2-hydroxyethyl 2-chlorobenzoate | 57027-67-5

• 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-hydroxyethyl 2-chlorobenzoate
• 英文别名: 2-chloro-benzoic acid-(2-hydroxy-ethyl ester)；Aethylenglykol-mono-(2-chlor-benzoat)；2-Chlor-benzoesaeure-(2-hydroxy-aethylester)；2-Chlor-benzoesaeure-(β-oxy-aethylester)
• CAS: 57027-67-5
• 化学式: C₉H₉ClO₃
• mdl: MFCD20257329
• 分子量: 200.622
• InChiKey: WYCXVGCNWREDFC-UHFFFAOYSA-N

物化性质

• 沸点：
  324.8±22.0 °C(Predicted)
• 密度：
  1.308±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-hydroxyethyl 2-chlorobenzoate 在 吡啶 、 palladium 10% on activated carbon 、 氢气 、 potassium carbonate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 20.0~80.0 ℃ 、1.0 MPa 条件下， 反应 25.0h， 生成
  参考文献：
  名称：

  三环萜类衍生物作为新型PTP1B抑制剂的设计和合成，具有改进的药理特性和体内抗高血糖功效。

  摘要：

  在各种基础和临床研究中，蛋白酪氨酸磷酸酶1B（PTP1B）的过表达诱导胰岛素抵抗。在我们以前的工作中，已经报道了具有PTP1B抑制活性的合成齐墩果酸（OA）衍生物C10a。但是，C10a具有一些药理缺陷和细胞毒性。在本文中，基于C10a的结构使用了基于结构的药物设计方法来完善较小的三环核心。合成了一系列三环衍生物，化合物15、28和34表现出最大的PTP1B酶促抑制能力。在具有胰岛素抵抗性的人肝癌HepG2细胞中，具有中等PTP1B抑制作用和较好药物特性的化合物25可以显着增加胰岛素刺激的葡萄糖摄取，并显示出改善胰岛素抵抗的作用。而且，图25显示了在烟酰胺-链脲佐菌素诱导的T2D中改善的体内抗高血糖潜能。我们的研究表明，这些具有改善的分子结构和抗高血糖活性的三环衍生物可用于治疗T2D。

  DOI：

  10.1080/14756366.2019.1690481
• 作为产物：
  描述：

  1,2-二氯乙烷 、 alkaline earth salt of/the/ methylsulfuric acid 在 水 作用下， 生成 2-hydroxyethyl 2-chlorobenzoate
  参考文献：
  名称：

  DE245532

  摘要：

  公开号：

文献信息

• Electrochemical esterification reaction of alkynes with diols <i>via</i> cleavage of carbon–carbon triple bonds without catalyst and oxidant
  作者：Pei-Long Wang、Hui-Zhi Shen、Hui-Hui Cheng、Hui Gao、Pin-Hua Li

  DOI：10.1039/d0gc02193h

  日期：——

  as it is catalyst-free, oxidant-free, and additive-free and shows atom-economy. This is the first example of an electrochemical reaction via cleavage of carbon–carbon triple bonds. Meanwhile, this is also the first example of a carbon–carbon triple bond cleavage reaction of alkynes with diols.

  开发了一种新型的炔烃电化学酯化反应，用于酯的合成，其中二醇及其衍生物用作伙伴。该方法是绿色的，因为它不含催化剂，不含氧化剂和添加剂，并且具有原子经济性。这是通过裂解碳-碳三键进行电化学反应的第一个例子。同时，这也是炔烃与二醇的碳-碳三键裂解反应的第一个例子。
• Novel Benzo-1,2,3-thiadiazole-7-carboxylate Derivatives As Plant Activators and the Development of Their Agricultural Applications
  作者：Qingshan Du、Weiping Zhu、Zhenjiang Zhao、Xuhong Qian、Yufang Xu

  DOI：10.1021/jf203974p

  日期：2012.1.11

  Plant activators are a novel kind of agrochemicals that could induce resistance in many plants against a broad spectrum of diseases. To date, only few plant activators have been commercialized. In order to develop novel plant activators, a series of benzo-1,2,3-thiadiazole-7-carboxylate derivatives were synthesized, and the structures were characterized by H-1 NMR, IR, elemental analyses, and HRMS or MS. Their potential systemic acquired resistance as plant activators was evaluated as well. Most of them showed good activity, especially, fluoro-containing compounds 3d and 3e, which displayed excellent SAR-inducing activity against cucumber Erysiphe cichoracearum and Colletotrichum lagenarium in assay screening. Field test results illustrated that compounds 3d and 3e were more potent than the commercial plant activator, S-methyl benzo[1,2,3]thiadiazole-7-carbothioate (BTH) toward these pathogens. Further, the preparation of compound 3d is more facile than BTH with lower cost, which will be helpful for further applications in agricultural plant protection.
• Novel, Unnatural Benzo-1,2,3-thiadiazole-7-carboxylate Elicitors of Taxoid Biosynthesis
  作者：Yufang Xu、Zhengjiang Zhao、Xuhong Qian、Zhigang Qian、Wenhong Tian、Jianjiang Zhong

  DOI：10.1021/jf0618574

  日期：2006.11.1

  In order to establish the chemical biological technology for production of valuable secondary metabolites, a novel family of unnatural elicitors derived from the plant activator benzo-1,2,3-thiadiazole-7-carboxylic acid were designed and synthesized. New synthetic elicitors that showed powerful eliciting activities upon taxoid biosynthesis by Taxus chinensis suspension cells were obtained. For example, benzo-1,2,3-thiadiazole-7-carboxylic acid 2-(2-hydroxybenzoxyl) ethyl ester was more effective and resulted in nearly 40% increase in taxuyunnanine C content and production in comparison with methyl jasmonate, which was previously reported as the most powerful chemical elicitor for taxoid biosynthesis. The novel class of elicitors was found to induce plant defense responses, including promotion of H2O2 levels originating from oxidative burst and activation of phenylalanine ammonia lyase. Interestingly the plant defense responses induced corresponded well to the superior stimulating activity in T. chinensis cell cultures. The work indicates that the newly synthesized benzothiadiazoles can act as a new family of elicitors for taxoid biosynthesis in plant cells.