9-(1-hydroxy-1-methylethyl)anthracene | 66398-74-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 9-(1-hydroxy-1-methylethyl)anthracene
• 英文别名: 9-(2-Hydroxy-2-propyl)anthracene；2-(9-anthryl)-2-propanol；9-(α-Hydroxy-isopropyl)-anthracen；2-Anthracen-9-ylpropan-2-ol
• CAS: 66398-74-1
• 化学式: C₁₇H₁₆O
• 分子量: 236.313
• InChiKey: YIMCIGZNCKTKJW-UHFFFAOYSA-N

物化性质

• 熔点：
  132-134 °C(Solv: benzene (71-43-2))
• 沸点：
  424.9±14.0 °C(Predicted)
• 密度：
  1.150±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  9-(1-hydroxy-1-methylethyl)anthracene 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 2-[9-(2-Hydroxypropan-2-yl)-1-heptacyclo[8.6.6.62,9.03,8.011,16.017,22.023,28]octacosa-3,5,7,11,13,15,17,19,21,23,25,27-dodecaenyl]propan-2-ol
  参考文献：
  名称：

  Photochemical dimerization modes of 9-methoxyanthracenes and 9-(2-hydroxy-2-propyl)anthracene

  摘要：

  Irradiation of 9-methoxyanthracene in ether solution at room temperature gives, in a ratio of about 55:45, head-to-tail and head-to-head substituted dianthracenes, which have been isolated by colum chromatography on silica gel. Photochemical dimerization of 9-methoxy-10-methylanthracene afforded the known centrosymmetrical 4pi + 4pi cycloaddition product. By contrast, photoexcitation of 9-methoxy-10-methylanthracene in the presence of 9-methoxyanthracene results mainly in the formation of the two possible heterodimers by 4pi + 4pi cycloaddition. Photochemical head-to-tail dimerization of 9-(2-hydroxy-2-propyl)anthracene gives two diastereomeric dianthracenes which, due to their rotationally blocked 2-hydroxy-2-propyl substituents, are characterized by i- and C2-symmetry, respectively. Deviations from planarity of the aromatic pi-system in crystalline 9-methoxy-, 9-methoxy-10-methyl-, and 9-(2-hydroxy-2-propyl)anthracene, and the effects of substituents on the molecular topology of various dianthracenes, have been evaluated by X-ray diffraction.

  DOI：

  10.1021/jo00069a038
• 作为产物：
  描述：

  9-溴蒽 、 丙酮 在 正丁基锂 作用下， 以 乙醚 为溶剂， 以40%的产率得到9-(1-hydroxy-1-methylethyl)anthracene
  参考文献：
  名称：

  Photochemical dimerization modes of 9-methoxyanthracenes and 9-(2-hydroxy-2-propyl)anthracene

  摘要：

  Irradiation of 9-methoxyanthracene in ether solution at room temperature gives, in a ratio of about 55:45, head-to-tail and head-to-head substituted dianthracenes, which have been isolated by colum chromatography on silica gel. Photochemical dimerization of 9-methoxy-10-methylanthracene afforded the known centrosymmetrical 4pi + 4pi cycloaddition product. By contrast, photoexcitation of 9-methoxy-10-methylanthracene in the presence of 9-methoxyanthracene results mainly in the formation of the two possible heterodimers by 4pi + 4pi cycloaddition. Photochemical head-to-tail dimerization of 9-(2-hydroxy-2-propyl)anthracene gives two diastereomeric dianthracenes which, due to their rotationally blocked 2-hydroxy-2-propyl substituents, are characterized by i- and C2-symmetry, respectively. Deviations from planarity of the aromatic pi-system in crystalline 9-methoxy-, 9-methoxy-10-methyl-, and 9-(2-hydroxy-2-propyl)anthracene, and the effects of substituents on the molecular topology of various dianthracenes, have been evaluated by X-ray diffraction.

  DOI：

  10.1021/jo00069a038

文献信息

• Palladium-Catalyzed Arylation of α,α-Disubstituted Arylmethanols via Cleavage of a C−C or a C−H Bond To Give Biaryls
  作者：Yoshito Terao、Hiroyuki Wakui、Michiyo Nomoto、Tetsuya Satoh、Masahiro Miura、Masakatsu Nomura

  DOI：10.1021/jo0344034

  日期：2003.6.1

  The palladium-catalyzed arylation of alpha,alpha-disubstituted arylmethanols with aryl halides proceeds not only via C-H bond cleavage at the ortho-position, but also via cleavage of the sp(2)-sp(3) C-C bond with the liberation of ketones (beta-carbon elimination) to give the corresponding biaryls. Both reactions appear to occur through common arylpalladium(II) alcoholate intermediates. The results

  钯催化的α，α-二取代的芳基甲醇与芳基卤化物的芳基化反应不仅通过邻位的CH键裂解，还通过sp（2）-sp（3）CC键的裂解以及酮的释放而进行（β-碳消除）得到相应的联芳基。这两个反应似乎都是通过常见的芳基钯（II）醇盐中间体发生的。报道了关于在芳基化中优先裂解CC或CH键的系统研究的结果。在重要发现中，由于空间原因，甚至可以从芳基（二苯基）甲醇中选择性除去邻位取代的芳基。因此，通过用芳基溴化物和氯化物处理相应的芳基（二苯基或二甲基）甲醇，可以有效地生产具有邻取代基的各种联芳基。
• Characterization of an RNA Active Site:  Interactions between a Diels−Alderase Ribozyme and Its Substrates and Products
  作者：Friedrich Stuhlmann、Andres Jäschke

  DOI：10.1021/ja0167405

  日期：2002.4.1

  substrates and accelerates cycloadditions with both enantio- and diastereoselectivity. The stereochemistry of the reaction is controlled by RNA-diene interactions. The RNA interacts strongly and stereoselectively with the cycloaddition products, requiring several structural features to be present. Taken together, the results highlight the intricacy of ribozyme active sites which can control chemical reaction

  最近已显示核酶催化小有机分子之间碳-碳键的立体选择性形成。这些 Diels-Alderase 核酶与其底物和产物的相互作用现已通过使用 44 种不同的、系统变化的类似物的化学取代分析得到阐明。RNA-二烯相互作用受堆叠相互作用控制，而氢键和金属离子配位似乎不太重要。二烯必须是蒽衍生物，并且允许在指定位置上有取代基，从而揭示结合位点的几何形状。亲二烯体必须是具有未取代反应性双键的五元马来酰亚胺环，疏水侧链对 RNA 结合有重要贡献。核酶区分手性底物的不同对映异构体，并以对映选择性和非对映选择性加速环加成。反应的立体化学由 RNA-二烯相互作用控制。RNA 与环加成产物强烈且立体选择性地相互作用，需要存在几个结构特征。总之，结果突出了核酶活性位点的复杂性，它可以根据底物立体化学和取代模式的微小差异控制化学反应途径。需要存在几个结构特征。总之，结果突出了核酶活性位点的复杂性，它可以根据底物立体化
• Unusual Inhibition Effect of 1-(1-Naphthyl)-1-methylethylhydroperoxide on the Liquid-Phase Oxidation of Isopropylarenes. GC−MS and Theoretical Studies of the Thermal Decomposition of 1-Naphthyl- and 1-Anthryl-1-methylethylhydroperoxides
  作者：Roman Mazurkiewicz、Jan Zawadiak、Beata Orlińska、Barbara Hefczyc、Zbigniew Stec、Mirosława Grymel、Piotr Fiedorow、Henryk Koroniak

  DOI：10.1021/op0502351

  日期：2006.3.1

  have thus far never been described as thermal decomposition products of 1-aryl-1-methylethylhydroperoxides. The plausible mechanism of the formation of 2-(1-aryloxy)propenes was proposed on the basis of AM-1 calculations of the possible rearrangement paths of the alkoxy radicals derived from the investigated hydroperoxides. The mechanism explains the inhibition effect of 1-(1-naphthyl)-1-methylethylhydroperoxide

  合成了由萘和蒽衍生的所有五种可能的1-芳基-1甲基乙基氢过氧化物，并研究了它们在GC-MS条件下的热分解，以解释1-（1-萘基）-1-甲基乙基氢过氧化物对液相氧化的异常抑制作用异丙基芳烃。2-（1-芳氧基）丙烯被鉴定为1-（1-萘基）-1-甲基乙基氢过氧化物和1-（1-蒽基）-1-甲基乙基氢过氧化物的主要分解产物。迄今为止，从未将相对不稳定的2-芳基氧基丙烯描述为1-芳基-1-甲基乙基氢过氧化物的热分解产物。根据AM-1计算得出了2-（1-芳氧基）丙烯形成的合理机理，该AM-1计算源自研究过的氢过氧化物的烷氧基的可能重排路径。
• Restricted Rotation Involving the Tetrahedral Carbon. XLIV. Atropisomers of 2,3-Dichloro-9-(1-hydroxy-1-methylethyl)triptycene and Related Compounds
  作者：Michinori Oki、Yoshiyuki Tanaka、Gaku Yamamoto、Nobuo Nakamura

  DOI：10.1246/bcsj.56.302

  日期：1983.1

  Atropisomers of 2,3-dichloro-9-(1-hydroxy-1-methylethyl)triptycene were obtained as stable compounds at room temperature. The barrier to rotation (±sc→ap) was 34.0 kcal/mol at 153 °C. Other 9-(1-hydroxy-1-methylethyl)triptycenes carrying a substituent in the 1-position of the skeleton gave ±sc isomers only. Attempted isomerization of the ±sc forms failed because the free energy difference between the

  2,3-二氯-9-(1-羟基-1-甲基乙基)triptycene 的阻转异构体在室温下作为稳定化合物获得。在 153 °C 时，旋转障碍 (±sc→ap) 为 34.0 kcal/mol。其他在骨架的 1-位带有取代基的 9-(1-羟基-1-甲基乙基)三烯仅产生±sc 异构体。±sc 形式的异构化尝试失败，因为由于空间效应，±sc 和 ap 形式之间的自由能差异很大。制备±sc-9-(1-Methoxy-1-methylethyl)-1,4-二甲基三苯，希望增加羟基的空间尺寸将有助于在加热时产生α-异构体。检测到 ap 异构体，但总体比率 ap⁄±sc 太小而无法分离 ap。
• OKI, MICHINORI;TANAKA, YOSHIYUKI;YAMAMOTO, GAKU;NAKAMURA, NOBUO, BULL. CHEM. SOC. JAP., 1983, 56, N 1, 302-305
  作者：OKI, MICHINORI、TANAKA, YOSHIYUKI、YAMAMOTO, GAKU、NAKAMURA, NOBUO

  DOI：——

  日期：——