methyl 5,8-dimethoxy-1-naphthoate | 127536-34-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: methyl 5,8-dimethoxy-1-naphthoate
• 英文别名: methyl 5,8-dimethoxynaphthalene-1-carboxylate
• CAS: 127536-34-9
• 化学式: C₁₄H₁₄O₄
• 分子量: 246.263
• InChiKey: BCAWDISSJPVXDN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 5,8-dimethoxy-1-naphthoate 在 sodium hydroxide 作用下， 以 水 为溶剂， 生成 5,8-dimethoxy-1-naphthoic acid
  参考文献：
  名称：

  5,8-Dimethoxy-1-naphthoic Acid and Methyl 5,8-Dimethoxy-1-naphthoate

  摘要：

  In 5,8-dimethoxy-1-naphthoic acid, C13H12O4, hydrogen bonding is of the cyclic dimer type. The acid H atom is modelled as being distributed equally over two sites. In addition to the conventional hydrogen bonds, there are three significantly attractive C-H . . . O interactions. The dihedral angle between the naphthalene core plane and the carboxyl plane is 80.0 (1)degrees. In methyl 5,8-dimethoxy-1-naphthoate, C14H14O4, there are no conventional hydrogen bonds but there are three significantly attractive C-H . . . O interactions. With the exception of the C-O distances in the carboxyl groups, the molecular geometries of the acid and the ester are quite similar.

  DOI：

  10.1107/s0108270197004940
• 作为产物：
  描述：

  1,4-二甲氧基萘 、 硫酸二甲酯 、 叔丁基锂 、 二氧化碳 以50%的产率得到
  参考文献：
  名称：

  NEWMAN, MELVIN S.;CHOUDHARY, ANIL R., ORG. PREP. AND PROCED. INT., 21,(1989) N, C. 359-360

  摘要：

  DOI：

文献信息

• Rhodium-catalyzed C-H bond activation for the synthesis of quinonoid compounds: Significant Anti-Trypanosoma cruzi activities and electrochemical studies of functionalized quinones
  作者：Guilherme A.M. Jardim、Thaissa L. Silva、Marilia O.F. Goulart、Carlos A. de Simone、Juliana M.C. Barbosa、Kelly Salomão、Solange L. de Castro、John F. Bower、Eufrânio N. da Silva Júnior

  DOI：10.1016/j.ejmech.2017.05.011

  日期：2017.8

  synthesized by rhodium-catalyzed C-H bond activation and palladium-catalyzed cross-coupling reactions, were evaluated against bloodstream trypomastigotes of T. cruzi. We have identified fifteen compounds with IC50/24 h values of less than 2 μM. Electrochemical studies on A-ring functionalized naphthoquinones were also performed aiming to correlate redox properties with trypanocidal activity. For instance

  通过铑催化的CH键活化和钯催化的交叉偶联反应合成的三十四个含卤素和硒的醌，对克氏锥虫的血色伪鞭毛体进行了评估。我们确定了15种化合物的IC 50/24 h值小于2μM。还进行了A环官能化萘醌的电化学研究，旨在将氧化还原特性与锥虫杀灭活性联系起来。例如（E）-5-styryl-1,4-naphthoquinone 59和5,8-diiodo-1,4-naphthoquinone 3其潜在活性是标准药物苯甲硝唑的约50倍，是有待进一步研究的潜在衍生物。这些化合物代表了在南美锥虫病治疗中有用的强大新药。
• NEWMAN, MELVIN S.;CHOUDHARY, ANIL R., ORG. PREP. AND PROCED. INT., 21,(1989) N, C. 359-360
  作者：NEWMAN, MELVIN S.、CHOUDHARY, ANIL R.

  DOI：——

  日期：——
• 5,8-Dimethoxy-1-naphthoic Acid and Methyl 5,8-Dimethoxy-1-naphthoate
  作者：A. C. Blackburn、R. E. Gerkin

  DOI：10.1107/s0108270197004940

  日期：1997.8.15

  In 5,8-dimethoxy-1-naphthoic acid, C13H12O4, hydrogen bonding is of the cyclic dimer type. The acid H atom is modelled as being distributed equally over two sites. In addition to the conventional hydrogen bonds, there are three significantly attractive C-H . . . O interactions. The dihedral angle between the naphthalene core plane and the carboxyl plane is 80.0 (1)degrees. In methyl 5,8-dimethoxy-1-naphthoate, C14H14O4, there are no conventional hydrogen bonds but there are three significantly attractive C-H . . . O interactions. With the exception of the C-O distances in the carboxyl groups, the molecular geometries of the acid and the ester are quite similar.