray crystallographic analysis
  作者：Priti Jilka、Claire Millington、Mark R.J. Elsegood、Josef W.A. Frese、Simon Teat、Marc C. Kimber

  DOI：10.1016/j.tet.2010.10.027

  日期：2010.11

  The diesterification and selective mono and dialkylation of carbocyclic analogues of Trager's base with pyridyl groups has been achieved in high yield and good selectivity giving access to a novel range of cleft molecules capable of binding events. Reaction conditions for the selective functionalization of this carbocyclic cleft molecule are discussed as well as the solid state structures of these newly synthesized ligands. (C) 2010 Elsevier Ltd. All rights reserved.
• Cleft molecules as organocatalysts in an asymmetric hetero-Diels–Alder reaction
  作者：Annika Friberg、Cecilia Olsson、Fredrik Ek、Ulf Berg、Torbjörn Frejd

  DOI：10.1016/j.tetasy.2007.03.018

  日期：2007.4

  The synthesis and application of chiral carbocyclic cleft molecules derived from 2,3:6,7-dibenzobicyclo[3.3.1]nona-2,6-diene-4,8-diene in the hetero-Diels-Alder reaction of benzaldehydes and aminodiene 14 is presented. Catalysis by single hydrogen-bond activation gave up to 52% ee. (c) 2007 Elsevier Ltd. All rights reserved.