methyl 1-hydroxy-7-methoxy-2-naphthalenecarboxylate | 95271-70-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: methyl 1-hydroxy-7-methoxy-2-naphthalenecarboxylate
• 英文别名: methyl 1-hydroxy-7-methoxy-2-naphthoate；methyl 1-hydroxy-7-methoxynaphthalene-2-carboxylate；1-hydroxy-7-methoxy-2-naphthalenecarboxylic acid, methyl ester
• CAS: 95271-70-8
• 化学式: C₁₃H₁₂O₄
• 分子量: 232.236
• InChiKey: WGRQAMACYMSQLH-UHFFFAOYSA-N

物化性质

• 熔点：
  81-82 °C
• 沸点：
  369.2±22.0 °C(Predicted)
• 密度：
  1.262±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 1-hydroxy-7-methoxy-2-naphthalenecarboxylate 在 氢氧化钾 、 potassium tert-butylate 、 N,N'-羰基二咪唑 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 反应 14.25h， 生成 1-Isopropoxy-7-methoxy-naphthalene-2-carboxylic acid (1H-tetrazol-5-yl)-amide
  参考文献：
  名称：

  Novel benzothiophene-, benzofuran-, and naphthalenecarboxamidotetrazoles as potential antiallergy agents

  摘要：

  The synthesis and antiallergic activity of a series of novel benzothiophene-, benzofuran-, and naphthalenecarbox-amidotetrazoles are described. A number of the compounds inhibit the release of histamine from anti-IgE stimulated basophils obtained from allergic donors. Optimal inhibition is exhibited in benzothiophenes with a 3-alkoxy substituent in combination with a 5-methoxy, 6-methoxy, or a 5,6-dimethoxy group. Compounds 13c (CI-959) also inhibited respiratory burst of human neutrophils and the release of mediators from anti-IgE-stimulated human chopped lung.

  DOI：

  10.1021/jm00083a023
• 作为产物：
  描述：

  methyl 1,2,3,4-tetrahydro-2-bromo-7-methoxy-1-oxo-2-naphthalenecarboxylate 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 以54%的产率得到methyl 1-hydroxy-7-methoxy-2-naphthalenecarboxylate
  参考文献：
  名称：

  Novel benzothiophene-, benzofuran-, and naphthalenecarboxamidotetrazoles as potential antiallergy agents

  摘要：

  The synthesis and antiallergic activity of a series of novel benzothiophene-, benzofuran-, and naphthalenecarbox-amidotetrazoles are described. A number of the compounds inhibit the release of histamine from anti-IgE stimulated basophils obtained from allergic donors. Optimal inhibition is exhibited in benzothiophenes with a 3-alkoxy substituent in combination with a 5-methoxy, 6-methoxy, or a 5,6-dimethoxy group. Compounds 13c (CI-959) also inhibited respiratory burst of human neutrophils and the release of mediators from anti-IgE-stimulated human chopped lung.

  DOI：

  10.1021/jm00083a023

文献信息

• N-1H-tetrazol-5-yl-2-naphthalene carboxamides and their use as
  申请人：Warner-Lambert Company

  公开号：US04767776A1

  公开（公告）日：1988-08-30

  Novel naphthalene derivatives having antiallergy and antiinflammatory activity.

  具有抗过敏和抗炎活性的新萘衍生物。
• Solvent-Free Synthesis of Salen Ligands and Pd(II)– and Cu(II)–Salen Complexes: Their Use in the Oxidation of α-Tetralones to α-Naphthols
  作者：José Cívicos、Juliana Coimbra、Paulo Costa

  DOI：10.1055/s-0036-1588446

  日期：2017.9

  trans-cyclohexane-1,2-diamine was allowed to react with eleven aldehydes with different patterns of substitution at the aromatic ring, in the absence of solvent, by manually milling the reagents. The corresponding imines were obtained in moderated to high chemical yields, in only 10 minutes of reaction. A one-pot, two-step preparation of stable complexes of selected imines with Pd(OAc)2 and Cu(OAc)2

  摘要 在不存在溶剂的情况下，通过手动研磨试剂，使外消旋的反式-环己烷-1，2-二胺与十一种在芳香环上具有不同取代方式的醛反应。在仅10分钟的反应中，以中等到高的化学产率获得了相应的亚胺。一锅两步制备选定的亚胺与Pd（OAc）2和Cu（OAc）2的稳定配合物，并将这些配合物用作甲基1-氧代-1,2,3芳构化的催化剂，还报道了4-四氢萘-2-羧酸酯为相应的1-羟基萘-2-羧酸甲酯。 在不存在溶剂的情况下，通过手动研磨试剂，使外消旋的反式-环己烷-1，2-二胺与十一种在芳香环上具有不同取代方式的醛反应。在仅10分钟的反应中，以中等到高的化学产率获得了相应的亚胺。一锅两步制备选定的亚胺与Pd（OAc）2和Cu（OAc）2的稳定配合物，并将这些配合物用作甲基1-氧代-1,2,3芳构化的催化剂，还报道了4-四氢萘-2-羧酸酯为相应的1-羟基萘-2-羧酸甲酯。
• Copper- versus palladium-catalyzed aromatization of 2-(methoxycarbonyl) tetralones: synthesis of methyl 1-hydroxy-2-naphthoates
  作者：José F. Cívicos、Carlos M.R. Ribeiro、Paulo R.R. Costa、Carmen Nájera

  DOI：10.1016/j.tet.2016.01.057

  日期：2016.4

  at the β-position by an ester group is reported using either CuI or Pd2(dba)3. In the case of using CuI (10 mol %) as catalyst and Cs2CO3 as base in dioxane, 2-(methoxycarbonyl)-α-tetralones are smoothly converted into the corresponding methyl 1-hydroxy-2-naphthoates at 70 °C under air. Alternatively, Pd2(dba)3 (1.25 mol %) can also be used as catalyst in the presence of K3PO4 as base in toluene also

  使用CuI或Pd 2（dba）3报道了在β位被酯基取代的α-四氢萘酮的芳构化。在二恶烷中使用CuI（10 mol％）作为催化剂和Cs 2 CO 3作为碱的情况下，在70°C下将2-（甲氧基羰基）-α-四氢萘酮平稳地转化为相应的1-羟基-2-萘甲酸甲酯在空气中。或者，在K 3 PO 4的存在下，也可以将Pd 2（dba）3（1.25 mol％）用作催化剂。也是在70°C氩气下在甲苯中作为碱。这些是将这些类型的α-四氢萘酮进行芳构化的最直接方法。由于更高的效率，经济和实用的原因，CuI是选择的催化剂。
• Novel thermal rearrangement of 1-alkoxycarbonyl-2-aryl-cyclopropanes
  作者：Miguel E. Alonso、A. Wladimir Chitty、Sarah Pekerar、Mar�a de L. Borgo

  DOI：10.1039/c39840001542

  日期：——

  with either one acyl and one alkoxycarbonyl or two alkoxycarbonyl groups on C-1 yield 2-carbonyl-1-naphthol derivatives upon thermolysis at temperatures in the range 210–340 °C in an unprecedented rearrangement of the cyclopropane ring.

  C-1上被一个酰基和一个烷氧羰基或两个烷氧羰基取代的2-芳基环丙烷在210-340°C的温度下以前所未有的重排环丙烷温度进行热解时，会生成2-羰基-1-萘酚衍生物。
• Identification of First-in-Class Inhibitors of Kallikrein-Related Peptidase 6 That Promote Oligodendrocyte Differentiation
  作者：Sabrina Aït Amiri、Cyrille Deboux、Feryel Soualmia、Nancy Chaaya、Maxime Louet、Eric Duplus、Sandrine Betuing、Brahim Nait Oumesmar、Nicolas Masurier、Chahrazade El Amri

  DOI：10.1021/acs.jmedchem.0c02175

  日期：2021.5.13