(2-ethoxycarbonyl-3-methoxybenzyl)triphenylphosphonium chloride | 110202-78-3

• 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-ethoxycarbonyl-3-methoxybenzyl)triphenylphosphonium chloride
• 英文别名: 2-ethoxycarbonyl-3-methoxybenzyltriphenylphosphonium chloride；(2-Ethoxycarbonyl-3-methoxyphenyl)methyl-triphenylphosphanium;chloride
• CAS: 110202-78-3
• 化学式: C₂₉H₂₈O₃P*Cl
• 分子量: 490.966
• InChiKey: WHGYKYPAKBMXTJ-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  2.37
• 重原子数：
  34
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2-ethoxycarbonyl-3-methoxybenzyl)triphenylphosphonium chloride 在 platinum on activated charcoal 氢气 、 三溴化硼 、 lithium hexamethyldisilazane 作用下， 以 水 、 二甲基亚砜 为溶剂， 生成 氢化白果酸
  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：

  ethyl 6-(chloromethyl)-2-methoxybenzoate 、 三苯基膦 生成 (2-ethoxycarbonyl-3-methoxybenzyl)triphenylphosphonium chloride
  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

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。
• Total synthesis of the antimycoplasma antibiotic micacocidin
  作者：Akira Ino、Yasushi Hasegawa、Akira Murabayashi

  DOI：10.1016/s0040-4039(98)00518-8

  日期：1998.5

  A total synthesis of the antimycoplasma antibiotic micacocidin (1) is described. Construction of sterically hindered thiazoline 12 was achieved by a phosphorus pentachloride-mediated cyclization reaction of S-protected aryloylcysteine 11, and compound 1 with desired chirality at C-10 was favorably obtained from diastereomeric mixture 30 through formation of the Zn complex 31. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Prostaglandin Synthetase Inhibitors from the African Medicinal Plant<i>Ozoroa mucronata</i>
  作者：Isao Kubo、Mujo Kim、Keizo Naya、Sakae Komatsu、Yoshiro Yamagiwa、Kinji Ohashi、Yoshitaka Sakamoto、Shinji Hirakawa、Tadao Kamikawa

  DOI：10.1246/cl.1987.1101

  日期：1987.6.5

  Two prostaglandin synthetase inhibitory anacardic acids were isolated from O. mucronata. The structures of these inhibitors were established by spectroscopic means. Efficient syntheses of these two via directive metallation were reported.

  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。
• 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.