2-(4-丙基-苯氧基)-丙酸 | 25141-02-0

• 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: 2-(4-丙基-苯氧基)-丙酸
• 英文名称: 2-(4-propyl-phenoxy)-propionic acid
• 英文别名: 2-(4-Propylphenoxy)propanoic acid
• CAS: 25141-02-0
• 化学式: C₁₂H₁₆O₃
• mdl: MFCD09718009
• 分子量: 208.257
• InChiKey: BCGAQLXZWYPDCJ-UHFFFAOYSA-N

物化性质

• 沸点：
  330.8±17.0 °C(Predicted)
• 密度：
  1.091±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.416
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2918990090

反应信息

• 作为反应物：
  描述：

  2-(4-丙基-苯氧基)-丙酸 、 正丁醇 在 磷脂酶B disodium hydrogenphosphate 作用下， 以 异丙醚 为溶剂， 反应 22.0h， 生成 butyl (2R)-2-(4-propylphenoxy)propanoate
  参考文献：
  名称：

  Lyophilization of Lipase Together with Ionic Compounds Generates Highly Enantioselective and Solvent-sensitive Lipase in Organic Solvents

  摘要：

  从含有离子化合物（如磷酸氢二钠）的水相酶溶液中冻干的脂肪酶在有机溶剂中的酯化反应的对映选择性得到了显著提高，与不含离子化合物的脂肪酶相比。带有离子化合物涂层的脂肪酶的对映选择性对溶剂的变化相当敏感。

  DOI：

  10.1246/cl.2005.110
• 作为产物：
  描述：

  4-丙基苯酚 、 2-溴丙酸乙酯 生成 2-(4-丙基-苯氧基)-丙酸
  参考文献：
  名称：

  GB916242

  摘要：

  公开号：

文献信息

• Effects of Chiral Additives on Enantioselectivity for Lipase-Catalyzed Esterifications in an Organic Solvent. A Remarkable Enhancement of Its Enantioselectivity Due to Cooperative Effects of Two Kinds of Additives
  作者：Shin-ichi Ueji、Hideyuki Sakamoto、Keiichi Watanabe、Takashi Okamoto、Shuichi Mori

  DOI：10.1246/bcsj.75.2239

  日期：2002.10

  The enantioselectivity for the lipase-catalyzed esterifications in an organic solvent was found to be enhanced by addition of (+)- or (−)-camphor as a chiral additive. A more remarkable enhancement of its enantioselectivity was brought about by the cooperative effects of two kinds of additives: (−)-camphor and water.

  在有机溶剂中加入(+)-或(-)-樟脑作为手性添加剂，可提高脂肪酶催化酯化反应的对映选择性。(-)-樟脑和水这两种添加剂的协同作用更显著地提高了其对映体选择性。
• PROTEASOME CHYMOTRYPSIN-LIKE INHIBITION USING PI-1833 ANALOGS
  申请人：H. Lee Moffitt Cancer Center and Research Institute, Inc

  公开号：US20140073650A1

  公开（公告）日：2014-03-13

  Focused library synthesis and medicinal chemistry on an oxadiazole-isopropylamide core proteasome inhibitor provided the lead compound that strongly inhibits CT-L activity. Structure activity relationship studies indicate the amide moiety and two phenyl rings are sensitive toward synthetic modifications. Only para-substitution in the A-ring was important to maintain potent CT-L inhibitory activity. Hydrophobic residues in the A-ring's para-position and meta-pyridyl group at the B-ring significantly improved inhibition. The meta-pyridyl moiety improved cell permeability. The length of the aliphatic chain at the para position of the A-ring is critical with propyl yielding the most potent inhibitor, whereas shorter (i.e. ethyl, methyl or hydrogen) or longer (i.e. butyl, propyl and hexyl) chains demonstrating progressively less potency. Introduction of a stereogenic center next to the ether moiety (i.e. substitution of one of the hydrogens by methyl) demonstrated chiral discrimination in proteasome CT-L activity inhibition (the S-enantiomer was 35-40 fold more potent than the R-enantiomer).

  聚焦于氧代二唑-异丙酰胺核心蛋白酶体抑制剂的合成和药物化学，提供了一种强烈抑制CT-L活性的先导化合物。结构活性关系研究表明，酰胺基团和两个苯环对合成修饰非常敏感。只有在A环上的对位取代对维持强效的CT-L抑制活性至关重要。A环对位的疏水基团和B环的间吡啶基团显著提高了抑制作用。间吡啶基团提高了细胞渗透性。A环对位的脂肪链长度是关键，丙基产生了最有效的抑制剂，而较短（即乙基，甲基或氢）或较长（即丁基，异丙基和己基）的链逐渐表现出较少的效力。在醚基团旁引入一个立体异构中心（即将一个氢原子取代为甲基）表明在蛋白酶体CT-L活性抑制中具有手性歧视（S-对映体比R-对映体更有效，效力提高了35-40倍）。
• Proteasome chymotrypsin-like inhibition using PI-1833 analogs
  申请人：H. Lee Moffitt Cancer Center and Research Institute, Inc.

  公开号：US10662180B2

  公开（公告）日：2020-05-26

  Focused library synthesis and medicinal chemistry on an oxadiazole-isopropylamide core proteasome inhibitor provided the lead compound that strongly inhibits CT-L activity. Structure activity relationship studies indicate the amide moiety and two phenyl rings are sensitive toward synthetic modifications. Only para-substitution in the A-ring was important to maintain potent CT-L inhibitory activity. Hydrophobic residues in the A-ring's para-position and meta-pyridyl group at the B-ring significantly improved inhibition. The meta-pyridyl moiety improved cell permeability. The length of the aliphatic chain at the para position of the A-ring is critical with propyl yielding the most potent inhibitor, whereas shorter (i.e. ethyl, methyl or hydrogen) or longer (i.e. butyl, propyl and hexyl) chains demonstrating progressively less potency. Introduction of a stereogenic center next to the ether moiety (i.e. substitution of one of the hydrogens by methyl) demonstrated chiral discrimination in proteasome CT-L activity inhibition (the S-enantiomer was 35-40 fold more potent than the R-enantiomer).

  通过对一种噁二唑-异丙基酰胺核心蛋白酶体抑制剂进行重点文库合成和药物化学研究，获得了能强烈抑制 CT-L 活性的先导化合物。结构活性关系研究表明，酰胺分子和两个苯基环对合成修饰很敏感。只有 A 环中的对位取代对保持 CT-L 的强效抑制活性非常重要。A 环的对位疏水残基和 B 环的元吡啶基能显著改善抑制作用。偏吡啶基提高了细胞渗透性。A 环对位脂肪族链的长度至关重要，丙基产生的抑制作用最强，而较短的链（即乙基、甲基或氢基）或较长的链（即丁基、丙基和己基）的抑制作用则逐渐减弱。在醚分子旁边引入一个立体中心（即用甲基取代其中一个氢）可在蛋白酶体 CT-L 活性抑制方面显示出手性差异（S-对映体的效力比 R-对映体高 35-40 倍）。
• Ueji, Shin-ichi; Nishimura, Miyuki; Kudo, Risa, Chemistry Letters, 2001, # 9, p. 912 - 913
  作者：Ueji, Shin-ichi、Nishimura, Miyuki、Kudo, Risa、Matsumi, Rina、Watanabe, Keiichi、Ebara, Yasuhito

  DOI：——

  日期：——
• HETEROCYCLIC CETP INHIBITORS
  申请人：Bristol-Myers Squibb Company

  公开号：EP1951690B1

  公开（公告）日：2012-03-28