(6R)-3-formyl-8-oxo-7t-(2-phenyl-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-3-ene-2c-carboxylic acid | 39914-30-2

• 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: (6R)-3-formyl-8-oxo-7t-(2-phenyl-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-3-ene-2c-carboxylic acid
• 英文别名: 3-Formyl-7beta-phenylacetylamino-ceph-2-em-4alpha-carboxylic acid；(2R,6R,7R)-3-formyl-8-oxo-7-[(2-phenylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-3-ene-2-carboxylic acid
• CAS: 39914-30-2
• 化学式: C₁₆H₁₄N₂O₅S
• 分子量: 346.364
• InChiKey: HTIQAPLGXYFRMO-UMVBOHGHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  129
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (6R)-3-formyl-8-oxo-7t-(2-phenyl-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-3-ene-2c-carboxylic acid 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 生成 (6R)-5t,8-dioxo-7t-(2-phenyl-acetylamino)-(6rH)-5λ4-thia-1-aza-bicyclo[4.2.0]oct-2-ene-3-carboxylic acid 2-bromo-ethyl ester
  参考文献：
  名称：

  Neue β-Lactam-Antibiotika. Cephem-Derivate mit elektronenanziehenden Substituenten in 3-Stellung. Modifikationen von Antibiotika. 14. Mitteilung

  摘要：

  New β‐lactam antibiotics. Cephem derivatives with electron withdrawing substituents at position 3Oxidation of the 3‐formyl‐2‐cephem compound 1 according to Corey [6] gave 2‐cephem‐3‐carboxylic esters 4a, b, c (Scheme 1), which proved to be useful intermediates for the synthesis of cephalosporins bearing in position 3 a methoxycarbonyl group (10a, b, c, d / Scheme 2) or a carboxy group (20, 25, 30/Schemes 3, 4). The 3‐formyl‐3‐cephem compounds 31a, b could be transformed into cyano‐ (33a) or methoxyiminomethyl‐ (36a, c, d) cephems (Scheme 5), which represent further examples of cephalosporins with electron withdrawing groups in position 3.

  DOI：

  10.1002/hlca.19750580825
• 作为产物：
  描述：

  (6R)-3-hydroxymethyl-8-oxo-7t-(2-phenyl-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-3-ene-2c-carboxylic acid 在 chromium(VI) oxide 、 硫酸 作用下， 以 丙酮 为溶剂， 生成 (6R)-3-formyl-8-oxo-7t-(2-phenyl-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-3-ene-2c-carboxylic acid
  参考文献：
  名称：

  Neue ?-Lactam-Antibiotika. �ber die Darstellung und Decarbonylierung von 3-Formylcephem-Verbindungen. Modifikationen von Antibiotica, 12. Mitteilung [1]

  摘要：

  AbstractBenzhydrylic esters of 3‐unsubstituted cephem‐4‐carboxylic acids of types 9 and 10 (Scheme 2) are prepared by decarbonylation of esters of 3‐formylcephem compounds of type 2 with tris‐triphenylphosphine‐rhodium chloride. The preparation of the starting materials 2 and 5, as well as of the nucleus 13 is described.

  DOI：

  10.1002/hlca.19740570715

文献信息

• Cephalosporin compounds
  申请人：Ciba-Geigy Corporation

  公开号：US04458069A1

  公开（公告）日：1984-07-03

  The invention concerns the decarbonylation of the formyl group in 7-amino-3-formyl-ceph-2-em-4-carboxylic acid compounds and 7-amino-3-formyl-ceph-3-em-4-carboxylic acid compounds by treatment with a platinum metal complex capable of taking up carbon monoxide. Also included are the 7-amino-ceph-2-em-4-carboxylic acid compounds and the 1-oxides of 7-amino-ceph-3-em-4-carboxylic acid compounds; these compounds are used as intermediates.

  本发明涉及使用能够吸收一氧化碳的铂金属配合物处理7-氨基-3-甲酰基-头孢-2-乙烯-4-羧酸化合物和7-氨基-3-甲酰基-头孢-3-乙烯-4-羧酸化合物中的甲酰基基团的脱羰基化。还包括7-氨基-头孢-2-乙烯-4-羧酸化合物和7-氨基-头孢-3-乙烯-4-羧酸化合物的1-氧化物；这些化合物用作中间体。
• Process for the manufacture of 8-oxo-5-thia-1-azabicyclo
  申请人：Ciba-Geigy Corporation

  公开号：US04269977A1

  公开（公告）日：1981-05-26

  The invention concerns the decarbonylation of the formyl group in 7-amino-3-formyl-ceph-2-em-4-carboxylic acid compounds and 7-amino-3-formyl-ceph-3-em-4-carboxylic acid compounds by treatment with a platinum metal complex capable of taking up carbon monoxide. Also included are the 7-amino-ceph-2-em-4-carboxylic acid compounds and the 1-oxides of 7-amino-ceph-3-em-4-carboxylic acid compounds; these compounds are used as intermediates.

  本发明涉及使用能够吸收一氧化碳的铂金属配合物处理7-氨基-3-甲酰基-头孢-2-乙烯-4-羧酸化合物和7-氨基-3-甲酰基-头孢-3-乙烯-4-羧酸化合物中的甲酰基基团的脱羰基化。还包括7-氨基-头孢-2-乙烯-4-羧酸化合物和7-氨基-头孢-3-乙烯-4-羧酸化合物的1-氧化物；这些化合物被用作中间体。
• US4269977A
  申请人：——

  公开号：US4269977A

  公开（公告）日：1981-05-26
• US4458069A
  申请人：——

  公开号：US4458069A

  公开（公告）日：1984-07-03
• Neue β-Lactam-Antibiotika. Cephem-Derivate mit elektronenanziehenden Substituenten in 3-Stellung. Modifikationen von Antibiotika. 14. Mitteilung
  作者：Heinrich Peter、Beat Müller、Hans Bickel

  DOI：10.1002/hlca.19750580825

  日期：1975.11.5

  New β‐lactam antibiotics. Cephem derivatives with electron withdrawing substituents at position 3Oxidation of the 3‐formyl‐2‐cephem compound 1 according to Corey [6] gave 2‐cephem‐3‐carboxylic esters 4a, b, c (Scheme 1), which proved to be useful intermediates for the synthesis of cephalosporins bearing in position 3 a methoxycarbonyl group (10a, b, c, d / Scheme 2) or a carboxy group (20, 25, 30/Schemes 3, 4). The 3‐formyl‐3‐cephem compounds 31a, b could be transformed into cyano‐ (33a) or methoxyiminomethyl‐ (36a, c, d) cephems (Scheme 5), which represent further examples of cephalosporins with electron withdrawing groups in position 3.