3-(2-amino-4-benzyloxyphenyl)acrylic acid methyl ester | 183007-34-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 3-(2-amino-4-benzyloxyphenyl)acrylic acid methyl ester
• 英文别名: Methyl 3-(2-amino-4-phenylmethoxyphenyl)prop-2-enoate
• CAS: 183007-34-3
• 化学式: C₁₇H₁₇NO₃
• 分子量: 283.327
• InChiKey: IXOFAOAATDHJNV-UHFFFAOYSA-N

物化性质

• 沸点：
  478.4±40.0 °C(Predicted)
• 密度：
  1.193±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  61.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(2-amino-4-benzyloxyphenyl)acrylic acid methyl ester 在 吡啶 、 偶氮二异丁腈 、 三光气 、 三正丁基氢锡 、 三乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 7.0h， 生成 (6-benzyloxy-1H-indol-3-yl)acetic acid methyl ester
  参考文献：
  名称：

  Design and synthesis of alkoxyindolyl-3-acetic acid analogs as peroxisome proliferator-activated receptor-γ/δ agonists

  摘要：

  A series of carbazole or phenoxazine containing alkoxyindole-3-acetic acid analogs were prepared as PPAR gamma/delta agonists and their transactivation activities for PPAR receptor subtypes (alpha, gamma and delta) were investigated. Structure-activity relationship studies disclosed the effect of the lipophilic tail, attaching position of the alkoxy group and N-benzyl substitution at indole. Compound 1b was the most potent for PPARd and 3b for PPAR gamma. Molecular modeling suggested two different binding modes of our alkoxyindole-3-acetic acid analogs providing the insight into their PPAR activity. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.11.033
• 作为产物：
  描述：

  4-碘-3-硝基苯酚 在 palladium diacetate 、 potassium carbonate 、 溶剂黄146 、 三乙胺 、 三对苯甲基膦 、 锌 作用下， 以 丙酮 、 乙腈 为溶剂， 反应 1.5h， 生成 3-(2-amino-4-benzyloxyphenyl)acrylic acid methyl ester
  参考文献：
  名称：

  Design and synthesis of alkoxyindolyl-3-acetic acid analogs as peroxisome proliferator-activated receptor-γ/δ agonists

  摘要：

  A series of carbazole or phenoxazine containing alkoxyindole-3-acetic acid analogs were prepared as PPAR gamma/delta agonists and their transactivation activities for PPAR receptor subtypes (alpha, gamma and delta) were investigated. Structure-activity relationship studies disclosed the effect of the lipophilic tail, attaching position of the alkoxy group and N-benzyl substitution at indole. Compound 1b was the most potent for PPARd and 3b for PPAR gamma. Molecular modeling suggested two different binding modes of our alkoxyindole-3-acetic acid analogs providing the insight into their PPAR activity. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.11.033