cephalosporin lactone | 851-59-2

• 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: cephalosporin lactone
• 英文别名: lactone of 7-phenylacetamidocephalosporanic acid；3-Hydroxymethyl-7-phenylacetylamino-ceph-3-en-4-saeure-lacton；3-Hydroxymethyl-7β-phenylacetamido-ceph-3-em-4ξ-carbonsaeure-lacton；N-((5aR)-1,7-dioxo-(5ar)-1,4,6,7-tetrahydro-3H,5aH-azeto[2,1-b]furo[3,4-d][1,3]thiazin-6t-yl)-2-phenyl-acetamide；7β-(2-phenyl-acetylamino)-cephalosporadesic acid lactone；(6R,7R)-3-Hydroxymethyl-7-(2-phenylacetamido)-3-cephem-4-carboxylic acid lactone；N-[(4R,5R)-3,11-dioxo-10-oxa-6-thia-2-azatricyclo[6.3.0.02,5]undec-1(8)-en-4-yl]-2-phenylacetamide
• CAS: 851-59-2
• 化学式: C₁₆H₁₄N₂O₄S
• 分子量: 330.364
• InChiKey: BQNGVFUMZXVPBG-IUODEOHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  cephalosporin lactone 在 水 作用下， 以 1,4-二氧六环 为溶剂， 生成 (R)-((R)-7-Oxo-1,2,5,7-tetrahydro-4H-furo[3,4-d][1,3]thiazin-2-yl)-phenylacetylamino-acetic acid
  参考文献：
  名称：

  Laws, Andrew P.; Layland, Nicola J.; Proctor, David G., Journal of the Chemical Society. Perkin transactions II, 1993, # 1, p. 17 - 21

  摘要：

  DOI：
• 作为产物：
  描述：

  头孢洛仑 在 盐酸 作用下， 以 丙酮 为溶剂， 生成 cephalosporin lactone
  参考文献：
  名称：

  922.头孢烷酸。第二部分 亲核试剂取代乙酰氧基

  摘要：

  DOI：

  10.1039/jr9650005015

文献信息

• Cephalosporanic acids. Part IV. 7-Acylamidoceph-2-em-4-carboxylic acids
  作者：J. D. Cocker、S. Eardley、G. I. Gregory、M. E. Hall、A. G. Long

  DOI：10.1039/j39660001142

  日期：——

  The combined action of bases and acid anhydrides on 7-acylamidocephalosporanic acids, and the action of bases on their esters, set up equilibria in which the corresponding Δ2-isomers predominate. The isomerisation represents a prototropic shift probably favoured by the sulphur atom in the dihydrothiazine ring. The acetoxy-group in the Δ2-compounds can be replaced by nucleophiles.

  的碱和酸酐7-acylamidocephalosporanic酸的联合作用，以及碱基对它们的酯的动作，设置了其中相应Δ均衡2 -异构体占优势。异构化表示质子交换，这可能是二氢噻嗪环中的硫原子所促进的。的乙酰氧基团在Δ 2 -化合物可以通过亲核试剂代替。
• New β-Lactam-Antibiotics. Fluorinated Cephalosporins. Preliminary Communication. Modifikationen von Antibiotika. 15. Mitteilung
  作者：Beat Müller、Heinrich Peter、Peter Schneider、Hans Bickel

  DOI：10.1002/hlca.19750580826

  日期：1975.11.5

  AbstractNeue Cephalosporine, die in 3‐Stellung eine Fluormethylgruppe aufweisen (9, 17/Schema 1), wurden ausgehend von 2b unter Verwendung von 2‐Chlor‐1,1,2‐trifluor‐triäthylamin als Fluorierungsmittel hergestellt. Mit Piperidin‐schwefeltrifluorid erhielt man ferner aus 18 die 3‐Difluormethyl‐cephemverbindung 19 (Schema 2), die nach bekannten Methoden in antibakteriell wirksame Cephalosporine (20a, b) übergeführt wurde. 3‐Fluor‐cephemderivate, z.B. 23b, liessen sich ausgehend von entsprechenden 3‐Hydroxy‐cephemverbindungen, mit diesem Reagens jedoch nur in sehr geringer Ausbeute herstellen.
• An Improved Process for the Preparation of Diphenylmethyl 7β-Phenylacetamido-3-hydroxymethyl-3-cephem-4-carboxylate
  作者：Keping Yu、Nan Sun、Shanzong Fang、Weimin Mo、Baoxiang Hu、Zhenlu Shen、Xinquan Hu

  DOI：10.1021/op900063e

  日期：2009.7.17

  An efficient and improved process for the preparation of diphenylmethyl 7 beta-phenylacetamido-3-hydroxymethyl-3-cephem-4-carboxylate was developed. With the commercially available 7-aminocephalosporanic acid (7-ACA) as starting material, up to 73.5% overall isolated yield of the tided compound was synthesized in two steps via direct phenylacetylation with phenylacetyl chloride, followed by basic hydrolysis and esterification with diphenyldiazomethane. The newly developed process obviated the use of protecting groups, reduced the environmental footprint, and could be easily controlled and conveniently scaled up for this pivotal intermediate in cephalosporin chemistry.
• Conversion of Penicillin to Cephalosporin Lactones. Preliminary Communication
  作者：Kapa K. Prasad、G�rard Schmid、Theodor Petrzilka

  DOI：10.1002/hlca.19760590649

  日期：——

  AbstractPenicillin G (1, R  CH2Ph) was converted to cephaloram‐ and 6‐epicephaloram lactones 11 and 12 respectively by the initial replacement of thiazolidine part of penicillin by the mercaptan 9 followed by intramolecular cyclization and subsequent introduction of double bond at C(3).
• TANAKA, HIDEO;TANIGUCHI, MASATOSHI;KAMEYAMA, YUTAKA;YAMAGUCHI, TAKEMA;SAS+, SYNLETT.,(1990) N1, C. 660-662
  作者：TANAKA, HIDEO、TANIGUCHI, MASATOSHI、KAMEYAMA, YUTAKA、YAMAGUCHI, TAKEMA、SAS+

  DOI：——

  日期：——