4H-环戊并(def)菲-4-醇 | 64884-42-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 中文名称: 4H-环戊并(def)菲-4-醇
• 英文名称: 4H-cyclopentaphenanthren-4-ol
• 英文别名: 4H-Cyclopenta(def)phenanthren-4-ol；tetracyclo[10.2.1.05,14.08,13]pentadeca-1,3,5(14),6,8(13),9,11-heptaen-15-ol
• CAS: 64884-42-0
• 化学式: C₁₅H₁₀O
• 分子量: 206.244
• InChiKey: UWAIRMQUVIHZAR-UHFFFAOYSA-N

物化性质

• 沸点：
  449.8±14.0 °C(Predicted)
• 密度：
  1.391±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 海关编码：
  2906299090

反应信息

• 作为反应物：
  描述：

  4H-环戊并(def)菲-4-醇 以85%的产率得到
  参考文献：
  名称：

  MINABE, MASAHIRO;YOSHIDA, MASAAKI;AMIMOTO, TSUKASA;NAGATA, TOSHIHIRO;KOBO+, BULL. CHEM. SOC. JAP., 61,(1988) N 3, 879-883

  摘要：

  DOI：
• 作为产物：
  描述：

  4H-环五菲 生成 4H-环戊并(def)菲-4-醇
  参考文献：
  名称：

  Synthesis of ketone and alcohol derivatives of methylene-bridged polyarenes, potentially new classes of active metabolites of carcinogenic hydrocarbons

  摘要：

  Methods for the syntheses of bridge ketone and alcohol derivatives of methylene-bridged polyarenes from the parent hydrocarbons are described. The polyarenes investigated include 4H-cyclopenta[def]phenanthrene (1a), fluorene (2a), 7H-benzo[c]fluorene (3a), 4H-cyclopenta[def]chrysene (4a), 11H-Benz[bc]aceanthrylene (5a), 10H-indeno[1,2,7,7a-bcd]pyrene (6a), 11H-dibenzo[bc,l]aceanthrylene (7a), 4H-fluoreno[4,4a,4b,5-abc]anthracene (8a), and 7H-dibenzo[a,g]fluorene (9a). The bridge ketone derivatives are most efficiently synthesized via treatment of the parent hydrocarbons with n-butyllithium and reaction of the resulting anionic intermediates with molecular oxygen. The direct formation of ketones rather than the expected hydroperoxides from reaction of the bridge anions With O2 presumably involves intra- or intermolecular abstraction of a proton from the benzylic site of the intermediate by the peroxy anion leading to loss of hydroxide ion with formation of a carbonyl group. Yields are generally high except in the cases of 1a and 4a; the former affords as the principal product a dimeric alcohol arising from reaction of the anion of 1a with the corresponding ketone lb. The related bridge alcohols am readily obtained in yields of 75-95% by reduction of the crude products from the preceding oxidations with NaBH4.

  DOI：

  10.1021/jo00049a045

文献信息

• Crystal structure of and conformational equilibria in 1,1?-dihydroxybis(4H-cyclopenta[def]phenanthrene) and related derivatives
  作者：Mary Hoang、Gabriela Mladenova、Alan C. Hopkinson、Jailal Ramnauth、Edward Lee-Ruff

  DOI：10.1002/mrc.839

  日期：2001.5

  The aromatic protons and carbons in the NMR spectra of certain clamped 1,1,2,2‐tetraarylethane‐1,2‐diols undergo intermediate exchange at ambient temperature as the result of conformational equilibrium between two enantiomeric gauche forms. The crystal structures for two of these derivatives show the conformational preference for this geometry in the solid state in contrast to other reported unclamped

  由于两种对映体 gauche 形式之间的构象平衡，某些钳位的 1,1,2,2-四芳基乙烷-1,2-二醇的 NMR 光谱中的芳香质子和碳在环境温度下进行中间交换。与其他报道的未钳位的 1,1,2,2-四芳基乙烷-1,2-二醇相比，这些衍生物中的两种衍生物的晶体结构显示出这种几何形状在固态时的构象偏好。这些邻位二醇的构象偏好与 1,1,2,2-四芳基乙烷的构象偏好相似。然而，在不对称取代的二苯基甲基芴系列中，与烃相比，邻二醇更喜欢采用 gauche 构象，烃更喜欢归因于前者的氢键效应的反几何。该系列二醇和乙烷的构象偏好的 AM1 计算结果包括在内，并与实验观察结果一致。版权所有 © 2001 John Wiley & Sons, Ltd.
• The Fries Rearrangement of 4<i>H</i>-Cyclopenta[<i>def</i>]phenanthrenyl Acetate
  作者：Masahiro Minabe、Masaaki Yoshida、Tsukasa Amimoto、Toshihiro Nagata、Masamichi Kobori

  DOI：10.1246/bcsj.61.879

  日期：1988.3

  4H-cyclopenta[def]phenanthren-1-yl acetate gave 2- and 7-acetyl derivatives. The reaction of isomeric 2-acetoxy compound afforded 1- and 7-acetyl derivatives. The acetyl group of the 3- and 8-acetoxy compounds rearranged into the 2- and 9-positions, respectively. In addition, 1-, 2-, 3-, 4-isopropyl compounds were derived from the corresponding acetyl derivatives.

  4H-环戊二烯基菲-1-基乙酸酯的弗里斯重排得到2-和7-乙酰基衍生物。异构的2-乙酰氧基化合物的反应提供1-和7-乙酰基衍生物。3-和8-乙酰氧基化合物的乙酰基分别重排到2-和9-位。此外，1-、2-、3-、4-异丙基化合物衍生自相应的乙酰基衍生物。
• Aromatic resins for underlayers
  申请人：Rohm and Haas Electronic Materials LLC

  公开号：US10377848B2

  公开（公告）日：2019-08-13

  Polymeric reaction products of certain aromatic alcohols with certain diaryl-substituted aliphatic alcohols are useful as underlayers in semiconductor manufacturing processes.

  某些芳香醇与某些二芳基取代的脂肪醇的聚合物反应产物可用作半导体制造工艺中的底层材料。
• Electrophilic substitution of 4H-cyclopenta[def]phenanthrene. Bromination
  作者：Masaaki Yoshida、Masahiro Minabe、Kazuo Suzuki

  DOI：10.1021/jo01331a014

  日期：1979.8
• YOSHIDA MASAAKI; MINABE MASAHIRO; SUZUKI KAZUO, J. ORG. CHEM., 1979, 44, NO 17, 3029-3031
  作者：YOSHIDA MASAAKI、 MINABE MASAHIRO、 SUZUKI KAZUO

  DOI：——

  日期：——