3-Methyl-4-(4-methylbenzyloxy)phenylboronic acid | 309947-08-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-Methyl-4-(4-methylbenzyloxy)phenylboronic acid
• 英文别名: [3-Methyl-4-[(4-methylphenyl)methoxy]phenyl]boronic acid
• CAS: 309947-08-8
• 化学式: C₁₅H₁₇BO₃
• 分子量: 256.109
• InChiKey: DFBXNEZQVHOIPJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.56
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-Methyl-4-(4-methylbenzyloxy)phenylboronic acid 在 四(三苯基膦)钯 水 、 4-甲基苯磺酸吡啶 、 碳酸氢钠 作用下， 以 甲醇 、 乙二醇二甲醚 为溶剂， 反应 9.0h， 生成 3-[3,3'-Dimethyl-4'-(4-methylbenzyl)biphenyl-4-yloxy]propane-1,2-diol
  参考文献：
  名称：

  Thermotropic and Lyotropic Liquid Crystalline Phases of Rigid Aromatic Amphiphiles

  摘要：

  Rodlike amphiphilic molecules that contain exclusively aromatic building-blocks and no flexible alkyl chains have been synthesized and their mesomorphic properties investigated. These novel compounds bear diol head groups of different size (2,3-dihydroxypropyloxy or 5,6-dihydroxy-3-oxahexyloxy groups) at one end of a biphenyl unit, various aromatic segments (banzyloxy, 4-, 3-, or 2-methylbenzyloxy, phenoxy groups) at the other, and additional methyl substituents in different positions. They were synthesized by using Suzuki cross-coupling reactions as the key steps. Their thermotropic mesomorphism was investigated by means of polarized light optical microscopy, differential scanning calorimetry, and, for enantiotropic phases, by X-ray scattering. The liquid crystallinity of this class of compounds is influenced by protic solvents, such as water and glycerol. Dependent on the temperature and the solvent content, different S-A phases were found. Several mesophases resulting from the frustration of these layer structures (e.g., different columnar phases, optical isotropic mesophases, and nematic phases) were also present. The smectic phases have different degrees of intercalation (S-Ad, S-A2) The columnar phases are supposed to be ribbon structures that result from the collapse of the smectic layers. They occur in some pure compounds or they are induced upon the addition of protic solvents. The particular phase sequences of the different compounds depend mainly on the position of the methyl substituents at the biphenyl cores and are largely determined by the degree of intercalation of the aromatic cores.

  DOI：

  10.1002/1521-3765(20001016)6:20<3821::aid-chem3821>3.0.co;2-8
• 作为产物：
  描述：

  4-Bromo-2-methyl-1-(4-methylbenzyloxy)benzene 在 盐酸 、 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 3.0h， 生成 3-Methyl-4-(4-methylbenzyloxy)phenylboronic acid
  参考文献：
  名称：

  Thermotropic and Lyotropic Liquid Crystalline Phases of Rigid Aromatic Amphiphiles

  摘要：

  Rodlike amphiphilic molecules that contain exclusively aromatic building-blocks and no flexible alkyl chains have been synthesized and their mesomorphic properties investigated. These novel compounds bear diol head groups of different size (2,3-dihydroxypropyloxy or 5,6-dihydroxy-3-oxahexyloxy groups) at one end of a biphenyl unit, various aromatic segments (banzyloxy, 4-, 3-, or 2-methylbenzyloxy, phenoxy groups) at the other, and additional methyl substituents in different positions. They were synthesized by using Suzuki cross-coupling reactions as the key steps. Their thermotropic mesomorphism was investigated by means of polarized light optical microscopy, differential scanning calorimetry, and, for enantiotropic phases, by X-ray scattering. The liquid crystallinity of this class of compounds is influenced by protic solvents, such as water and glycerol. Dependent on the temperature and the solvent content, different S-A phases were found. Several mesophases resulting from the frustration of these layer structures (e.g., different columnar phases, optical isotropic mesophases, and nematic phases) were also present. The smectic phases have different degrees of intercalation (S-Ad, S-A2) The columnar phases are supposed to be ribbon structures that result from the collapse of the smectic layers. They occur in some pure compounds or they are induced upon the addition of protic solvents. The particular phase sequences of the different compounds depend mainly on the position of the methyl substituents at the biphenyl cores and are largely determined by the degree of intercalation of the aromatic cores.

  DOI：

  10.1002/1521-3765(20001016)6:20<3821::aid-chem3821>3.0.co;2-8

文献信息

• Thermotropic and Lyotropic Liquid Crystalline Phases of Rigid Aromatic Amphiphiles
  作者：Marius Kölbel、Tom Beyersdorff、Carsten Tschierske、Siegmar Diele、Jens Kain

  DOI：10.1002/1521-3765(20001016)6:20<3821::aid-chem3821>3.0.co;2-8

  日期：2000.10.16

  Rodlike amphiphilic molecules that contain exclusively aromatic building-blocks and no flexible alkyl chains have been synthesized and their mesomorphic properties investigated. These novel compounds bear diol head groups of different size (2,3-dihydroxypropyloxy or 5,6-dihydroxy-3-oxahexyloxy groups) at one end of a biphenyl unit, various aromatic segments (banzyloxy, 4-, 3-, or 2-methylbenzyloxy, phenoxy groups) at the other, and additional methyl substituents in different positions. They were synthesized by using Suzuki cross-coupling reactions as the key steps. Their thermotropic mesomorphism was investigated by means of polarized light optical microscopy, differential scanning calorimetry, and, for enantiotropic phases, by X-ray scattering. The liquid crystallinity of this class of compounds is influenced by protic solvents, such as water and glycerol. Dependent on the temperature and the solvent content, different S-A phases were found. Several mesophases resulting from the frustration of these layer structures (e.g., different columnar phases, optical isotropic mesophases, and nematic phases) were also present. The smectic phases have different degrees of intercalation (S-Ad, S-A2) The columnar phases are supposed to be ribbon structures that result from the collapse of the smectic layers. They occur in some pure compounds or they are induced upon the addition of protic solvents. The particular phase sequences of the different compounds depend mainly on the position of the methyl substituents at the biphenyl cores and are largely determined by the degree of intercalation of the aromatic cores.