tert-butyl 3-phenanthryl ketone | 856979-35-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: tert-butyl 3-phenanthryl ketone
• 英文别名: 2,2-dimethyl-1-[3]phenanthryl-propan-1-one；2,2-Dimethyl-1-[3]phenanthryl-propan-1-on；2,2-Dimethyl-1-phenanthren-3-ylpropan-1-one；2,2-dimethyl-1-phenanthren-3-ylpropan-1-one
• CAS: 856979-35-6
• 化学式: C₁₉H₁₈O
• 分子量: 262.351
• InChiKey: YOMPFARRXIHTFT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  tert-butyl 3-phenanthryl ketone 在 三乙基硅烷 、 正丁基锂 、 三氟乙酸 作用下， 以 乙醚 、 正己烷 、 二氯甲烷 为溶剂， 生成 2-[2-(4,4-dimethyl-3-phenanthren-3-yl-pent-1-ynyl)-phenylethynyl]-2'-methoxy-[1,1']binaphthalenyl
  参考文献：
  名称：

  Synthesis and separation of the atropisomers of 2-(5-benzo[b]fluorenyl)-2′-hydroxy-1,1′-binaphthyl and related compounds

  摘要：

  Several syn and anti atropisomers of 2-(5-benzo[b]fluorenyl)-2'-hydroxy-1,1'-binaphthyl and related compounds were synthesized from 1,1'-binaphthyl-2,2'-diol (BINOL). It was possible to separate the syn and anti atropisomers by silica gel column chromatography. The syn atropisomers are potential hetero-bidentate ligands for complex formation with metals. By starting from enantiomerically pure (R)-(+)-BINOL and (S)-(-)-BINOL, four optically active syn atropisomers and two anti atropisomers with high enantiomeric purity were obtained. The structures of two syn atropisomers and one anti atropisomer were established by X-ray structure analyses. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.06.004
• 作为产物：
  描述：

  3-菲甲酸 在 氯化亚砜 作用下， 生成 tert-butyl 3-phenanthryl ketone
  参考文献：
  名称：

  Synthesis and separation of the atropisomers of 2-(5-benzo[b]fluorenyl)-2′-hydroxy-1,1′-binaphthyl and related compounds

  摘要：

  Several syn and anti atropisomers of 2-(5-benzo[b]fluorenyl)-2'-hydroxy-1,1'-binaphthyl and related compounds were synthesized from 1,1'-binaphthyl-2,2'-diol (BINOL). It was possible to separate the syn and anti atropisomers by silica gel column chromatography. The syn atropisomers are potential hetero-bidentate ligands for complex formation with metals. By starting from enantiomerically pure (R)-(+)-BINOL and (S)-(-)-BINOL, four optically active syn atropisomers and two anti atropisomers with high enantiomeric purity were obtained. The structures of two syn atropisomers and one anti atropisomer were established by X-ray structure analyses. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.06.004

文献信息

• Synthesis and structures of helical polycyclic aromatic hydrocarbons bearing aryl substituents at the most sterically hindered positions
  作者：Yanzhong Zhang、Jeffrey L. Petersen、Kung K. Wang

  DOI：10.1016/j.tet.2007.11.073

  日期：2008.2

  polycyclic aromatic hydrocarbons bearing one or two aryl substituents at the most sterically hindered positions to cause helical twists. The dynamic behaviors involving the helix inversion and the restricted rotation of the aryl substituents were investigated by temperature-dependent NMR studies. The X-ray structure of an indeno-fused 1-phenylpentahelicene derivative showed severe distortion of the [5]helicene

  建立了一个三步合成序列，从苯甲二烯二炔与芳基叔丁基酮之间的缩合反应开始，以使人们容易接近在最受阻位上带有一个或两个芳基取代基的有角稠合多环芳烃，从而引起螺旋扭曲。通过依赖于温度的NMR研究来研究涉及螺旋反转和芳基取代基的受限旋转的动力学行为。茚并稠合的1-苯基戊烯衍生物的X射线结构显示，[5]螺旋系统因平面度而严重变形。
• Synthesis and separation of the atropisomers of 2-(5-benzo[b]fluorenyl)-2′-hydroxy-1,1′-binaphthyl and related compounds
  作者：Hua Yang、Jeffrey L. Petersen、Kung K. Wang

  DOI：10.1016/j.tet.2006.06.004

  日期：2006.8

  Several syn and anti atropisomers of 2-(5-benzo[b]fluorenyl)-2'-hydroxy-1,1'-binaphthyl and related compounds were synthesized from 1,1'-binaphthyl-2,2'-diol (BINOL). It was possible to separate the syn and anti atropisomers by silica gel column chromatography. The syn atropisomers are potential hetero-bidentate ligands for complex formation with metals. By starting from enantiomerically pure (R)-(+)-BINOL and (S)-(-)-BINOL, four optically active syn atropisomers and two anti atropisomers with high enantiomeric purity were obtained. The structures of two syn atropisomers and one anti atropisomer were established by X-ray structure analyses. (c) 2006 Elsevier Ltd. All rights reserved.