8-氯萘-2-羧酸乙酯 | 95361-03-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 8-氯萘-2-羧酸乙酯
• 英文名称: ethyl 8-chloro-2-naphthylformate
• 英文别名: 8-chloro-[2]naphthoic acid ethyl ester；8-Chlor-[2]naphthoesaeure-aethylester；Ethyl 8-chloronaphthalene-2-carboxylate
• CAS: 95361-03-8
• 化学式: C₁₃H₁₁ClO₂
• 分子量: 234.682
• InChiKey: KKPFRPLZEYRDCU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  16
• 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：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  8-氯萘-2-羧酸乙酯 在 亚磷酸三苯酯 、 盐酸 、 sodium hydroxide 、 甲酸 、 sodium paraperiodate 、 N,O-双(三甲基硅烷基)三氟乙酰胺 、 氯 、 sodium hydride 、 锌 作用下， 以 甲醇 、 甲酸 、 二氯甲烷 、 水 、 乙酸酐 、 N,N-二甲基甲酰胺 为溶剂， 反应 26.75h， 生成 (R)-7-<(8-chloro-2-naphthyl)acetamido>-3-methyl-3-cephem-4-carboxylic acid
  参考文献：
  名称：

  Orally absorbable cephalosporin antibiotics. 1. Structure-activity relationships of benzothienyl- and naphthylglycine derivatives of 7-aminodeacetoxycephalosporanic acid

  摘要：

  A structure-activity relationship study of a number of orally absorbed cephalosporins together with their syntheses is described. These new cephalosporins are benzothienyl- and naphthylglycine derivatives of 7-aminodeacetoxycephalosporanic acid. Several different synthetic methods for the glycine side chains, their protection, and the final acylations are reported. Several of these analogues were more active than cephalexin both in vitro and in vivo against commonly encountered Gram-positive bacteria. (R)-7-(3-Benzothienylglycylamido)-3-methyl-3-cephem-4-carboxylic acid (1R) has emerged as a potent antibacterial agent and is currently undergoing preclinical evaluation.

  DOI：

  10.1021/jm00150a022
• 作为产物：
  描述：

  8-氨基-2-萘甲酸 在 盐酸 作用下， 生成 8-氯萘-2-羧酸乙酯
  参考文献：
  名称：

  Ekstrand, Journal fur praktische Chemie (Leipzig 1954), 1891, vol. <2> 43, p. 427

  摘要：

  DOI：

文献信息

• Naphthylglycyl cephalosporin derivatives
  申请人：Eli Lilly and Company

  公开号：US04490370A1

  公开（公告）日：1984-12-25

  Naphthylglycyl and tetrahydronaphthylglycyl cephalosporins are potent antibacterial agents and are particularly useful as oral treatments for upper respiratory infections.

  Naphthylglycyl和tetrahydronaphthylglycyl头孢菌素是强效的抗菌剂，特别适用于口服治疗上呼吸道感染。
• Improvements in or relating to naphthylglycyl cephalosporin derivatives
  申请人：ELI LILLY AND COMPANY

  公开号：EP0122155A2

  公开（公告）日：1984-10-17

  Naphthylglycyl and tetrahydronaphthylglycyl cephalosporins are potent antibacterial agents and particularly useful in the oral treatment of upper respiratory infections.

  萘乙酰基和四氢萘乙酰基头孢菌素是强效抗菌剂，尤其适用于口服治疗上呼吸道感染。
• US4490370A
  申请人：——

  公开号：US4490370A

  公开（公告）日：1984-12-25
• Orally absorbable cephalosporin antibiotics. 1. Structure-activity relationships of benzothienyl- and naphthylglycine derivatives of 7-aminodeacetoxycephalosporanic acid
  作者：Stjepan Kukolja、Susan E. Draheim、Janice L. Pfeil、Robin D. G. Cooper、Bernard J. Graves、Richard E. Holmes、David A. Neel、George W. Huffman、J. Alan Webber

  DOI：10.1021/jm00150a022

  日期：1985.12

  A structure-activity relationship study of a number of orally absorbed cephalosporins together with their syntheses is described. These new cephalosporins are benzothienyl- and naphthylglycine derivatives of 7-aminodeacetoxycephalosporanic acid. Several different synthetic methods for the glycine side chains, their protection, and the final acylations are reported. Several of these analogues were more active than cephalexin both in vitro and in vivo against commonly encountered Gram-positive bacteria. (R)-7-(3-Benzothienylglycylamido)-3-methyl-3-cephem-4-carboxylic acid (1R) has emerged as a potent antibacterial agent and is currently undergoing preclinical evaluation.
• Ekstrand, Journal fur praktische Chemie (Leipzig 1954), 1891, vol. <2> 43, p. 427
  作者：Ekstrand

  DOI：——

  日期：——