2-chloro-3,4-diacetoxybenzoic acid | 108098-48-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-chloro-3,4-diacetoxybenzoic acid
• 英文别名: 3,4-diacetyloxy-2-chlorobenzoic acid
• CAS: 108098-48-2
• 化学式: C₁₁H₉ClO₆
• 分子量: 272.642
• InChiKey: FWIZEEJMAMRYAR-UHFFFAOYSA-N

物化性质

• 沸点：
  428.2±45.0 °C(Predicted)
• 密度：
  1.441±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  89.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-chloro-3,4-diacetoxybenzoic acid 在 氯化亚砜 作用下， 反应 0.33h， 以100%的产率得到2-chloro-3,4-diacetoxybenzoyl chloride
  参考文献：
  名称：

  Pharmacokinetics of catechol cephalosporins. The effect of incorporating substituents into the catechol moiety on pharmacokinetics in a marmoset model

  摘要：

  Two series of cephalosporins A and B have been synthesized, bearing at C-3' catechols substituted with various electron withdrawing groups (Y) and differing links (X), and were evaluated for their in vitro antibacterial activity and their pharmacokinetics in marmosets. Compounds in series A, bearing an isobutyric oxime substituent, proved to be highly active against Gram-negative organisms and were especially noteworthy for showing long elimination phase (beta) half-lives in marmosets. It was established that introduction of electron withdrawing substituents greatly increased the beta-half-lives of compounds (5, X = NHCO, Y = H, t1/2 = 1.25 h, AUC = 27 mg/h per L; 11, X = NHCO, Y = 5-Cl, t1/2, = 4.5 h, AUC = 638 mg/h per L) and that the nature of the link also influenced t1/2, the highest values being obtained when X = NHCO and OCO. Acidities (pK(a) values) of the substituted catechols were measured, and relationships between the acidities and half-lives were evaluated. Thus it was established that the more acidic catechols gave the longest half-lives (12, X = NHCO, Y = 2,5-Cl2, t1/2 = 8.2 h, AUC = 461 mg/h per L). Further elaboration of the catechol to bicyclic systems maintained good pharmacokinetics when the pK(a) was sufficiently acidic.

  DOI：

  10.1021/jm00092a015
• 作为产物：
  描述：

  2-氯-3,4-羟基苯甲酸 在 硫酸 ice 、 水 作用下， 以 乙酸酐 、 ice water 为溶剂， 反应 1.5h， 以to give 2-chloro-3,4-diacetoxybenzoic acid (16.68 g)的产率得到2-chloro-3,4-diacetoxybenzoic acid
  参考文献：
  名称：

  Piperaziniocephalosporins

  摘要：

  化学式为：##STR1##的抗菌羟基芳基哌嗪头孢菌素，其中R.sup.1是氨基或酰胺基；R.sup.2是H或甲氧基；R.sup.3是烷基；R.sup.4是--(P-C-Q).sub.n --，其中P和Q分别是H，烷基或OH，或P和Q组合形成氧化物，n为0或4；R.sup.5是取代或未取代的羟基芳基；R.sup.6带有负电荷，是COO，或与可选的保护羧基结合形成阴离子；X是O，S或S.fwdarw.O；包含其的抗菌制剂；使用其杀菌和预防或治疗细菌感染的方法；以及头孢菌素的合成方法。

  公开号：

  US05143910A1

文献信息

• US5143910A
  申请人：——

  公开号：US5143910A

  公开（公告）日：1992-09-01