ethyl 8-amino-7-chloro-6-fluoro-4-oxo-1,2,3,4-tetrahydroquinoline-3-carboxylate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: ethyl 8-amino-7-chloro-6-fluoro-4-oxo-1,2,3,4-tetrahydroquinoline-3-carboxylate
• 英文别名: Ethyl 8-amino-7-chloro-6-fluoro-4-hydroxy-3-quinolinecarboxylate；ethyl 8-amino-7-chloro-6-fluoro-4-oxo-1H-quinoline-3-carboxylate
• 化学式: C₁₂H₁₀ClFN₂O₃
• 分子量: 284.674
• InChiKey: CMJPSOSYDDMTLF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  81.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl 8-amino-7-chloro-6-fluoro-4-oxo-1,2,3,4-tetrahydroquinoline-3-carboxylate 在 吡啶 、 calcium nitrite 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 33.0h， 生成 乙基7-氯-8-氰基-1-环丙基-6-氟-4-氧杂-1,4-二氢喹啉-3-羧酸酯
  参考文献：
  名称：

  一种普拉多沙星的制备方法

  摘要：

  本发明属于药物合成技术领域，具体为一种普拉多沙星的制备方法。本发明通过以4‑氟‑3‑氯‑2‑硝基苯胺为原料通过环化，还原等制备普拉多沙星(8‑氰基‑1‑环丙基‑6‑氟‑7‑(八氢化‑6H‑吡咯并[3，4‑b]吡啶‑6‑基)‑4‑氧代‑1,4‑二氢喹啉‑3‑羧酸)，该路线反应原材料廉价易得，合成路线简单，后处理易操作，仅需6步即可实现目标产物普拉多沙星，反应转率化高，反应过程简单易操作，所得产品纯度较高。

  公开号：

  CN108948011A
• 作为产物：
  描述：

  7-chloro-6-fluoro-4-hydroxy-8-nitroquinoline-3-carboxylic acid ethyl ester 在 锌 作用下， 以 苯甲醇 为溶剂， 反应 16.0h， 以95%的产率得到ethyl 8-amino-7-chloro-6-fluoro-4-oxo-1,2,3,4-tetrahydroquinoline-3-carboxylate
  参考文献：
  名称：

  一种普拉多沙星的制备方法

  摘要：

  本发明属于药物合成技术领域，具体为一种普拉多沙星的制备方法。本发明通过以4‑氟‑3‑氯‑2‑硝基苯胺为原料通过环化，还原等制备普拉多沙星(8‑氰基‑1‑环丙基‑6‑氟‑7‑(八氢化‑6H‑吡咯并[3，4‑b]吡啶‑6‑基)‑4‑氧代‑1,4‑二氢喹啉‑3‑羧酸)，该路线反应原材料廉价易得，合成路线简单，后处理易操作，仅需6步即可实现目标产物普拉多沙星，反应转率化高，反应过程简单易操作，所得产品纯度较高。

  公开号：

  CN108948011A

文献信息

• Process for the preparation of 4-hydroxy-quinoline-3-carboxylic acids
  申请人：Bayer Aktiengesellschaft

  公开号：US04804760A1

  公开（公告）日：1989-02-14

  A process for the preparation of a compound of the formula ##STR1## in which Y is a nitrile group, an ester group COOR.sup.1 or an acid amide CONR.sup.2 R.sup.3, R.sup.1, R.sup.2 and R.sup.3 each independently is hydrogen or C.sub.1 -C.sub.4 -alkyl, and R.sup.3 may also be phenyl, and X.sup.2, X.sup.3, X.sup.4 and X.sup.5 each independently is hydrogen, halogen, nitro, cyano, alkyl having 1-3 carbon atoms, alkoxy having 1-3 carbon atoms, alkylmercapto having 1-3 carbon atoms, alkyl-sulphonyl having 1-3 carbon atoms, or a phenylsulphonyl group which is optionally substituted in the aryl radical, comprising reacting an aminoacrylate of the formula in which X.sup.1 is halogen, a nitro group, an alkoxy, alkoxy, alkylmercapto or alkylsulphonyl group having 1-3 carbon atoms in each case, or an arylsulphonyl group, W is hydrogen or a --CH.sub.2 CH.sub.2 Z radical, Z is a nitrile group, an ester group COOR.sup.4 or an acid amide group CONR.sup.5 R.sup.6, and R.sup.4, R.sup.5 and R.sup.6 each independently is hydrogen or C.sub.1 -C.sub.4 -alkyl, and R.sup.5 may also be phenyl, with an acid acceptor in an aprotic solvent. Some of the reactants are new, as are the products which are intermediates for antibacterially active 1-alkyl-4-quinolone-3-carboxylic acids.

  一种制备公式##STR1##中化合物的过程，其中Y是腈基，酯基COOR.sup.1或酸酰胺CONR.sup.2R.sup.3，R.sup.1，R.sup.2和R.sup.3各自独立地是氢或C.sub.1-C.sub.4-烷基，而R.sup.3也可以是苯基，而X.sup.2，X.sup.3，X.sup.4和X.sup.5各自独立地是氢，卤素，硝基，氰基，具有1-3个碳原子的烷基，具有1-3个碳原子的烷氧基，具有1-3个碳原子的烷基硫醇基，具有1-3个碳原子的烷基磺酰基，或者是苯基磺酰基，该苯基磺酰基在芳基中可以选择性地被取代，包括在无极溶剂中用酸受体反应氨基丙酸酯的公式，其中X.sup.1是卤素，硝基，烷氧基，烷氧基，烷基硫醇基或烷基磺酰基，每种情况下都具有1-3个碳原子，或芳基磺酰基，W是氢或--CH.sub.2 CH.sub.2 Z基，Z是腈基，酯基COOR.sup.4或酸酰胺基CONR.sup.5R.sup.6，而R.sup.4，R.sup.5和R.sup.6各自独立地是氢或C.sub.1-C.sub.4-烷基，而R.sup.5也可以是苯基，反应物中有一些是新的，产品是抗菌活性1-烷基-4-喹啉酮-3-羧酸的中间体。
• 4-Hydroxy-quinoline-3-carboxylic
  申请人：Bayer Aktiengesellschaft

  公开号：US04870182A1

  公开（公告）日：1989-09-26

  A process for the preparation of a compound of the formula ##STR1## in which Y is a nitrile group, an ester group COOR.sup.1 or an acid amide CONR.sup.2 R.sup.3, R.sup.1, R.sup.2 and R.sup.3 each independently is hydrogen or C.sub.1 -C.sub.4 -alkyl, and R.sup.3 may also be phenyl, and X.sup.2, X.sup.3, X.sup.4 and X.sup.5 each independently is hydrogen, halogen, nitro, cyano, alkyl having 1-3 carbon atoms, alkoxy having 1-3 carbon atoms, alkylmercapto having 1-3 carbon atoms, alkylsulphonyl having 1-3 carbon atoms, or a phenylsulphonyl group which is optionally substituted in the aryl radical, comprising reacting an aminoacrylate of the formula in which X.sup.1 is halogen, a nitro group, an alkoxy, alkoxy, alkylmercapto or alkylsulphonyl group having 1-3 carbon atoms in each case, or an arylsulphonyl group, W is hydrogen or a --CH.sub.2 CH.sub.2 Z radical, Z is is a nitrile group, an ester group COOR.sup.4 or an acid amide group CONR.sup.5 R.sup.6, and R.sup.4, R.sup.5 and R.sup.6 each independently is hydrogen or C.sub.1 -C.sub.4 -alkyl, and R.sup.5 may also be phenyl, with an acid acceptor in an aprotic solvent. Some of the reactants are new, as are the products which are intermediates for antibacterially active 1-alkyl-4-quinolone-3-carboxylic acids.

  一种制备式为##STR1##化合物的方法，其中Y是腈基，酯基COOR.sup.1或酸酰胺CONR.sup.2R.sup.3，R.sup.1、R.sup.2和R.sup.3各自独立地是氢或C.sub.1-C.sub.4-烷基，且R.sup.3还可以是苯基，X.sup.2、X.sup.3、X.sup.4和X.sup.5各自独立地是氢、卤素、硝基、氰基、具有1-3个碳原子的烷基、具有1-3个碳原子的烷氧基、具有1-3个碳原子的烷基硫醇基、具有1-3个碳原子的烷基磺酰基或者是苯基磺酰基，其在芳基基团上可选择性地取代，包括在无极溶剂中与式为X.sup.1为卤素、硝基、烷氧基、烷氧基、具有1-3个碳原子的烷基硫醇基或烷基磺酰基的情况下，或者是芳基磺酰基，W是氢或--CH.sub.2 CH.sub.2 Z基团，Z是腈基、酯基COOR.sup.4或酸酰胺基团CONR.sup.5R.sup.6，R.sup.4、R.sup.5和R.sup.6各自独立地是氢或C.sub.1-C.sub.4-烷基，且R.sup.5还可以是苯基，与酸受体反应的方法。其中一些反应物是新的，产物是抗菌活性1-烷基-4-喹啉酮-3-羧酸的中间体。
• New quinolone compounds and preparation thereof
  申请人：STERLING DRUG INC.

  公开号：EP0090424A1

  公开（公告）日：1983-10-05

  Novel 1-R-1,4-dihydro-4-oxo-6-fluoro-7-(Z=N-)-quinolinecarboxylic acids and esters thereof, where R is amino, lower-alkylamino, 2-propenylamino or di-lower-alkylamino, R" is hydrogen or lower-alkyl, and Z=N is a heterocyclic group, useful as antibacterial agents, are prepared by reacting the corresponding 7-chloroquinoline derivatives with the appropriate heterocyclic compound, Z=NH. A preferred group of compounds are those where Z=N is 1-piperazinyl of 4-lower-alkyl-1-piperazinyl.

  新型 1-R-1,4-二氢-4-氧代-6-氟-7-(Z=N-)-喹啉羧酸及其酯类，其中 R 为氨基、低级烷基氨基、2-丙烯基氨基或二低级烷基氨基，R "为氢或低级烷基，Z=N 为杂环基团，可作为抗菌剂，通过相应的 7-氯喹啉衍生物与适当的杂环化合物 Z=NH 反应制备。 优选的一组化合物是 Z=N 为 1-哌嗪基或 4-低级烷基-1-哌嗪基的化合物。
• US4804760A
  申请人：——

  公开号：US4804760A

  公开（公告）日：1989-02-14
• US4870182A
  申请人：——

  公开号：US4870182A

  公开（公告）日：1989-09-26