(1R,4R)-2-(6-bromopyridin-2-yl)-1,7,7-trimethylbicyclo[2.2.1]-2-heptene | 253783-09-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: (1R,4R)-2-(6-bromopyridin-2-yl)-1,7,7-trimethylbicyclo[2.2.1]-2-heptene
• 英文别名: 2-bromo-6-[(1R,4R)-1,7,7-trimethylbicyclo[2.2.1]hept-2-en-2-yl]pyridine；2-bromo-6-[(1R,4R)-1,7,7-trimethylbicyclo[2.2.1]hept-2-en-2-yl]-pyridine；2-bromo-6-[(1R,4R)-1,7,7-trimethyl-2-bicyclo[2.2.1]hept-2-enyl]pyridine
• CAS: 253783-09-4
• 化学式: C₁₅H₁₈BrN
• 分子量: 292.219
• InChiKey: RILUNZOOKBZSQU-BMIGLBTASA-N

物化性质

• 沸点：
  351.6±30.0 °C(Predicted)
• 密度：
  1.308±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 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,4R)-2-(6-bromopyridin-2-yl)-1,7,7-trimethylbicyclo[2.2.1]-2-heptene 在 四(三苯基膦)钯 potassium tert-butylate 、 水 、 sodium carbonate 作用下， 以 甲醇 、 二甲基亚砜 、 甲苯 为溶剂， 反应 31.0h， 生成 2-[(1S,2S,3R,4S)-3-(diphenylphosphoryl)-1,7,7-trimethylbicyclo[2.2.1]hept-2-yl]-6-phenylpyridine
  参考文献：
  名称：

  t-BuOK-Mediated Hydrophosphination of Functionalized Alkenes:  A Novel Synthesis of Chiral P,N- and P,P-Ligands

  摘要：

  A novel synthesis of effective chiral P,N- and P,P-ligands has been developed by using a t-BuOK-mediated hydrophosphination of chiral alkenylpyridines and alkenylphosphine oxides. Ir complexes of chiral P,N-ligrands 1 and 3 gave high enantioselectivities for the hydrogenation of (Z)-alpha(acetamido)cinnamate 25 and (E)-1,2-diphenylpropene leading to the hydrogenated products with up to 97% ee.

  DOI：

  10.1021/jo030383u
• 作为产物：
  描述：

  (1R,2R,4R)-2-(6-bromopyridin-2-yl)-1,7,7-trimethylbicyclo-[2.2.1]heptan-2-ol 在 吡啶 、 氯化亚砜 作用下， 反应 1.5h， 生成 (1R,4R)-2-(6-bromopyridin-2-yl)-1,7,7-trimethylbicyclo[2.2.1]-2-heptene
  参考文献：
  名称：

  Enantiomerically pure pyridine and 2,2′-bipyridine thioethers: new N–S chiral ligands for asymmetric catalysis. Palladium-catalyzed allylic alkylation

  摘要：

  Diastereomeric pure pyridine and 2,2'-bipyridine thioethers, derived from (+)-camphor, were prepared and assessed in the enantioselective palladium-catalyzed allylic substitution of 1,3-diphenylprop-2-enyl acetate with dimethyl malonate. Enantioselectivities of up to 76% were obtained. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00352-3

文献信息

• Chiral ligands and their transition metal complexes
  申请人：Scholz Ulrich

  公开号：US20070066825A1

  公开（公告）日：2007-03-22

  The present invention relates to chiral phosphorus compounds and their transition metal complexes, and also to the use of these transition metal complexes, especially in asymmetric syntheses.

  本发明涉及手性磷化合物及其过渡金属配合物，以及这些过渡金属配合物的应用，特别是在不对称合成中的应用。
• New P,N Ligands for Asymmetric Ir-Catalyzed Reactions
  作者：Tanasri Bunlaksananusorn、Kurt Polborn、Paul Knochel

  DOI：10.1002/anie.200351936

  日期：2003.8.25
• [DE] CHIRALE LIGANDEN UND DEREN ÜBERGANGSMETALLKOMPLEXE<br/>[EN] CHIRAL LIGANDS AND THEIR TRANSITION METAL COMPLEXES<br/>[FR] LIGANDS CHIRAUX ET LEURS COMPLEXES DE METAUX DE TRANSITION
  申请人：BAYER CHEMICALS AG

  公开号：WO2004104014A3

  公开（公告）日：2005-03-17
• <i>t</i>-BuOK-Mediated Hydrophosphination of Functionalized Alkenes:  A Novel Synthesis of Chiral P,N- and P,P-Ligands
  作者：Tanasri Bunlaksananusorn、Paul Knochel

  DOI：10.1021/jo030383u

  日期：2004.7.1

  A novel synthesis of effective chiral P,N- and P,P-ligands has been developed by using a t-BuOK-mediated hydrophosphination of chiral alkenylpyridines and alkenylphosphine oxides. Ir complexes of chiral P,N-ligrands 1 and 3 gave high enantioselectivities for the hydrogenation of (Z)-alpha(acetamido)cinnamate 25 and (E)-1,2-diphenylpropene leading to the hydrogenated products with up to 97% ee.
• Enantiomerically pure pyridine and 2,2′-bipyridine thioethers: new N–S chiral ligands for asymmetric catalysis. Palladium-catalyzed allylic alkylation
  作者：Giorgio Chelucci、Nicola Culeddu、Antonio Saba、Raffaela Valenti

  DOI：10.1016/s0957-4166(99)00352-3

  日期：1999.9

  Diastereomeric pure pyridine and 2,2'-bipyridine thioethers, derived from (+)-camphor, were prepared and assessed in the enantioselective palladium-catalyzed allylic substitution of 1,3-diphenylprop-2-enyl acetate with dimethyl malonate. Enantioselectivities of up to 76% were obtained. (C) 1999 Elsevier Science Ltd. All rights reserved.