1-hydroxy-2-naphthoate | 776-48-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-hydroxy-2-naphthoate
• 英文别名: 2-carboxynaphthalen-1-olate
• CAS: 776-48-7
• 化学式: C₁₁H₇O₃
• 分子量: 187.175
• InChiKey: SJJCQDRGABAVBB-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  60.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Boc-L-prolyl 、 1-hydroxy-2-naphthoate 在 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Novel Chiral Secondary Amine-Amide Catalysts Friedel-Craft Alkylation Reaction

  摘要：

  开发了一种高效的催化不对称Friedel-Crafts烷基化反应，使用新型的手性二级胺-酰胺作为催化剂对吲哚与硝基烯烃进行了反应。获得了多种类型的硝基烷基化吲哚，产率极佳（81-93%），且具有高的对映选择性（最高可达95% ee）。

  DOI：

  10.14233/ajchem.2017.20269

文献信息

• 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。
• Biodegradation of phenanthrene by Alcaligenes  sp. strain PPH: partial purification and characterization of 1-hydroxy-2-naphthoic acid hydroxylase
  作者：Jaigeeth Deveryshetty、Prashant S. Phale

  DOI：10.1111/j.1574-6968.2010.02079.x

  日期：2010.10

  PPH degrades phenanthrene via 1-hydroxy-2-naphthoic acid (1-H2NA), 1,2-dihydroxynaphthalene (1,2-DHN), salicylic acid and catechol. Enzyme activity versus growth profile and heat stability studies suggested the presence of two distinct hydroxylases, namely 1-hydroxy-2-naphthoic acid hydroxylase and salicylate hydroxylase. 1-Hydroxy-2-naphthoic acid hydroxylase was partially purified (yield 48%, fold

  产碱菌 PPH菌株通过1-羟基-2-萘甲酸（1-H2NA），1,2-二羟基萘（1,2-DHN），水杨酸和邻苯二酚降解菲。酶活性对生长曲线和热稳定性的研究表明存在两种不同的羟化酶，即1-羟基-2-萘甲酸羟化酶和水杨酸羟化酶。1-羟基-2-萘甲酸羟化酶被部分纯化（收率48％，倍数81），被发现是同二聚体，亚基分子量约为34 kDa。该酶为黄色，在274、375和445 nm处显示紫外线可见吸收最大值，而在527 nm处的荧光发射最大值表明它是黄素蛋白。通过酸-硫酸铵（2 M）渗析法制备的脱辅酶无色，用FAD复溶后失去活性并失去了特征性的黄素吸收光谱，但恢复了约90％的活性。修复基团的提取和通过HPLC的分析表明，全酶含有FAD。该酶对1-H2NA具有特异性，对其他任何羟基萘甲酸类似物或水杨酸均无活性。在存在NADPH或NADH的情况下，1-H2NA的K（m）保持不变（分别为72和75μM），表
• A catabolic pathway for the degradation of chrysene by Pseudoxanthomonas sp. PNK-04
  作者：Anand S. Nayak、Sanganal Sanjeev Kumar、Mudde Santosh Kumar、Oblesha Anjaneya、Timmanagouda B. Karegoudar

  DOI：10.1111/j.1574-6968.2011.02301.x

  日期：2011.7

  The chrysene-degrading bacterium Pseudoxanthomonas sp. PNK-04 was isolated from a coal sample. Three novel metabolites, hydroxyphenanthroic acid, 1-hydroxy-2-naphthoic acid and salicylic acid, were identified by TLC, HPLC and MS. Key enzyme activities, namely 1-hydroxy-2-naphthoate hydroxylase, 1,2-dihydroxynaphthalene dioxygenase, salicylaldehyde dehydrogenase and catechol-1,2-dioxygenase, were noted in the cell-free extract. These results suggest that chrysene is catabolized via hydroxyphenanthroic acid, 1-hydroxy-2-naphthoic acid, salicylic acid and catechol. The terminal aromatic metabolite, catechol, is then catabolized by catechol-1,2-dioxygenase to cis,cis-muconic acid, ultimately forming TCA cycle intermediates. Based on these studies, the proposed catabolic pathway for chrysene degradation by strain PNK-04 is chrysene → hydroxyphenanthroic acid → 1-hydroxy-2-naphthoic acid → 1,2-dihydroxynaphthalene → salicylic acid → catechol →cis,cis-muconic acid.

  煤样中分离出一种可降解屈的细菌——假黄单胞菌（Pseudoxanthomonas sp. PNK-04）。通过薄层色谱法（TLC）、高效液相色谱法（HPLC）和质谱法（MS）鉴定出三种新型代谢产物：羟基菲酸、1-羟基-2-萘酸和水杨酸。在无细胞提取物中检测到1-羟基-2-萘酸羟化酶、1,2-二羟基萘双加氧酶、水杨醛脱氢酶和儿茶酚-1,2-双加氧酶等关键酶活性。这些结果表明，屈通过羟基菲酸、1-羟基-2-萘酸、水杨酸和儿茶酚进行代谢。最终，芳香族代谢产物儿茶酚通过儿茶酚-1,2-双加氧酶代谢为顺式-顺式-穆孔酸，最终形成TCA循环的中间产物。根据这些研究，PNK-04菌株降解屈的代谢途径为：屈→羟基菲酸→1-羟基-2-萘酸→1,2-二羟基萘→水杨酸→儿茶酚→顺式-顺式-穆
• Novel Chiral Secondary Amine-Amide Catalysts Friedel-Craft Alkylation Reaction
  作者：Kejun Huang、Xuehai Pei、Xiaogang Yin、Zhiming Chen

  DOI：10.14233/ajchem.2017.20269

  日期：——

  A highly efficient catalytic asymmetric Friedel-Crafts alkylation of indole with nitroalkenes using novel chiral secondary amine-amide as catalyst has been developed. Various types of nitroalkylated indoles were obtained in excellent yields (81-93 %) and high enantio-selectivities (up to 95 % ee).

  开发了一种高效的催化不对称Friedel-Crafts烷基化反应，使用新型的手性二级胺-酰胺作为催化剂对吲哚与硝基烯烃进行了反应。获得了多种类型的硝基烷基化吲哚，产率极佳（81-93%），且具有高的对映选择性（最高可达95% ee）。