ethyl 6-(chloromethyl)-2-methoxybenzoate | 81625-30-1

• 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: ethyl 6-(chloromethyl)-2-methoxybenzoate
• 英文别名: Ethyl 2-(chloromethyl)-6-methoxybenzoate
• CAS: 81625-30-1
• 化学式: C₁₁H₁₃ClO₃
• 分子量: 228.675
• InChiKey: WINFWQFOUOHWFG-UHFFFAOYSA-N

物化性质

• 沸点：
  105-112 °C(Press: 0.55 Torr)
• 密度：
  1.169±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 6-(chloromethyl)-2-methoxybenzoate 在 sodium hydroxide 、 sodium amalgam 、 lithium diisopropyl amide 作用下， 以 水 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 生成 2-Methoxy-6-<(Z)-10-pentadecenyl>benzoic acid
  参考文献：
  名称：

  Prostaglandin Synthetase Inhibitors from the African Medicinal PlantOzoroa mucronata

  摘要：

  从O. mucronata中分离出了两种前列腺素合酶抑制剂——酚酸。通过光谱法确定了这些抑制剂的结构。报道了通过定向金属化合成这两种物质的高效方法。

  DOI：

  10.1246/cl.1987.1101
• 作为产物：
  描述：

  N,N-dimethyl-2-(ethoxycarbonyl)-3-methoxybenzylamine 在 氯甲酸乙酯 作用下， 以 氯仿 为溶剂， 反应 0.25h， 以94%的产率得到ethyl 6-(chloromethyl)-2-methoxybenzoate
  参考文献：
  名称：

  Synthesis of 1,2,3,4-tetrahydroisoquinolines

  摘要：

  DOI：

  10.1021/jo00134a025

文献信息

• Syntheses of anacardic acids and ginkgoic acid
  作者：Yoshiro Yamagiwa、Kinji Ohashi、Yoshitaka Sakamota、Shinji Hirakawa、Tadao Kamikawa、Isao Kubo

  DOI：10.1016/s0040-4020(01)81629-x

  日期：——

  Syntheses of two anacardic acids [6-pentadecyl- and 6-(10-pentadecenyl) salicylic acid], inhibitors of prostaglandin synthetase and of the growth of certain insects, and ginkgoic acid via directive metallation is reported.

  据报导，合成了两种漆树酸[6-十五烷基和6-（10-十五碳烯基）水杨酸]，前列腺素合成酶的抑制剂和某些昆虫的生长，以及通过定向金属化作用生成的银杏酸。
• Synthetic studies of thiazoline and thiazolidine-containing natural products — 1. Phosphorus pentachloride-mediated thiazoline construction reaction
  作者：Akira Ino、Akira Murabayashi

  DOI：10.1016/s0040-4020(99)00582-7

  日期：1999.8

  Phosphorus pentachloride effectively mediates the cyclization of N-acylcysteamine derivatives giving rise to thiazoline rings. Using this method, sterically hindered thiazoline analogs could be constructed and thus segment A (the left half) of micacocidin, a unique antimycoplasma antibiotic, was synthesized efficiently.

  五氯化磷可有效​​介导N-酰基半胱胺衍生物的环化反应，产生噻唑啉环。使用这种方法，可以构建空间受阻的噻唑啉类似物，从而有效合成了micacocidin的A段（左半部分），一种独特的抗支原体抗生素。
• Discovery, Total Synthesis, and SAR of Anaenamides A and B: Anticancer Cyanobacterial Depsipeptides with a Chlorinated Pharmacophore
  作者：David A. Brumley、Sarath P. Gunasekera、Qi-Yin Chen、Valerie J. Paul、Hendrik Luesch

  DOI：10.1021/acs.orglett.0c01281

  日期：2020.6.5

  New modified depsipeptides and geometric isomers, termed anaenamides A (1a) and B (1b), along with the presumptive biosynthetic intermediate, anaenoic acid (2), were discovered from a marine cyanobacterium from Guam. Structures were confirmed by total synthesis. The alkylsalicylic acid fragment and the C-terminal α-chlorinated α,β-unsaturated ester are novelties in cyanobacterial natural products.

  从关岛的海洋蓝细菌中发现了新的修饰的十肽和几何异构体，称为酰胺A（1a）和B（1b），以及假定的生物合成中间体花生酸（2）。通过全合成确认结构。在蓝藻天然产物中，烷基水杨酸片段和C端α-氯代α，β-不饱和酯是新颖的。癌细胞活力分析表明，C末端单元起药效基团作用，双键几何结构影响细胞毒性。
• Combined coinage metal catalysis in natural product synthesis: total synthesis of (+)-varitriol and seven analogs
  作者：Tao Sun、Carl Deutsch、Norbert Krause

  DOI：10.1039/c2ob25069a

  日期：——

  A modular total synthesis of the natural product (+)-varitriol (1) and seven analogs was achieved by using combined coinage metal catalysis. Starting from enynol 13, reagent-controlled introduction of stereogenic centers and efficient center-to-axis-to-center chirality transfer via α-hydroxyallene 5 afforded (+)-varitriol with 6.4% yield over 10 steps.

  天然产物的模块化全合成 （+）-曲三醇（1）和七个类似物是通过组合造币金属催化制备的。从enynol开始13，试剂控制的引入手性中心，高效的经由中心到轴到中心的手性转移α-hydroxyallene 5，得到（+）-曲三醇 10步产率为6.4％。
• Anacardic acid derivatives as inhibitors of glyceraldehyde-3-phosphate dehydrogenase from Trypanosoma cruzi
  作者：Junia M. Pereira、Richele P. Severino、Paulo C. Vieira、João B. Fernandes、M. Fátima G.F. da Silva、Aderson Zottis、Adriano D. Andricopulo、Glaucius Oliva、Arlene G. Corrêa

  DOI：10.1016/j.bmc.2008.08.057

  日期：2008.10

  Chagas' disease, a parasitic infection caused by the flagellate protozoan Trypanosoma cruzi, is a major public health problem affecting millions of individuals in Latin America. On the basis of the essential role in the life cycle of T. cruzi, the glycolytic enzyme glyceraldehyde-3-phosphate dehydrogenase (GAPDH) has been considered an attractive target for the development of novel antitrypanosomatid agents. In the present work, we describe the inhibitory effects of a small library of natural and synthetic anacardic acid derivatives against the target enzyme. The most potent inhibitors, 6-n-pentadecyl-(1) and 6-n-dodecylsalicilic acids (10e), have IC50 values of 28 and 55 mu M, respectively. The inhibition was not reversed or prevented by the addition of Triton X-100, indicating that aggregate-based inhibition did not occur. In addition, detailed mechanistic characterization of the effects of these compounds on the T. cruzi GAPDH-catalyzed reaction showed clear noncompetitive inhibition with respect to both substrate and cofactor. (C) 2008 Elsevier Ltd. All rights reserved.