bis(4-chloro-2-hydroxyphenyl)methanone | 1428245-01-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: bis(4-chloro-2-hydroxyphenyl)methanone
• 英文别名: 4,4'-Dichloro-2,2'-dihydroxy-benzophenone
• CAS: 1428245-01-5
• 化学式: C₁₃H₈Cl₂O₃
• 分子量: 283.111
• InChiKey: RYPGCKUTCBSXAF-UHFFFAOYSA-N

物化性质

• 沸点：
  393.5±42.0 °C(Predicted)
• 密度：
  1.503±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：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  bis(4-chloro-2-hydroxyphenyl)methanone 在 (5aR,10bS)-2-mesityl-5a,10b-dihydro-4H,6H-indeno[2,1-b][1,2,4]triazolo[4,3-d][1,4]oxazin-2-ium tetrafluoroborate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 39.0h， 生成 (M,S)-7-butyl-3,11-dichloro-7,8-dihydro-6H-benzo[2,3]oxocino[5,4-b]benzofuran-6-one
  参考文献：
  名称：

  Diastereo- and Atroposelective Synthesis of Bridged Biaryls Bearing an Eight-Membered Lactone through an Organocatalytic Cascade

  摘要：

  We present herein an unprecedented stereoselective synthesis of bridged biaryls with defined axial and central chirality from readily available starting materials. This N-heterocyclic carbene-catalyzed method proceeds through propargylic substitution of azolium enolates followed by two-directional cyclization, as supported by DFT calculation. A range of benzofuran/indole-derived bridged biaryls bearing an eight-membered lactone are accessed with uniformly high stereoselectivity (>98:2 dr, mostly >98% ee).

  DOI：

  10.1021/jacs.9b08510
• 作为产物：
  描述：

  4,4'-二氯二苯甲酮 在 [RhCl2(p-cymene)]2 、 碘苯二乙酸 、 三氟乙酸 、 三氟乙酸酐 作用下， 以65%的产率得到bis(4-chloro-2-hydroxyphenyl)methanone
  参考文献：
  名称：

  Diastereo- and Atroposelective Synthesis of Bridged Biaryls Bearing an Eight-Membered Lactone through an Organocatalytic Cascade

  摘要：

  We present herein an unprecedented stereoselective synthesis of bridged biaryls with defined axial and central chirality from readily available starting materials. This N-heterocyclic carbene-catalyzed method proceeds through propargylic substitution of azolium enolates followed by two-directional cyclization, as supported by DFT calculation. A range of benzofuran/indole-derived bridged biaryls bearing an eight-membered lactone are accessed with uniformly high stereoselectivity (>98:2 dr, mostly >98% ee).

  DOI：

  10.1021/jacs.9b08510

文献信息

• Broadening the catalyst and reaction scope of regio- and chemoselective C–H oxygenation: a convenient and scalable approach to 2-acylphenols by intriguing Rh(ii) and Ru(ii) catalysis
  作者：Gang Shan、Xuesong Han、Yun Lin、Shanyou Yu、Yu Rao

  DOI：10.1039/c3ob27457h

  日期：——

  catalyzed C–H oxygenation of aryl ketones and other arenes has been developed for the facile synthesis of diverse functionalized phenols. The reaction demonstrates excellent reactivity, regio- and chemoselectivity, good functional group compatibility and high yields. The practicality of this method has been proved by gram-scale synthesis of a few different 2-acylphenols. Its utility has been well exemplified

  已开发出一种独特的Rh（II）和Ru（II）催化的芳基酮和其他芳烃的CH氧化反应，可以轻松合成各种功能化的酚。该反应显示出优异的反应性，区域和化学选择性，良好的官能团相容性和高产率。该方法的实用性已通过克级合成几种不同的2-酰基酚得到了证明。它的效用已在杂环合成和药物的直接修饰中的进一步应用中得到很好的例证非诺贝特。
• Hydroxyl-directed C–C bond activation of benzophenones for the O-acylation of phenols
  作者：Constance B. Anderson、Siri Bruhn、Letitia J. Yao、Christopher J. Douglas

  DOI：10.1016/j.tet.2022.133074

  日期：2022.12

  We report that 2-hydroxyl benzophenones can be converted to phenyl salicylate esters by loss of an aryl group and O-acylation of the phenols. Iridium, cyclooctadiene, and bulky monodentate phosphine ligands catalyze the ketone C–C bond activation and fragmentation. We identified common side products in this process, which include C-acylation of the phenol reactant or trapping on cyclooctadiene. Several

  我们报告说，2-羟基二苯甲酮可以通过失去芳基和苯酚的O-酰化作用转化为水杨酸苯酯。铱、环辛二烯和庞大的单齿膦配体催化酮 C-C 键的活化和断裂。我们确定了该过程中常见的副产物，包括苯酚反应物的C-酰化或环辛二烯的捕获。此处报告的几个过程似乎处于平衡控制之下。总的来说，我们的报告提供了对无应变 C-C 键与第 9 族催化剂的活化和功能化的见解。
• Diastereo- and Atroposelective Synthesis of Bridged Biaryls Bearing an Eight-Membered Lactone through an Organocatalytic Cascade
  作者：Shenci Lu、Jun-Yang Ong、Hui Yang、Si Bei Poh、Xi Liew、Chwee San Deborah Seow、Ming Wah Wong、Yu Zhao

  DOI：10.1021/jacs.9b08510

  日期：2019.10.30

  We present herein an unprecedented stereoselective synthesis of bridged biaryls with defined axial and central chirality from readily available starting materials. This N-heterocyclic carbene-catalyzed method proceeds through propargylic substitution of azolium enolates followed by two-directional cyclization, as supported by DFT calculation. A range of benzofuran/indole-derived bridged biaryls bearing an eight-membered lactone are accessed with uniformly high stereoselectivity (>98:2 dr, mostly >98% ee).