(-)-(1R,5R)-2,3-(2'-Phenyl-1'-azobenzo)-6,6-dimethylbicyclo[3.1.1]heptane | 173787-59-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: (-)-(1R,5R)-2,3-(2'-Phenyl-1'-azobenzo)-6,6-dimethylbicyclo[3.1.1]heptane
• 英文别名: (1R,9R)-10,10-dimethyl-5-phenyl-6-azatricyclo[7.1.1.02,7]undeca-2(7),3,5-triene
• CAS: 173787-59-2
• 化学式: C₁₈H₁₉N
• 分子量: 249.356
• InChiKey: WBFZWKQAWCRJBL-HIFRSBDPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (-)-(1R,5R)-2,3-(2'-Phenyl-1'-azobenzo)-6,6-dimethylbicyclo[3.1.1]heptane 在 过氧乙酸 、 sodium hydroxide 作用下， 以 甲醇 、 溶剂黄146 为溶剂， 反应 33.0h， 生成 (1R,8R,9S)-10,10-Dimethyl-5-phenyl-6-aza-tricyclo[7.1.1.0^2,7]undeca-2(7),3,5-trien-8-ol
  参考文献：
  名称：

  合成新的手性催化剂，取代的2-苯基-5,6,7,8-四氢-6,6-二甲基-5,7-甲氧基喹啉，用于将二乙基锌对苯甲醛对映选择性加成

  摘要：

  制备了新的手性配体，即取代的2-苯基-5,6,7,8-四氢-6,6-二甲基-5,7-甲基-喹啉，并在各种条件下研究了二乙基锌与苯甲醛的催化反应，得到了1-苯基-1-丙醇，ee最高至91％。

  DOI：

  10.1016/0957-4166(95)00381-9
• 作为产物：
  描述：

  pinocarvone 、 N-苯甲酰甲基溴吡啶 在 ammonium acetate 作用下， 以 溶剂黄146 为溶剂， 反应 20.0h， 以60%的产率得到(-)-(1R,5R)-2,3-(2'-Phenyl-1'-azobenzo)-6,6-dimethylbicyclo[3.1.1]heptane
  参考文献：
  名称：

  合成新的手性催化剂，取代的2-苯基-5,6,7,8-四氢-6,6-二甲基-5,7-甲氧基喹啉，用于将二乙基锌对苯甲醛对映选择性加成

  摘要：

  制备了新的手性配体，即取代的2-苯基-5,6,7,8-四氢-6,6-二甲基-5,7-甲基-喹啉，并在各种条件下研究了二乙基锌与苯甲醛的催化反应，得到了1-苯基-1-丙醇，ee最高至91％。

  DOI：

  10.1016/0957-4166(95)00381-9

文献信息

• The epimerization of chiral half sandwich 2-phenylpyridine-based ruthenacycle
  作者：Jean-Pierre Djukic、Manon Duquenne、Alexsandro Berger、Michel Pfeffer

  DOI：10.1016/j.ica.2005.06.026

  日期：2006.4

  The reaction of a chiral terpenic 2-phenylpyridine with mercury (11) acetate afforded a new ortho-chloromercurated substrate, which was treated with [(eta(6)-cymene)RuCl2](2) to afford two diastereomers of the corresponding half-sandwich cyclochlororuthenated terpenic ligand. The latter two complexes were successfully separated by conventional chromatography and their configurational stability investigated by H-1 NMR and CD spectroscopy. It was found that both isolated diastereomers displayed a fair configurational stability in CH2Cl2 while when dissolved in MeOH they epimerize. It was shown that the rate of epimerization is rather slow in pure MeOH, whereas in the presence of an excess of Lewis acid such as HgCl2 it was notably accelerated suggesting that the decoordination of the chloride from the Ru(II) center is a key step in the epimerization process. (c) 2005 Elsevier B.V. All rights reserved.
• Asymmetric hydrogenation and allylic substitution reaction with novel chiral pinene-derived N,P-ligands
  作者：Xiangyan Meng、Xinsheng Li、Dongcheng Xu

  DOI：10.1016/j.tetasy.2009.05.020

  日期：2009.7

  A series of new chiral tetrahydroquinoline ligands, derived from chiral alpha-pinene, were successfully synthesized. Iridium and palladium complexes of these ligands were proven to be efficient catalysts for enantioselective hydrogenation and allylic substitution reactions with moderate to excellent enantioselectivities (90-95% ee) and high yields. (C) 2009 Elsevier Ltd. All rights reserved.
• Enantioselective palladium catalyzed allylic substitution with sulfur-containing pyridine ligands
  作者：Giorgio Chelucci、M. Antonietta Cabras

  DOI：10.1016/0957-4166(96)00092-4

  日期：1996.4

  Diastereomerically pure (5R,7R,8S)- and (5R,7R,8R)-5,6,7,8-tetrahydro-6, 6-dimethyl-2-phenyl-8-phenyltio-5,7-methanoquinoline were prepared and assessed in the enantioselective palladium catalyzed allylic substitution of 1,3-diphenylprop-2-enyl acetate with dimethylmalonate. Enantioselectivities up to 83% were obtained. Copyright (C) 1996 Elsevier Science Ltd
• Synthesis of new chiral catalysts, pyridyl- and bipyridylalcohols, for the enantioselective addition of diethylzinc to benzaldehyde
  作者：Philippe Collomb、Alex von Zelewsky

  DOI：10.1016/s0957-4166(98)00399-1

  日期：1998.11

  New chiral ligands, pyridyl- and bipyridylalcohols, were prepared and their catalytic role in the reaction of diethylzinc with benzaldehyde to give 1-phenyl-1-propanol was studied. In several cases, the yields approach 100%, and ee-values of up to 86% are observed. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Stereoselective synthesis of cyclometalated iridium(III) complexes: Characterization and photophysical properties
  作者：Liangru Yang、Alex von Zelewsky、Huong P. Nguyen、Gilles Muller、Gaël Labat、Helen Stoeckli-Evans

  DOI：10.1016/j.ica.2008.10.011

  日期：2009.8

  The stereoselective synthesis of a highly luminescent neutral Ir(III) complex comprising two bidentate chiral, cyclometalating phenylpyridine derivatives, and one acetylacetonate as ligands is described. The final complex and some intermediates were characterized by X-ray structural analysis, NMR-, CD-, and CPL-spectroscopy. (C) 2008 Published by Elsevier B.V.