3-(4-benzyloxy-2-isocyanophenyl)acrylic acid methyl ester | 183007-31-0

• 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-(4-benzyloxy-2-isocyanophenyl)acrylic acid methyl ester
• 英文别名: methyl 3-(2-isocyano-4-phenylmethoxyphenyl)prop-2-enoate
• CAS: 183007-31-0
• 化学式: C₁₈H₁₅NO₃
• 分子量: 293.322
• InChiKey: ZBCVIDBIPGDXSE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
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• 重原子数：
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• 可旋转键数：
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• 环数：
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• sp3杂化的碳原子比例：
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• 拓扑面积：
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• 氢给体数：
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• 氢受体数：
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反应信息

• 作为反应物：
  描述：

  3-(4-benzyloxy-2-isocyanophenyl)acrylic acid methyl ester 在 偶氮二异丁腈 、 三丁基膦 、 10 wt% Pd(OH)2 on carbon 、 水 、 氢气 、 三正丁基氢锡 、 sodium hydride 、 sodium hydroxide 、 1,1'-azodicarbonyl-dipiperidine 作用下， 以 四氢呋喃 、 甲醇 、 溶剂黄146 、 甲苯 、 mineral oil 为溶剂， 20.0~80.0 ℃ 、101.33 kPa 条件下， 反应 23.5h， 生成 2-[1-Benzyl-6-(3-carbazol-9-ylpropoxy)indol-3-yl]acetic acid
  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 吡啶 、 三光气 、 palladium diacetate 、 potassium carbonate 、 溶剂黄146 、 三乙胺 、 三对苯甲基膦 、 锌 作用下， 以 二氯甲烷 、 丙酮 、 乙腈 为溶剂， 反应 5.0h， 生成 3-(4-benzyloxy-2-isocyanophenyl)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