methyl 2-[(3S)-6-[(1R)-1-[3-[2,6-dimethyl-4-(3-methylsulfonylpropoxy)phenyl]phenyl]-2-hydroxyethoxy]-5-iodo-2,3-dihydro-1-benzofuran-3-yl]acetate | 1432045-88-9

• 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: methyl 2-[(3S)-6-[(1R)-1-[3-[2,6-dimethyl-4-(3-methylsulfonylpropoxy)phenyl]phenyl]-2-hydroxyethoxy]-5-iodo-2,3-dihydro-1-benzofuran-3-yl]acetate
• CAS: 1432045-88-9
• 化学式: C₃₁H₃₅IO₈S
• 分子量: 694.585
• InChiKey: COMOPRXNCXYFMH-BTYSJIOQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  41
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  117
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl 2-[(3S)-6-[(1R)-1-[3-[2,6-dimethyl-4-(3-methylsulfonylpropoxy)phenyl]phenyl]-2-hydroxyethoxy]-5-iodo-2,3-dihydro-1-benzofuran-3-yl]acetate 在 1,1'-[(1S)-(1,1'-binaphthalene)-2,2'-diyl]bis[1,1-di-tert-butyl-phosphine] 、 palladium diacetate 、 caesium carbonate 作用下， 以 甲苯 为溶剂， 反应 12.0h， 以46%的产率得到methyl 2-[(3R,8S)-3-[3-[2,6-dimethyl-4-(3-methylsulfonylpropoxy)phenyl]phenyl]-2,3,7,8-tetrahydrofuro[2,3-g][1,4]benzodioxin-8-yl]acetate
  参考文献：
  名称：

  Discovery of novel orally bioavailable GPR40 agonists

  摘要：

  The GPR40 (FFA1) has emerged as an attractive target for a novel insulin secretagogue with glucose dependency. A series of novel orally bioavailable GPR40 agonists was discovered. SAR study and structural optimization led to identification of compounds 28a and 30a as potent GPR40 agonists with superior physiochemical properties and robust in vivo efficacy in rhesus monkeys. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.03.060
• 作为产物：
  描述：

  2,6-dimethyl-4-(3-(methylsulfonyl)propoxy)-3'-vinylbiphenyl 在 咪唑 、 4-二甲氨基吡啶 、 三丁基膦 、 AD-mix-α 、 四丁基氟化铵 、 1,1'-azodicarbonyl-dipiperidine 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 、 甲苯 、 叔丁醇 为溶剂， 反应 7.0h， 生成 methyl 2-[(3S)-6-[(1R)-1-[3-[2,6-dimethyl-4-(3-methylsulfonylpropoxy)phenyl]phenyl]-2-hydroxyethoxy]-5-iodo-2,3-dihydro-1-benzofuran-3-yl]acetate
  参考文献：
  名称：

  Discovery of novel orally bioavailable GPR40 agonists

  摘要：

  The GPR40 (FFA1) has emerged as an attractive target for a novel insulin secretagogue with glucose dependency. A series of novel orally bioavailable GPR40 agonists was discovered. SAR study and structural optimization led to identification of compounds 28a and 30a as potent GPR40 agonists with superior physiochemical properties and robust in vivo efficacy in rhesus monkeys. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.03.060