1-溴-3-[(4-乙基苯基)甲基]苯 | 333360-86-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-溴-3-[(4-乙基苯基)甲基]苯
• 英文名称: 3-bromo-(4'-ethyl)-diphenylmethane
• 英文别名: 1-bromo-3-(4-ethylbenzyl)benzene；1-bromo-3-[(4-ethylphenyl)methyl]benzene
• CAS: 333360-86-4
• 化学式: C₁₅H₁₅Br
• 分子量: 275.188
• InChiKey: VWTRBKRCEWHYMC-UHFFFAOYSA-N

物化性质

• 沸点：
  346.2±11.0 °C(Predicted)
• 密度：
  1.263±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1-溴-3-[(4-乙基苯基)甲基]苯 在 四(三苯基膦)钯 potassium phosphate 、 正丁基锂 、 五甲基苯 、 硫酸 、 水 、 三氯化硼 、 potassium bromide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 正己烷 、 二氯甲烷 、 水 为溶剂， 反应 41.5h， 生成 (1R,2S,3S,6R)-4-[3-(4-ethylbenzyl)phenyl]-6-(hydroxymethyl)cyclohex-4-ene-1,2,3-triol
  参考文献：
  名称：

  EP1783110

  摘要：

  公开号：
• 作为产物：
  描述：

  间溴苯甲醛 在 三乙基硅烷 、 三氟化硼乙醚 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.17h， 生成 1-溴-3-[(4-乙基苯基)甲基]苯
  参考文献：
  名称：

  C-Aryl 5a-carba-β-d-glucopyranosides as novel sodium glucose cotransporter 2 (SGLT2) inhibitors for the treatment of type 2 diabetes

  摘要：

  C-Aryl 5a-carba-beta-D-glucopyranose derivatives were synthesized and evaluated for inhibition activity against hSGLT1 and hSGLT2. Modifications to the substituents on the two benzene rings resulted in enhanced hSGLT2 inhibition activity and extremely high hSGLT2 selectivity versus SGLT1. Using the created superimposed model, the reason for the high hSGLT2 selectivity was speculated to be that additional substituents occupied a new space, in a different way than known inhibitors. Among the tested compounds, the ethoxy compound 5h with high hSGLT2 selectivity exhibited more potent and longer hypoglycemic action in db/db mice than our O-carbasugar compound (1) and sergliflozin (2), which could be explained by its improved PK profiles relative to those of the two compounds. These results indicated that 5h might be a promising drug candidate for the treatment of type 2 diabetes. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.04.053

文献信息

• Novel aromatic fluoroglycoside derivatives, pharmaceuticals comprising said compounds and the use thereof
  申请人：FRICK Wendelin

  公开号：US20110059910A1

  公开（公告）日：2011-03-10

  The invention relates to substituted aromatic fluoroglycoside derivatives, and to the physiologically compatible salts and physiologically functional derivatives thereof. The invention also relates to methods of lowering blood sugar and the treatment of type I and type II diabetes.

  这项发明涉及取代芳香族氟糖苷衍生物，以及其生理兼容盐和生理功能衍生物。该发明还涉及降低血糖和治疗I型和II型糖尿病的方法。
• C-aryl glucoside SGLT2 inhibitors and method
  申请人：——

  公开号：US20030114390A1

  公开（公告）日：2003-06-19

  A method is provided for treating diabetes and related diseases employing an SGLT2 inhibiting amount of a compound of the formula 1 alone or in combination with one or more other antidiabetic agent(s) or other therapeutic agent(s).

  提供了一种用于治疗糖尿病及相关疾病的方法，使用化合物formula1的SGLT2抑制剂量，可以单独使用，也可以与一个或多个其他抗糖尿病药物或其他治疗药物组合使用。
• A Practical Stereoselective Synthesis and Novel Cocrystallizations of an Amphiphatic SGLT-2 Inhibitor
  作者：Prashant P. Deshpande、Janak Singh、Annie Pullockaran、Thomas Kissick、Bruce A. Ellsworth、Jack Z. Gougoutas、John Dimarco、Michael Fakes、Mayra Reyes、Chiajen Lai、Hidegard Lobinger、Theo Denzel、Peter Ermann、Gerard Crispino、Michael Randazzo、Zenrong Gao、Renee Randazzo、Mark Lindrud、Victor Rosso、Frederic Buono、Wendel W. Doubleday、Simon Leung、Pricilla Richberg、David Hughes、William N. Washburn、Wei Meng、Kevin J. Volk、Richard H. Mueller

  DOI：10.1021/op200306q

  日期：2012.4.20

  stereoselective reduction of a methyl C-aryl peracetylated glycoside using a silyl hydride to set the stereochemistry of the crucial anomeric chiral center. Several novel cocrystalline complexes of 1 with l-phenylalanine and l-proline were discovered. Single-crystal structures of these complexes and several synthetic intermediates have been determined. The l-phenylalanine complex was developed and used to purify

  所述的一个实际的合成SGLT-2抑制剂β- ç -芳基- d葡糖苷（1）已被开发。路线采用2,3,4,6-四ö -trimethlysilyl- d -glucano -1,5-内酯作为关键手性砌块，从市售的廉价原料有效地制备，d -gluconolactone和三甲基氯硅烷。合成中的重要步骤是使用甲硅烷基氢化物设定关键的异头手性中心的立体化学，路易斯酸介导的甲基C-芳基过乙酰化的糖苷的立体选择性还原。的若干新颖共结晶态复合物1与升-苯丙氨酸和升脯氨酸被发现。这些配合物和几种合成中间体的单晶结构已经确定。该升苯丙氨酸复杂的开发和用于提纯和分离的API。所有步骤均以千克为单位实施。
• Methods of producing C-aryl glucoside SGLT2 inhibitors
  申请人：——

  公开号：US20040138439A1

  公开（公告）日：2004-07-15

  Method for the production of C-aryl glucoside SGLT2 inhibitors useful for the treatment of diabetes and related diseases. and intermediates thereof. The C-aryl glucosides may be complexed with amino acid complex forming reagents.

  用于生产治疗糖尿病和相关疾病的C-芳基葡萄糖苷SGLT2抑制剂的方法，以及其中间体。C-芳基葡萄糖苷可以与氨基酸复合物形成试剂形成复合物。
• Amino acid complexes of C-aryl glucosides for treatment of diabetes and method
  申请人：——

  公开号：US20030064935A1

  公开（公告）日：2003-04-03

  Crystalline complexes are obtained from a 1:1 or 2:1 mixtures of either the (D) or (L) enantiomer of natural amino acids and compounds of formula 1 wherein R 1 , R 2 and R 2a are independently hydrogen, OH, OR 5 , alkyl, —OCHF 2 , —OCF 3 , —SR 5a or halogen; R 3 and R 4 are independently hydrogen, OH, OR 5b , alkyl, cycloalkyl, CF 3 , —OCHF 2 , —OCF 3 , halogen, —CONR 6 R 6a , —CO 2 R 5c , —CO 2 H, —COR 6b , —CH(OH)R 6c , —CH(OR 5d )R 6d , —CN, —NHCOR 5e , —NHSO 2 R 5f , —NHSO 2 Aryl, —SR 5g , —SOR 5h , —SO 2 R 5i , or a five, six or seven membered heterocycle which may contain 1 to 4 heteroatoms in the ring which are N, O, S, SO, and/or SO 2 , or R 3 and R 4 together with the carbons to which they are attached form an annelated five, six or seven membered carbocycle or heterocycle which may contain 1 to 4 heteroatoms in the ring which are N, O, S, SO, and/or SO 2 ; R 5 , R 5a , R 5b , R 5c , R 5d , R 5e , R 5f , R 5g , R 5h and R 5i are independently alkyl; R 6 , R 6a , R 6b , R 6c and R 6d are independently hydrogen, alkyl, aryl, alkylaryl or cycloalkyl, or R 6 and R 6a together with the nitrogen to which they are attached form an annelated five, six or seven membered heterocycle which may contain 1 to 4 heteroatoms in the ring which are N, O, S, SO, and/or SO 2 . A method is also provided for treating diabetes and related diseases employing an SGLT2 inhibiting amount of the above complex alone or in combination with another antidiabetic agent or other therapeutic agent.

  从天然氨基酸的(D)或(L)对映体和具有公式1的化合物的1:1或2:1混合物中获得结晶配合物，其中R1、R2和R2a独立地为氢、OH、OR5、烷基、—OCHF2、—OCF3、—SR5a或卤素；R3和R4独立地为氢、OH、OR5b、烷基、环烷基、CF3、—OCHF2、—OCF3、卤素、—CONR6R6a、—CO2R5c、—CO2H、—COR6b、—CH(OH)R6c、—CH(OR5d)R6d、—CN、—NHCOR5e、—NHSO2R5f、—NHSO2芳基、—SR5g、—SOR5h、—SO2R5i，或者一个含有1至4个N、O、S、SO和/或SO2杂原子的五、六或七元杂环；R5、R5a、R5b、R5c、R5d、R5e、R5f、R5g、R5h和R5i独立地为烷基；R6、R6a、R6b、R6c和R6d独立地为氢、烷基、芳基、烷基芳基或环烷基，或者R6和R6a与它们连接的氮一起形成一个含有1至4个N、O、S、SO和/或SO2杂原子的五、六或七元杂环。还提供了一种用于治疗糖尿病和相关疾病的方法，该方法使用上述配合物的SGLT2抑制剂量单独或与另一种抗糖尿病药物或其他治疗药物联合使用。