(1R,2R,4S)-2-(6-bromopyridine-2-yl)-1,3,3-trimethylbicyclo[2.2.1]heptan-2-ol | 256428-16-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1R,2R,4S)-2-(6-bromopyridine-2-yl)-1,3,3-trimethylbicyclo[2.2.1]heptan-2-ol
• 英文别名: (1R,2R,4S)-2-(6-bromopyridin-2-yl)-1,3,3-trimethylbicyclo[2.2.1]heptan-2-ol
• CAS: 256428-16-7
• 化学式: C₁₅H₂₀BrNO
• 分子量: 310.234
• InChiKey: DYFZCMYLDMHXJM-VQISRLSMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  33.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1R,2R,4S)-2-(6-bromopyridine-2-yl)-1,3,3-trimethylbicyclo[2.2.1]heptan-2-ol 在 三苯基膦 、 nickel dichloride 、 锌 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以47%的产率得到(1R,2R,4S)-2-[6-[6-[(1R,2R,4S)-2-hydroxy-1,3,3-trimethyl-2-bicyclo[2.2.1]heptanyl]pyridin-2-yl]pyridin-2-yl]-1,3,3-trimethylbicyclo[2.2.1]heptan-2-ol
  参考文献：
  名称：

  New chiral 2,2′-bipyridine diols as catalysts for enantioselective addition of diethylzinc to benzaldehyde

  摘要：

  New C-2-symmetric chiral 2,2'-bipyridine diols were prepared from readily available homochiral materials such as menthone and camphor. Their catalytic activities in the reaction of diethylzinc with benzaldehyde to give 1-phenyl-1-propanol were studied. In all cases, the yields were good and enantioselectivities up to 95% were observed. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00399-7
• 作为产物：
  描述：

  2,6-二溴吡啶 、 (1R)-1,3,3-三甲基二环[2.2.1]庚-2-酮 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以98%的产率得到(1R,2R,4S)-2-(6-bromopyridine-2-yl)-1,3,3-trimethylbicyclo[2.2.1]heptan-2-ol
  参考文献：
  名称：

  Butyllithium-Mediated Coupling of Aryl Bromides with Ketones under In-Situ-Quench (ISQ) Conditions: An Efficient One-Step Protocol Applicable to Microreactor Technology

  摘要：

  利用溴锂交换反应的高反应速率，通过将酮和芳基溴化物的混合物与丁基锂简单结合，可以轻松获得苯丙基醇，例如芬普类配体。

  DOI：

  10.1055/s-2008-1072771

文献信息

• Practical iron-catalyzed dehalogenation of aryl halides
  作者：Waldemar Maximilian Czaplik、Sabine Grupe、Matthias Mayer、Axel Jacobi von Wangelin

  DOI：10.1039/c0cc01980a

  日期：——

  An operationally simple iron-catalyzed hydrodehalogenation of aryl halides has been developed with 1 mol% Fe(acac)3 and commercial t-BuMgCl as reductant. The mild reaction conditions (THF, 0 °C, 1.5 h) effect rapid chemoselective dehalogenation of (hetero)aryl halides (I, Br, Cl) and tolerate F, Cl, OR, SR, CN, CO2R, and vinyl groups.

  开发了一种操作简便的铁催化的芳基卤化物氢脱卤反应，使用1 mol%的Fe(acac)3和商业化的t-BuMgCl作为还原剂。温和的反应条件（THF溶剂，0°C，1.5小时）实现了(杂)芳基卤化物（碘、溴、氯）的快速化学选择性脱卤，并能耐受氟、氯、烷氧基、硫醚、氰基、羧酸酯和乙烯基等官能团。
• Synthesis and Applications of 3-[6-(Hydroxymethyl)pyridin-2-yl]-1,1′-bi-2-naphthols or 3,3′-Bis[6-(hydroxymethyl)pyridin-2-yl]-1,1′-bi-2-naphthols
  作者：Lian-Xun Gao、Li Ma、Rin-Zhe Jin、Guang-Hua Lü、Zhen Bian、Meng-Xian Ding

  DOI：10.1055/s-2007-983787

  日期：2007.8

  A series of new 1,1'-bi-2-naphthol (BINOL) derived ligands, 3-[6-(hydroxymethyl)pyridin-2-yl]-BINOLs or 3,3'-bis[6(hydroxymethyl)pyridin-2-yl]-BINOLs, bearing one or two chiral pyridinylmetlianols attached to a binaphthyl skeleton, have been synthesized using the Suzuki cross-coupling reaction. The resulting compounds have been used as ligands in the enantioselective addition of diethylzinc to aldehydes;

  一系列新的 1,1'-bi-2-naphthol (BINOL) 衍生配体，3-[6-(羟甲基)pyridin-2-yl]-BINOLs 或 3,3'-bis[6(hydroxymethyl)pyridin-已经使用 Suzuki 交叉偶联反应合成了 2-基]-BINOL，其带有一个或两个与联萘骨架相连的手性吡啶基金属醇。所得化合物已用作二乙基锌与醛的对映选择性加成的配体；获得的产品具有高达 96% 的 ee。
• Chiral bipyridine–copper(I) complex-catalyzed enantioselective allylic oxidation of cyclic alkenes
  作者：Wing-Sze Lee、Hoi-Lun Kwong、Hoi-Ling Chan、Wing-Wai Choi、Lai-Yuen Ng

  DOI：10.1016/s0957-4166(01)00160-4

  日期：2001.5

  Chiral copper(I) bipyridine complexes were prepared and used as catalysts in the enantioselective allylic oxidation of cyclic alkenes with tert-butyl perbenzoate. The yields ranged From moderate to good and enantioselectivities up to 70% were observed. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Butyllithium-Mediated Coupling of Aryl Bromides with Ketones under In-Situ-Quench (ISQ) Conditions: An Efficient One-Step Protocol Applicable to Microreactor Technology
  作者：Hans-Günther Schmalz、Sachio Goto、Janna Velder、Sherif El Sheikh、Yuki Sakamoto、Masatoshi Mitani、Said Elmas、Andreas Adler、Anne Becker、Jörg-Martin Neudörfl、Johann Lex

  DOI：10.1055/s-2008-1072771

  日期：2008.5

  Exploiting the high rate of bromine-lithium exchange reactions, aryl carbinols such as fenpy-type ligands are readily obtained by simply combining a mixture of a ketone and an aryl bromide with butyllithium.

  利用溴锂交换反应的高反应速率，通过将酮和芳基溴化物的混合物与丁基锂简单结合，可以轻松获得苯丙基醇，例如芬普类配体。
• New chiral 2,2′-bipyridine diols as catalysts for enantioselective addition of diethylzinc to benzaldehyde
  作者：Hoi-Lun Kwong、Wing-Sze Lee

  DOI：10.1016/s0957-4166(99)00399-7

  日期：1999.9

  New C-2-symmetric chiral 2,2'-bipyridine diols were prepared from readily available homochiral materials such as menthone and camphor. Their catalytic activities in the reaction of diethylzinc with benzaldehyde to give 1-phenyl-1-propanol were studied. In all cases, the yields were good and enantioselectivities up to 95% were observed. (C) 1999 Elsevier Science Ltd. All rights reserved.