(2-((dimethylamino)methyl)phenyl)magnesium bromide | 875221-47-9

• 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: (2-((dimethylamino)methyl)phenyl)magnesium bromide
• CAS: 875221-47-9
• 化学式: C₉H₁₂BrMgN
• 分子量: 238.41
• InChiKey: OPEWWRFXMWBDQH-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  1.39
• 重原子数：
  12.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  3.24
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (2-((dimethylamino)methyl)phenyl)magnesium bromide 在 四丙基高钌酸铵 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 17.0h， 生成 1-(6-bromo-2-methoxyquinolin-3-yl)-1-(2-((dimethylamino)methyl)phenyl)-2-(3-fluorophenyl)ethanol
  参考文献：
  名称：

  Bedaquiline的结构简化：3（4-（N，N-二甲基氨基甲基）苯基）喹啉衍生的抗结核先导化合物的发现

  摘要：

  Bedaquiline（BDQ）是一种新型的高效抗结核药物，已于2013年获得美国FDA批准。由于立体结构的复杂性，化学合成和化合物优化非常困难且昂贵。这项研究描述了苯达喹啉的结构简化，同时保留了抗结核活性。该化合物的结构被分为多个片段，并以各种组合重新组装，同时用非手性键取代了两个手性碳原子。设计了四个系列的类似物。这些候选药物对敏感和耐多药（MDR）结核分枝杆菌均保持其有效的抗结核活性，浓度为每微克每毫升。株。六出前的被发现有9 MIC-排名候选抑制分枝杆菌ATP合成与IC活性50 20和40μ之间的值米，一个有IC 50 > 66μ米，和两个显示无抑制，尽管它们抗结核活性。这些结果为开发化学上不太复杂，成本更低的苯达喹啉衍生物提供了基础，并描述了对非ATP合酶相关靶标具有抗结核活性的两种衍生物的鉴定。

  DOI：

  10.1002/cmdc.201600441
• 作为产物：
  描述：

  bis(2-dimethylaminomethylphenyl)magnesium 以 四氢呋喃 为溶剂， 生成 (2-((dimethylamino)methyl)phenyl)magnesium bromide
  参考文献：
  名称：

  Intramolecularly coordinated arylmagnesium compounds: effects on the Schlenk equilibrium

  摘要：

  A series of phenylmagnesium bromides (1, 3-8) with ortho-substituents capable of forming intramolecular coordinative bonds along with the corresponding diarylmagnesium compounds (1a, 3a-6a, 8a) have been synthesized. The thermodynamic parameters DELTA-H(s) and DELTA-S(s) for the Schlenk equilibria (2 ArMgBr half-arrow-right-over-half-arrow-left Ar2Mg + MgBr2) have been determined by variable temperature NMR spectroscopy. Crystal structures were obtained of 5,6,8,9-tetrahydrodibenz[d,g][1,6]oxamagnescein (2a) and bis(2,6-di(methoxymethyl)phenyl)magnesium (4a). The extent of intramolecular coordination in these compounds as determined in the solid state, is used in the discussion of the influence of substituents on the Schlenk equilibrium parameters. Unusual penta- or hexa-coordination is encountered and explained as a consequence of intramolecular coordination.

  DOI：

  10.1016/0022-328x(91)86244-k

文献信息

• Isolation of Stable Enantiomerically Pure Telluroxides and Their Stereochemistry
  作者：Hideo Taka、Yuko Yamazaki、Toshio Shimizu、Nobumasa Kamigata

  DOI：10.1021/jo991721n

  日期：2000.4.1

  Optical resolution of kinetically and thermodynamically stabilized diaryl telluroxides possessing bulky substituents (rac-1a-d) and amino group (rac-2a-c), respectively, by liquid chromatography using optically active columns yielded stable enantiomerically pure telluroxides. The absolute configurations of the optically active telluroxides were determined by comparing their specific rotations and CD

  通过使用光学活性柱的液相色谱法，分别具有大体积取代基（rac-1a-d）和氨基（rac-2a-c）的动力学和热力学稳定化的二芳基碲化物的光学拆分，得到稳定的对映体纯的碲化物。通过将旋光性碲氧化物的比旋光度和CD光谱与硫或硒类似物的旋光度和CD光谱进行比较，可以确定旋光性碲氧化物的绝对构型。研究了旋光性碲氧化物在溶液中外消旋作用的动力学，发现动力学和热力学稳定作用对于防止碲氧化物的外消旋作用非常有效。通过氨基与碲原子的分子内配位，碲氧化物的稳定能估计为。通过可变温度1H NMR测量得到5kcal mol-1。通过使用H2（18）O的同位素实验研究了旋光性碲化物的消旋作用机理，结果表明旋光性碲化物通过非手性四配位水合物消旋。
• Optical Resolution and Configurational Stability of Selenoxides Stabilized by Intramolecular Coordination
  作者：Toshio Shimizu、Masao Enomoto、Hideo Taka、Nobumasa Kamigata

  DOI：10.1021/jo990993n

  日期：1999.10.1

  rotations, circular dichroism spectra, and behavior on the optically active column with those of the sulfur analogue, prepared by Andersen's method. Racemization of the optically active selenoxides was accelerated not only in acidic solution but also in basic media. This result indicates there are two different mechanisms for their racemization in acidic and basic media. The stabilization energy of the selenoxides

  通过氨基与硒原子分子内配位而构型稳定的2-（（二甲基氨基）甲基）苯基烷基（或芳基）亚硒酸酯通过使用旋光色谱柱的高效液相色谱法光学拆分为对映异构体装满氨基甲酸直链淀粉的衍生物/硅胶。这是分离没有大取代基的光学纯亚硒酸盐的第一个实例，也是光学纯烷基芳基亚硒酸盐的首次分离。（-）-异构体的绝对构型可通过比较它们的比旋光度，圆二色性光谱和在光学活性柱上的行为与由安德森方法制备的硫类似物的行为进行比较，以S形表示。光学活性亚硒酸盐的外消旋不仅在酸性溶液中而且在碱性介质中都被加速。该结果表明它们在酸性和碱性介质中外消旋化有两种不同的机理。通过氨基与硒原子的分子内配位，亚硒酸盐的稳定能估计为约1。3 kcal mol（-）（1），基于可变温度（1）H NMR测量。
• [EN] PROCESS FOR HOMO- OR COPOLYMERIZATIONOF CONJUGATED OLEFINES<br/>[FR] PROCEDE D'HOMO- OU COPOLYMERISATION D'OLEFINES CONJUGUEES
  申请人：DOW GLOBAL TECHNOLOGIES INC

  公开号：WO2004074333A2

  公开（公告）日：2004-09-02

  Metal complexes suitable for use in polymerization are described which correspond to Formula (1) in which M is yttrium, a group 4 metal, a lanthanide or an actinide metal; Ml is a group 1 or group 2 metal; T independently each occurrence is nitrogen or phosphorus; RB and RC independently each occurrence is hydrogen or is selected from certain groups and two RC groups may be joined together forming a divalent ligand group; X independently each occurrence is an anionic ligand group having up to 60 atoms, provided that X is not a cyclic, delocalized, aromatic group that is π-bonded to M, and two X groups together may form a divalent ligand group; D independently each occurrence is a neutral Lewis base ligand having up to 30 nonhydrogen atoms; x is the number 1, 2 or 3; x' is the number 1 or 2; t is a number from 0 to 3; t' is a number from 0 to 3; r is the number 0 or 1 and o is the number 1 or 2. These metal complexes may be combined with one or more activator compounds to make catalyst compositions which may be used to manufacture polymers having a high percentage of the fraction of residual olefinic double bonds that are Z or cis units and a, low 1,2 polybutadiene content. The polymers are useful for modification of plastics and for the manufacture of a wide range of products including tires, golf balls, hoses, belts, gaskets, seals, and shoes.
• Structural Simplification of Bedaquiline: the Discovery of 3-(4-(<i>N</i>,<i>N</i>-Dimethylaminomethyl)phenyl)quinoline-Derived Antitubercular Lead Compounds
  作者：Chunxian He、Laura Preiss、Bin Wang、Lei Fu、Hui Wen、Xiang Zhang、Huaqing Cui、Thomas Meier、Dali Yin

  DOI：10.1002/cmdc.201600441

  日期：2017.1.20

  their potent antitubercular activity at sub‐microgram per mL concentrations against both sensitive and multidrug‐resistant (MDR) Mycobacterium tuberculosis strains. Six out of the top nine MIC‐ranked candidates were found to inhibit mycobacterial ATP synthesis activity with IC50 values between 20 and 40 μm, one had IC50>66 μm, and two showed no inhibition, despite their antitubercular activity. These results

  Bedaquiline（BDQ）是一种新型的高效抗结核药物，已于2013年获得美国FDA批准。由于立体结构的复杂性，化学合成和化合物优化非常困难且昂贵。这项研究描述了苯达喹啉的结构简化，同时保留了抗结核活性。该化合物的结构被分为多个片段，并以各种组合重新组装，同时用非手性键取代了两个手性碳原子。设计了四个系列的类似物。这些候选药物对敏感和耐多药（MDR）结核分枝杆菌均保持其有效的抗结核活性，浓度为每微克每毫升。株。六出前的被发现有9 MIC-排名候选抑制分枝杆菌ATP合成与IC活性50 20和40μ之间的值米，一个有IC 50 > 66μ米，和两个显示无抑制，尽管它们抗结核活性。这些结果为开发化学上不太复杂，成本更低的苯达喹啉衍生物提供了基础，并描述了对非ATP合酶相关靶标具有抗结核活性的两种衍生物的鉴定。
• Intramolecularly coordinated arylmagnesium compounds: effects on the Schlenk equilibrium
  作者：Peter R. Markies、Rinke M. Altink、Alan Villena、Otto S. Akkerman、Friedrick Bickelhaupt、Wilberth J.J. Smeets、Anthony L. Spek

  DOI：10.1016/0022-328x(91)86244-k

  日期：1991.1

  A series of phenylmagnesium bromides (1, 3-8) with ortho-substituents capable of forming intramolecular coordinative bonds along with the corresponding diarylmagnesium compounds (1a, 3a-6a, 8a) have been synthesized. The thermodynamic parameters DELTA-H(s) and DELTA-S(s) for the Schlenk equilibria (2 ArMgBr half-arrow-right-over-half-arrow-left Ar2Mg + MgBr2) have been determined by variable temperature NMR spectroscopy. Crystal structures were obtained of 5,6,8,9-tetrahydrodibenz[d,g][1,6]oxamagnescein (2a) and bis(2,6-di(methoxymethyl)phenyl)magnesium (4a). The extent of intramolecular coordination in these compounds as determined in the solid state, is used in the discussion of the influence of substituents on the Schlenk equilibrium parameters. Unusual penta- or hexa-coordination is encountered and explained as a consequence of intramolecular coordination.