2-甲酰基苯甲酸阴离子 | 58502-59-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-甲酰基苯甲酸阴离子
• 英文名称: 2-formylbenzoic acid anion
• 英文别名: 2-formyl-benzoic acid; deprotonated form；2-formyl-benzoic acid anion；2-Formylbenzoate
• CAS: 58502-59-3
• 化学式: C₈H₅O₃
• 分子量: 149.126
• InChiKey: DYNFCHNNOHNJFG-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  57.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-甲酰基苯甲酸阴离子 、 potassium carbonate 、 溴甲苯 在 水 、 氯化钠 、 Sodium sulfate-III 作用下， 以 N,N-二甲基甲酰胺 、 乙酸乙酯 为溶剂， 反应 2.0h， 以to give the title compound (795 mg; yield, 99%) as a colorless oily substance的产率得到benzyl 2-formylbenzoate
  参考文献：
  名称：

  AMIDE DERIVATIVE

  摘要：

  本发明提供了化合物或其药理学上可接受的盐。在各种实施例中，这些化合物对神经激肽NK1受体、神经激肽NK2受体和毒蕈碱M3受体具有拮抗作用。这些化合物可用作治疗支气管哮喘、慢性阻塞性肺疾病等疾病的治疗剂。

  公开号：

  US20120071467A1
• 作为产物：
  描述：

  benzocyclobutene-1,2-dione 在 水 、 hydroxide 、 sodium chloride 作用下， 以 二甲基亚砜 为溶剂， 生成 2-甲酰基苯甲酸阴离子
  参考文献：
  名称：

  Reactions of carbonyl compounds in basic solutions. Part 24.1 The mechanism of the base-catalysed ring fission of substituted benzocyclobutene-1,2-diones

  摘要：

  在25.0和60.0°C下，测定了水溶液中一系列取代苯并环丁二烯二酮在碱催化开环反应中生成相应2-甲酰基苯甲酸的速率系数。使用改进的哈米特方程，对4-取代基和4,5-二取代基对速率的影响进行了关联，计算出反应常数ρ在25.0°C时约为3.6。计算了活化参数。研究了溶剂组成对速率的影响。还研究了动力学溶剂同位素效应、产物组成和在18O富集水中的富集情况。所有证据表明，反应机制是通过羟基离子对二酮的快速可逆加成，随后分子内亲核攻击第二个羰基，形成碳负离子中间体。

  DOI：

  10.1039/a606310a

文献信息

• Reactions of carbonyl compounds in basic solutions. Part 13. The mechanism of the alkaline hydrolysis of 3-(3-substituted phenoxy)phthalides, -3-methyl-phthalides, -3-phenylphthalides, naphthalides, -3-phenylnaphthalides, and phenanthralides, and of 3-substituted 3-methoxyphthalides
  作者：Fredrick Anvia、Keith Bowden、Faiq A. El Kaissi、Victoria Saez

  DOI：10.1039/p29900001809

  日期：——

  effects of substitution on the phenoxy esters have been assessed by means of, the Hammett equation. The results for the methyl esters are related to the steric effect of substituents using the Taft equation. All the pseudo-esters are hydrolysed with rate-determining attack by hydroxide anion at the carbonyl group, followed by rapid ring fission to form the carboxylate anion of the corresponding acid as the

  已经测量了在30.0和50.0°C下对3-（3-取代苯氧基）邻苯二甲酸酯，-3-甲基邻苯二甲酸酯，-3-苯基邻苯二甲酸酯，萘二甲酸酯，-3-苯基萘二甲酸酯和邻苯二甲酰胺进行碱水解的速率系数，伪-2-酰基苯甲酸甲酯在70％（v / v）的二恶烷水溶液中处于多个温度下。已经评估了激活的焓和熵。已经通过哈米特方程评估了取代对苯氧基酯的影响。使用Taft方程，甲酯的结果与取代基的空间效应有关。所有的拟酯均被羰基上的氢氧根阴离子水解，以决定速率的方式进行水解，然后迅速发生环裂变，形成相应酸的羧酸根阴离子。在六个系列的苯基假酯的整个范围内都没有显示出反应性-选择性。根据过渡态的结构以及影响反应性的空间，立体化学和极性因素讨论了这些结果。
• Amide derivative
  申请人：Ikeda Takuya

  公开号：US08476253B2

  公开（公告）日：2013-07-02

  Compounds or pharmacologically acceptable salts thereof are provided. In various embodiments the compounds have an antagonistic effect on a neurokinin NK1 receptor, a neurokinin NK2 receptor, and a muscarine M3 receptor. The compounds are useful as therapeutic agents for bronchial asthma, chronic obstructive pulmonary disease, or the like.

  本发明提供了化合物或其药理学上可接受的盐。在各种实施例中，这些化合物具有对神经激肽NK1受体、神经激肽NK2受体和肌碱M3受体的拮抗作用。这些化合物可用作治疗支气管哮喘、慢性阻塞性肺疾病或类似疾病的治疗剂。
• Phthalate pathway of phenanthrene metabolism: formation of 2'-carboxybenzalpyruvate
  作者：E A Barnsley

  DOI：10.1128/jb.154.1.113-117.1983

  日期：1983.4

  The metabolism of phenanthrene by a gram-negative organism able to use this compound as a sole source of carbon and energy has been examined. 1-Hydroxy-2-naphthoic acid was oxidized by oxygen in a reaction catalyzed by a dioxygenase which was activated by ferrous ions. The stoichiometry of the oxidation and the UV spectrum of the product were consistent with the identification of the product as 2'-carboxybenzalpyruvate. This was confirmed by cleaving the product with a partially purified aldolase to yield 2-carboxybenzaldehyde and pyruvate. A number of enzymes for the metabolism of 1-hydroxy-2-naphthoic acid were induced by growth on phthalate or (less well) by growth on protocatechuate. The latter supported only a slow rate of growth, and this and poor induction may have been due to a slow rate of entry into the cell.

  翻译结果： 研究了一种革兰氏阴性细菌对菲的代谢，该细菌能够将菲作为唯一的碳和能源来源。1-羟基-2-萘甲酸在铁离子激活的二氧化酶催化下被氧气氧化。氧化的化学计量和产物的紫外光谱与2'-羧基苯丙酮酸的鉴定一致。用部分纯化的醛缩酶裂解产物，得到2-羧基苯甲醛和丙酮，证实了产物的鉴定。在邻苯二甲酸或邻苯二酚生长时，诱导了一些代谢1-羟基-2-萘甲酸的酶。后者只支持缓慢的生长速率，这可能是由于进入细胞的速率缓慢，诱导不良造成的。
• Biochemical and Genetic Characterization of <i>trans</i> -2′-Carboxybenzalpyruvate Hydratase-Aldolase from a Phenanthrene-Degrading <i>Nocardioides</i> Strain
  作者：Tokuro Iwabuchi、Shigeaki Harayama

  DOI：10.1128/jb.180.4.945-949.1998

  日期：1998.2.15

  trans -2′-Carboxybenzalpyruvate hydratase-aldolase was purified from a phenanthrene-degrading bacterium, Nocardioides sp. strain KP7, and characterized. The purified enzyme was found to have molecular masses of 38 kDa by sodium dodecyl sulfate-polyacrylamide gel electrophoresis and 113 kDa by gel filtration chromatography. Thus, the homotrimer of the 38-kDa subunit constituted an active enzyme. The K _m and k cat values of this enzyme for trans -2′-carboxybenzalpyruvate were 50 μM and 13 s ⁻¹ , respectively. trans -2′-Carboxybenzalpyruvate was transformed to 2-carboxybenzaldehyde and pyruvate by the action of this enzyme. The structural gene for this enzyme was cloned and sequenced; the length of this gene was 996 bp. The deduced amino acid sequence of this enzyme exhibited homology to those of trans -2′-hydroxybenzalpyruvate hydratase-aldolases from Pseudomonas putida PpG7 and Pseudomonas sp. strain C18.

  摘要 反式 -从一种菲类降解细菌中纯化出了-2′-羧基苯丙酮酸水解酶-醛酸酶、 Nocardioides sp.菌株 KP7 中纯化了菲降解菌 Nocardioides sp.通过十二烷基硫酸钠-聚丙烯酰胺凝胶电泳发现，纯化后的酶的分子质量为 38 kDa，通过凝胶过滤层析发现，纯化后的酶的分子质量为 113 kDa。因此，38 kDa 亚基的同源三聚体构成了一种活性酶。其 K m 和 k cat 值。 反式 -2′-羧基苯丙酮酸的 k cat 值分别为 50 μM 和 13 s -1 的 k cat 值分别为 50 μM 和 13 s -1。 反式 -2′-羧基苯丙酮酸在这种酶的作用下转化为 2-羧基苯甲醛和丙酮酸。该酶的结构基因已被克隆并测序，其长度为 996 bp。该酶的氨基酸序列推断与 反式 -2′-hydroxybenzalpyruvate hydratase-aldolases from 假单胞菌 PpG7 和 假单胞菌 菌株 C18.
• Biochemical and genetic characterization of 2-carboxybenzaldehyde dehydrogenase, an enzyme involved in phenanthrene degradation by Nocardioides sp. strain KP7
  作者：T Iwabuchi、S Harayama

  DOI：10.1128/jb.179.20.6488-6494.1997

  日期：1997.10

  2-Carboxybenzaldehyde dehydrogenase from the phenanthrene-degrading bacterium Nocardioides sp. strain KP7 was purified and characterized. The purified enzyme had a molecular mass of 53 kDa by sodium dodecyl sulfate-polyacrylamide gel electrophoresis and 205 kDa by gel filtration chromatography. Thus, the homotetramer of the 53-kDa subunit constituted an active enzyme. The apparent Km and kcat values of this enzyme for 2-carboxybenzaldehyde were 100 microM and 39 s(-1), respectively, and those for NAD+ were 83 microM and 32 s(-1), respectively. The structural gene for this enzyme was cloned and sequenced. The length of the gene was 1,455 bp. The nucleotide sequence of the 10,279 bp of DNA around the gene for 2-carboxybenzaldehyde dehydrogenase was also determined, and seven open reading frames were found in this DNA region. These were the genes for 1-hydroxy-2-naphthoate dioxygenase (phdI) and trans-2'-carboxybenzalpyruvate aldolase (phdJ), orf1, the gene for 2-carboxybenzaldehyde dehydrogenase (phdK), orf2/orf3, and orf4. The amino acid sequence of the orf1 product was similar to that of the aromatic hydrocarbon transporter gene (pcaK) in Pseudomonas putida PRS2000. The amino acid sequence of the orf4 product revealed a similarity to cytochrome P-450 proteins. The region between phdK and orf4 encoded orf2 and orf3 on different strands. The amino acid sequences of the orf2 and orf3 products exhibited no significant similarity to the reported sequences in protein databases.

  从苯并降解细菌Nocardioides sp.菌株KP7中纯化和表征了2-羧基苯甲醛脱氢酶。纯化的酶在SDS-PAGE和凝胶过滤色谱中的分子量分别为53 kDa和205 kDa。因此，53 kDa亚基的同源四聚体构成了活性酶。该酶对2-羧基苯甲醛的表观Km和kcat值分别为100微米和39 s（-1），对NAD +的表观Km和kcat值分别为83微米和32 s（-1）。该酶的结构基因被克隆并测序。基因长度为1,455 bp。还确定了2-羧基苯甲醛脱氢酶基因周围10,279 bp的DNA序列，并在该DNA区域中发现了七个开放阅读框架。这些是1-羟基-2-萘酸双氧酶（phdI）和trans-2'-羧基苯丙酮醛缩酮酶（phdJ）的基因，orf1，2-羧基苯甲醛脱氢酶（phdK）的基因，orf2 / orf3和orf4。orf1产物的氨基酸序列类似于假单胞菌Pseudomonas putida PRS2000中的芳香烃转运蛋白基因（pcaK）。orf4产物的氨基酸序列显示与细胞色素P-450蛋白相似。 phdK和orf4之间的区域在不同链上编码orf2和orf3。orf2和orf3产物的氨基酸序列在蛋白质数据库中没有显着的相似性。