3-ethoxycarbonyloxybenzoic acid | 80172-02-7

• 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: 3-ethoxycarbonyloxybenzoic acid
• 英文别名: 3-ethoxycarbonyloxy-benzoic acid；3-Aethoxycarbonyloxy-benzoesaeure；3-(Carbaethoxy-oxy)-benzoesaeure
• CAS: 80172-02-7
• 化学式: C₁₀H₁₀O₅
• mdl: MFCD12068435
• 分子量: 210.186
• InChiKey: RACYQIFUABRHNE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-ethoxycarbonyloxybenzoic acid 在 草酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 3-ethoxycarbonyloxybenzoyl chloride
  参考文献：
  名称：

  Crystal Structure of the Homo sapiens Kynureninase-3-Hydroxyhippuric Acid Inhibitor Complex: Insights into the Molecular Basis Of Kynureninase Substrate Specificity

  摘要：

  Homo sapiens kynureninase is a pyridoxal-5'-phosphate dependent enzyme that catalyzes the hydrolytic cleavage of 3-hydroxykynurenine to yield 3-hydroxyanthranilate and L-alanine as part of the tryptophan catabolic pathway leading to the de novo biosynthesis of NAD(+). This pathway results in quinolinate, an excitotoxin that is an NMDA receptor agonist. High levels of quinolinate have been correlated with the etiology of neurodegenerative disorders such as AIDS-related dementia and Alzheimer's disease. We have synthesized a novel kynureninase inhibitor, 3-hydroxyhippurate, cocrystallized it with human kynureninase, and solved the atomic structure. On the basis of an analysis of the complex, we designed a series of His-102, Ser-332, and Asn-333 mutants. The H102W/N333T and H102W/S332G/N333T mutants showed complete reversal of substrate specificity between 3-hydroxykynurenine and L-kynurenine, thus defining the primary residues contributing to substrate specificity in kynureninases.

  DOI：

  10.1021/jm8010806
• 作为产物：
  描述：

  ethyl (3-formylphenyl) carbonate 在 Oxone 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以63%的产率得到3-ethoxycarbonyloxybenzoic acid
  参考文献：
  名称：

  Crystal Structure of the Homo sapiens Kynureninase-3-Hydroxyhippuric Acid Inhibitor Complex: Insights into the Molecular Basis Of Kynureninase Substrate Specificity

  摘要：

  Homo sapiens kynureninase is a pyridoxal-5'-phosphate dependent enzyme that catalyzes the hydrolytic cleavage of 3-hydroxykynurenine to yield 3-hydroxyanthranilate and L-alanine as part of the tryptophan catabolic pathway leading to the de novo biosynthesis of NAD(+). This pathway results in quinolinate, an excitotoxin that is an NMDA receptor agonist. High levels of quinolinate have been correlated with the etiology of neurodegenerative disorders such as AIDS-related dementia and Alzheimer's disease. We have synthesized a novel kynureninase inhibitor, 3-hydroxyhippurate, cocrystallized it with human kynureninase, and solved the atomic structure. On the basis of an analysis of the complex, we designed a series of His-102, Ser-332, and Asn-333 mutants. The H102W/N333T and H102W/S332G/N333T mutants showed complete reversal of substrate specificity between 3-hydroxykynurenine and L-kynurenine, thus defining the primary residues contributing to substrate specificity in kynureninases.

  DOI：

  10.1021/jm8010806

文献信息

• Preparation of fluorine-containing diphenyl ethers
  申请人：Imperial Chemical Industries Limited

  公开号：US04384135A1

  公开（公告）日：1983-05-17

  A method of preparing a diphenyl ether compound of the formula (II) ##STR1## wherein X is F, Cl or Br; Z is hydrogen, halogen, NO.sub.2 of CN; and W is methyl, cyano, CH.sub.3 CO--, or a group --C--OR, wherein R is --OH; --OM wherein M is a cation; OR.sup.1 wherein R.sup.1 is an optionally substituted aliphatic radical; --NR.sup.2 R.sup.3 wherein R.sup.2 and R.sup.3 are each hydrogen or an optionally substituted aliphatic radical; or --NHSO.sub.2 R.sup.4 wherein R.sup.4 is alkyl of 1 to 6 carbon atoms, which comprises reacting a 3-X-substituted-4,5-difluorobenzotrifluoride with a salt of a 3,4-W,Z-substituted phenol. The invention further comprises novel 3-X-4,5-difluorobenzotrifluorides for use in the process.

  一种制备二苯醚化合物的方法，其化学式为（II）##STR1## 其中X为F，Cl或Br；Z为氢，卤素，NO.sub.2或CN；W为甲基，氰基，CH.sub.3CO--或--C--OR基团，其中R为--OH；--OM，其中M为阳离子；OR.sup.1其中R.sup.1为可选取代的脂肪基；--NR.sup.2R.sup.3其中R.sup.2和R.sup.3分别为氢或可选取代的脂肪基；或--NHSO.sub.2R.sup.4其中R.sup.4为1至6个碳原子的烷基。该方法包括将3-X-取代-4,5-二氟苯基三氟甲苯与3,4-W，Z-取代酚的盐反应。该发明还包括用于该过程的新型3-X-4,5-二氟苯基三氟甲苯。
• Daniel; Nierenstein, Chemische Berichte, 1911, vol. 44, p. 703
  作者：Daniel、Nierenstein

  DOI：——

  日期：——
• Method of preparing fluorine-substituted diphenyl ether derivatives and fluorine-substituted halogeno benzene derivatives for use therein
  申请人：IMPERIAL CHEMICAL INDUSTRIES PLC

  公开号：EP0034402B1

  公开（公告）日：1984-08-29
• US4384135A
  申请人：——

  公开号：US4384135A

  公开（公告）日：1983-05-17
• Crystal Structure of the <i>Homo sapiens</i> Kynureninase-3-Hydroxyhippuric Acid Inhibitor Complex: Insights into the Molecular Basis Of Kynureninase Substrate Specificity
  作者：Santiago Lima、Sunil Kumar、Vijay Gawandi、Cory Momany、Robert S. Phillips

  DOI：10.1021/jm8010806

  日期：2009.1.22

  Homo sapiens kynureninase is a pyridoxal-5'-phosphate dependent enzyme that catalyzes the hydrolytic cleavage of 3-hydroxykynurenine to yield 3-hydroxyanthranilate and L-alanine as part of the tryptophan catabolic pathway leading to the de novo biosynthesis of NAD(+). This pathway results in quinolinate, an excitotoxin that is an NMDA receptor agonist. High levels of quinolinate have been correlated with the etiology of neurodegenerative disorders such as AIDS-related dementia and Alzheimer's disease. We have synthesized a novel kynureninase inhibitor, 3-hydroxyhippurate, cocrystallized it with human kynureninase, and solved the atomic structure. On the basis of an analysis of the complex, we designed a series of His-102, Ser-332, and Asn-333 mutants. The H102W/N333T and H102W/S332G/N333T mutants showed complete reversal of substrate specificity between 3-hydroxykynurenine and L-kynurenine, thus defining the primary residues contributing to substrate specificity in kynureninases.