4-((4-bromo-3-methylphenoxy)methyl)-2,2-dimethyl-1,3-dioxolane | 309947-16-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-((4-bromo-3-methylphenoxy)methyl)-2,2-dimethyl-1,3-dioxolane
• 英文别名: 4-[(4-bromo-3-methylphenoxy)methyl]-2,2-dimethyl-1,3-dioxolane
• CAS: 309947-16-8
• 化学式: C₁₃H₁₇BrO₃
• 分子量: 301.18
• InChiKey: XMWPGTQMQAUDGD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-((4-bromo-3-methylphenoxy)methyl)-2,2-dimethyl-1,3-dioxolane 在 palladium on activated charcoal 、 四(三苯基膦)钯 水 、 氢气 、 4-甲基苯磺酸吡啶 、 碳酸氢钠 、 potassium carbonate 作用下， 以 甲醇 、 乙二醇二甲醚 、 乙酸乙酯 、 丙酮 为溶剂， 反应 14.0h， 生成 3-[2-Methyl-4'-(3-methylbenzyloxy)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：

  1-Allyloxy-4-bromo-3-methylbenzene 在 四氧化锇 、 N-甲基吲哚酮 、 水 、 4-甲基苯磺酸吡啶 作用下， 以 丙酮 、 叔丁醇 为溶剂， 生成 4-((4-bromo-3-methylphenoxy)methyl)-2,2-dimethyl-1,3-dioxolane
  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

• GPR40 AGONISTS IN ANTI-DIABETIC DRUG COMBINATIONS
  申请人：Janssen Pharmaceutica NV

  公开号：US20170290800A1

  公开（公告）日：2017-10-12

  Disclosed are compositions comprising (a) a GPR40 agonist and (b) an SGLT2 inhibitor, and methods for treating of disorders that are affected by the modulation of the GPR40 receptor and SGLT2 transporter. Such GPR40 compounds are represented by Formula (I) as follows: wherein ring W, R 1 , R 2 , R 3 , R 5 , R 6 , A, and Z, are defined herein.

  本文披露了包含（a）GPR40激动剂和（b）SGLT2抑制剂的组合物，以及治疗受GPR40受体和SGLT2转运蛋白调节影响的疾病的方法。这些GPR40化合物由以下式（I）表示： 其中环W，R1，R2，R3，R5，R6，A和Z在此处被定义。
• SUBSTITUTED BENZOTHIOPHENYL DERIVATIVES AS GPR40 AGONISTS FOR THE TREATMENT OF TYPE II DIABETES
  申请人：Janssen Pharmaceutica NV

  公开号：US20170291908A1

  公开（公告）日：2017-10-12

  Disclosed are compounds, compositions and methods for treating of disorders that are affected by the modulation of the GPR40 receptor. Such compounds are represented by Formula (I) as follows: wherein U 1 , U 2 , U 3 , R 1 , R 2 , Z, and W are defined herein.

  揭示了一种通过调节GPR40受体来治疗受影响疾病的化合物、组合物和方法。这些化合物由以下式（I）表示： 其中U1、U2、U3、R1、R2、Z和W在此处定义。
• [EN] SUBSTITUTED BENZOTHIOPHENYL DERIVATIVES AS GPR40 AGONISTS FOR THE TREATMENT OF TYPE II DIABETES<br/>[FR] DÉRIVÉS DE BENZOTHIAZOLE SUBSTITUÉS UTILISÉS EN TANT QU'AGONISTES DE GPR40 POUR LE TRAITEMENT DU DIABÈTE DE TYPE II
  申请人：JANSSEN PHARMACEUTICA NV

  公开号：WO2016057731A1

  公开（公告）日：2016-04-14

  Disclosed are compounds, compositions and methods for treating of disorders that are affected by the modulation of the GPR40 receptor. Such compounds are represented by Formula (I) wherein R1, R2, R3, R5, R6, W, and A are defined herein.

  揭示了一种通过调节GPR40受体来治疗受影响疾病的化合物、组合物和方法。这些化合物由式（I）所代表，其中R1、R2、R3、R5、R6、W和A在此处被定义。
• Substituted benzothiophenyl derivatives as GPR40 agonists for the treatment of type II diabetes
  申请人：Janssen Pharmaceutica NV

  公开号：US10106553B2

  公开（公告）日：2018-10-23

  Disclosed are compounds, compositions and methods for treating of disorders that are affected by the modulation of the GPR40 receptor. Such compounds are represented by Formula (I) as follows: wherein U1, U2, U3, R1, R2, Z, and W are defined herein.

  公开了用于治疗受 GPR40 受体调节影响的疾病的化合物、组合物和方法。此类化合物由如下式（I）表示： 其中 U1、U2、U3、R1、R2、Z 和 W 在此定义。
• GPR40 agonists in anti-diabetic drug combinations
  申请人：Janssen Pharmaceutica NV

  公开号：US10195178B2

  公开（公告）日：2019-02-05

  Disclosed are compositions comprising (a) a GPR40 agonist and (b) an SGLT2 inhibitor, and methods for treating of disorders that are affected by the modulation of the GPR40 receptor and SGLT2 transporter. Such GPR40 compounds are represented by Formula (I) as follows: wherein ring W, R1, R2, R3, R5, R6, A, and Z, are defined herein.

  公开了包含(a)GPR40激动剂和(b)SGLT2抑制剂的组合物，以及治疗受GPR40受体和SGLT2转运体调节影响的疾病的方法。此类 GPR40 化合物由如下式 (I) 表示： 其中环 W、R1、R2、R3、R5、R6、A 和 Z 在此定义。