2-(2-butoxy-2-oxoethyl)benzoic acid | 1034706-10-9

• 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: 2-(2-butoxy-2-oxoethyl)benzoic acid
• CAS: 1034706-10-9
• 化学式: C₁₃H₁₆O₄
• 分子量: 236.268
• InChiKey: YGVVGHZQWQQTED-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.27
• 重原子数：
  17.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  63.6
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-(2-butoxy-2-oxoethyl)benzoic acid 在 五氯化磷 作用下， 以 苯 为溶剂， 反应 16.0h， 以75%的产率得到3-butoxy-4-chloroisocoumarin
  参考文献：
  名称：

  Isocoumarin-based inhibitors of pancreatic cholesterol esterase

  摘要：

  Pancreatic cholesterol esterase (CEase), which is secreted from the exocrine pancreas, is a serine hydrolase that aids in the bile salt-dependent hydrolysis of dietary cholesteryl esters and contributes to the hydrolysis of triglycerides and phospholipids. Additional roles for CEase in intestinal micelle formation and in transport of free cholesterol to the enterocyte have been suggested. There also are studies that point to a pathological role(s) for CEase in the circulation where CEase accumulates in atherosclerotic lesions and triggers proliferation of smooth muscle cells. Thus, there is interest in CEase as a potential drug target. 4-Chloro-3-alkoxyisocoumarins are a class of haloenol lactones that inhibit serine hydrolases and serine proteases and have the potential to be suicide inhibitors. In the present study, we have developed 3-alkoxychloroisocoumarins that are potent inhibitors of CEase. These inhibitors were designed to have a saturated cycloalkane ring incorporated into a 3-alkoxy substituent. The size of the ring as well as the length of the tether holding the ring was found to be important contributors to binding to CEase. 4-Chloro-3-(4-cyclohexylbutoxy) isocoumarin and 4-chloro-3-(3-cyclopentylpropoxy) isocoumarin were demonstrated to be potent reversible inhibitors of CEase, with dissociation constants of 11 nM and 19 nM, respectively. The kinetic results are consistent with predictions from molecular modeling. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.03.016
• 作为产物：
  描述：

  邻羧基苯乙酸 、 正丁醇 在 碘 、 三苯基膦 作用下， 以 乙腈 为溶剂， 反应 0.75h， 以94%的产率得到2-(2-butoxy-2-oxoethyl)benzoic acid
  参考文献：
  名称：

  微波辅助的高度实用的羧酸的化学选择性酯化和酰胺化†

  摘要：

  酯和酰胺官能团无处不在，使它们的偶联反应成为最受欢迎的有机转化之一。在此，我们已经描述了酯和酰胺的有效微波辅助合成。可溶性三苯基膦与分子碘结合，可得到所需的产物，而无需碱/催化剂。另外，为所述转化引入了固相合成路线，其与溶液相路线相比具有更多的优点，例如低湿度敏感性，易于处理，通过简单过滤分离产物和可重复使用性。简而言之，我们的方法本质上是简单，温和，绿色和高度化学选择性的。

  DOI：

  10.1039/c6ra22558f

文献信息

• Highly Chemoselective Esterification Reactions and Boc/THP/TBDMS Discriminating Deprotections under Samarium(III) Catalysis
  作者：Pushparathinam Gopinath、Surapaneni Nilaya、Kannoth Manheri Muraleedharan

  DOI：10.1021/ol200247c

  日期：2011.4.15

  The usefulness of SmCl(3) as an excellent catalyst for chemoselective esterifications and selective removal of acid sensitive protecting groups such as Boc, THP, and TBDMS in the presence of one another is demonstrated through suitable examples.
• 4-Chloroisocoumarins as Chlamydial Protease Inhibitors and Anti-Chlamydial Agents
  作者：Matthew J. A. Phillips、Wilhelmina M. Huston、Andrew M. McDonagh、Tristan Rawling

  DOI：10.3390/molecules29071519

  日期：——

  4-Chloroisocoumarin compounds have broad inhibitory properties against serine proteases. Here, we show that selected 3-alkoxy-4-chloroisocoumarins preferentially inhibit the activity of the conserved serine protease High-temperature requirement A of Chlamydia trachomatis. The synthesis of a new series of isocoumarin-based scaffolds has been developed, and their anti-chlamydial properties were investigated. The structure of the alkoxy substituent was found to influence the potency of the compounds against High-temperature requirement A, and modifications to the C-7 position of the 3-alkoxy-4-chloroisocoumarin structure attenuate anti-chlamydial properties.