1,2,3,4,5,6,7,8-octahydro-1,4;5,8-diethano-anthracene-9,10-diol | 155534-19-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 1,2,3,4,5,6,7,8-octahydro-1,4;5,8-diethano-anthracene-9,10-diol
• 英文别名: 9,10-Dihydroxy-1,2,3,4,5,6,7,8-octahydro-1,4:5,8-diaethano-anthracen；1,2,3,4,5,6,7,8-Octahydro-1,4:5,8-diaethano-anthracendiol-(9,10)；1,2,3,4,5,6,7,8-Octahydro-1,4;5,8-diaethano-anthracen-9,10-diol；Pentacyclo[10.2.2.25,8.02,11.04,9]octadeca-2,4(9),10-triene-3,10-diol
• CAS: 155534-19-3
• 化学式: C₁₈H₂₂O₂
• 分子量: 270.371
• InChiKey: JGXMYIXZQADKFO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  1,2,3,4,5,6,7,8-octahydro-1,4;5,8-diethano-anthracene-9,10-diol 在 吡啶 、 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 甲酸 、 溴 、 三乙胺 作用下， 以 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 60.0h， 生成 9,10-dibromo-1,2,3,4,5,6,7,8-octahydro-1,4:5,8-di(ethano)anthracene
  参考文献：
  名称：

  环氧的有机催化不对称水解

  摘要：

  环氧化合物的水解开环是重要的生物合成转化，也已在工业上应用。我们报道了该反应的第一个有机催化变体，它利用了我们最近发现的通过异二聚作用与手性磷酸对羧酸的活化作用。该方法学模拟了酶促机制，其中涉及酶结合的羧酸盐亲核试剂。新设计的磷酸催化剂显示高立体控制中的desymmetrization内消旋环氧化物。该方法在环状，酰基，芳族和脂族底物上显示出广泛的通用性。我们还将我们的方法应用于简单烯烃的第一个高度对映选择性的抗二羟基化反应中。

  DOI：

  10.1002/anie.201400170
• 作为产物：
  描述：

  dodecahydro-1,4;5,8-dietheno-anthracene-9,10-dione 在 palladium 10% on activated carbon 、 氢气 、 溴 作用下， 以 乙醇 、 氯仿 、 乙酸乙酯 为溶剂， 20.0 ℃ 、2.5 MPa 条件下， 反应 16.5h， 生成 1,2,3,4,5,6,7,8-octahydro-1,4;5,8-diethano-anthracene-9,10-diol
  参考文献：
  名称：

  一种含双环化侧基结构的二胺单体及其制备方法与应用

  摘要：

  本发明公开了一种含双环化侧基结构的二胺单体及其制备方法与应用。所述含双环化侧基结构的二胺单体具有如下式中任一者所示的结构： 本发明中由含双环化侧基结构的二胺单体制备一系列聚酰亚胺薄膜，由于大体积双环取代基与中心苯环结合，显著提高了二胺单体的刚性和位阻，使得所制备的聚酰亚胺薄膜具有高比表面积和气体渗透系数，其气体分离性能优于商品化气体分离膜以及相对应的六氟二酐气体分离膜，在工业氢气纯化和回收应用方面有较好的应用前景。

  公开号：

  CN116023277A

文献信息

• Convenient preparation of quinones via the catalytic autoxidation of hydroquinones with nitrogen oxides
  作者：Rajendra Rathore、Eric Bosch、Jay K. Kochi

  DOI：10.1016/s0040-4039(00)76211-3

  日期：1994.2

  An efficient, inexpensive, catalytic method for the autoxidation of hydroquinones utilizes the gaseous (NOx) catalyst which allows a simple workup procedure for quinone isolation merely by solvent removal.

  一种有效，廉价的对苯二酚自动氧化的催化方法利用了气态（NO x）催化剂，该方法允许简单的后处理步骤，仅通过去除溶剂即可分离出醌。
• Novel Catalysis of Hydroquinone Autoxidation with Nitrogen Oxides
  作者：E. Bosch、R. Rathore、J. K. Kochi

  DOI：10.1021/jo00088a039

  日期：1994.5

  An efficient catalytic method is described for the preparative conversion of hydroquinones to quinones with dioxygen under mild conditions. The use of the gaseous nitrogen oxide (NOx) catalyst allows a simple workup procedure for the isolation of quinones in essentially quantitative yields by merely removing the low-boiling solvent dichloromethane in vacuo. The mechanism of the catalytic autoxidation of hydroquinones is ascribed to the critical role of nitrosonium (NO+) in the one-electron oxidation of hydroquinone, followed by the reoxidation of the reduced nitric oxide (NO) with dioxygen. An extensive series of complex interchanges among various NOx species in nitrogen-(V), -(IV), -(III), and -(II) oxidation states, coupled with stepwise oxidation of hydroquinone via a successive series of one-electron/proton transfers, form the critical components of the catalytic cycle.
• Isolation of Novel Radical Cations from Hydroquinone Ethers. Conformational Transition of the Methoxy Group upon Electron Transfer
  作者：Rajendra Rathore、Jay K. Kochi

  DOI：10.1021/jo00119a017

  日期：1995.7

  Hydroquinone ethers as the bis-annulated derivatives R1-R3 are excellent electron donors by virtue of the facile oxidation to their radical cations R1(.+), R2(.-), and R3(.-) that are readily isolable as unusually robust SbCl6- and BF4- salts persistent in air for prolonged periods. Although the gas-phase vertical ionization potentials of the methyl ethers R1a and R2a are the same (IP = 7.83 +/- 0.01 eV), the oxidation potential of R1a in dichloromethane solution is less positive than that of R2a (E(1/2) = 1.11 and 1.30 V, respectively). The significantly lower value of E(1/2) for R1a relative to R2a, despite minimal changes in structure, is attributed to the conformational change that can occur in the radical cation. Indeed, X-ray crystallographic analysis of R1a, R2a, and R1a(.-) shows that the increased donor strength of R1a is derived from the enhanced (resonance) stabilization of R1a(.-), in which the methoxy group undergoes a 90 degrees rotation to the favorable coplanar conformation with respect to the aromatic ring. The subtle variation in the molecular structures of R1 and R2 accounts for the difference in nonbonded steric effects arising from the bridgehead alpha-hydrogens toward the methoxy groups.
• Alder; Stein, Justus Liebigs Annalen der Chemie, 1933, vol. 501, p. 247,274
  作者：Alder、Stein

  DOI：——

  日期：——
• Rathore Rajendra, Bosch Eric, Kochi Jay K., Tetrahedron Lett, 35 (1994) N 9, S 1335-1338
  作者：Rathore Rajendra, Bosch Eric, Kochi Jay K.

  DOI：——

  日期：——