(R)-3-chloromethyl-2-((1R)-7-oxo-3-phenoxymethyl-(1rH,5cH)-4-thia-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl)-but-3-enoic acid benzyl ester | 70379-78-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: (R)-3-chloromethyl-2-((1R)-7-oxo-3-phenoxymethyl-(1rH,5cH)-4-thia-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl)-but-3-enoic acid benzyl ester
• 英文别名: benzyl (2R)-3-(chloromethyl)-2-[(1R,5R)-7-oxo-3-(phenoxymethyl)-4-thia-2,6-diazabicyclo[3.2.0]hept-2-en-6-yl]but-3-enoate
• CAS: 70379-78-1
• 化学式: C₂₃H₂₁ClN₂O₄S
• 分子量: 456.95
• InChiKey: NUNZIOTUZQWQOI-KCZVDYSFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.65
• 重原子数：
  31.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  68.2
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (R)-3-chloromethyl-2-((1R)-7-oxo-3-phenoxymethyl-(1rH,5cH)-4-thia-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl)-but-3-enoic acid benzyl ester 在 氨 作用下， 以 1,4-二氧六环 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 (6R,7R)-8-Oxo-3-pentachlorophenylsulfanylmethyl-7-(2-phenoxy-acetylamino)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzyl ester
  参考文献：
  名称：

  Penicillin-cephalosporin conversion IV. Direct synthesis of 3'-thiosubstituted cephalosporins from thiazoline-azetidinones

  摘要：

  DOI：

  10.1016/s0040-4039(00)87378-5
• 作为产物：
  描述：

  10-chloro-1α-oxo-6β-(2-phenyl-acetylamino)-1λ4-penicillanic acid benzyl ester 在 亚磷酸三乙酯 作用下， 生成 (R)-3-chloromethyl-2-((1R)-7-oxo-3-phenoxymethyl-(1rH,5cH)-4-thia-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl)-but-3-enoic acid benzyl ester
  参考文献：
  名称：

  Uyeo,S. et al., Heterocycles, 1978, vol. 10, p. 99 - 104

  摘要：

  DOI：

文献信息

• Penicillin-Cephalosporin Conversion. VII. An Improved Synthesis of 3-Methylenecephams
  作者：Shigeru Torii、Hideo Tanaka、Takashi Siroi、Tomoyuki Madono、Norio Saitoh、Michio Sasaoka、Junzo Nokami

  DOI：10.1246/bcsj.56.1567

  日期：1983.5

  Efficient conversion of 2-(7-oxo-2,6-diaza-4-thiabicyclo[3.2.0]hept-2-en-6-yl)-3-chloromethyl-3-butenoates (4), derived from natural penicillins, into 3-methylenecephams (1) has been performed by a simple two-step operation, which comprises replacement of the allylic chlorine atom of 4 with iodine and subsequent acid-catalyzed hydrolysis, leading to 1 in 70–54% overall yields. In the latter step, the ring opening of the thiazoline moiety and the intramolecular substitution of the iodide with the thiol group proceed simultaneously.

  从天然青霉素中提取的 2-(7-氧代-2,6-二氮杂-4-硫杂双环[3.2.0]庚-2-烯-6-基)-3-氯甲基-3-丁烯酸盐 (4) 通过简单的两步操作被高效地转化成了 3-亚甲基樟脑 (1)，其中包括用碘取代 4 的烯丙基氯原子以及随后的酸催化水解，从而得到了总收率为 70-54% 的 1。在后一个步骤中，噻唑啉分子的开环和碘化物与硫醇基团的分子内取代同时进行。
• Prominent Aspects of Electroorganic Synthesis in β-Lactam Chemistry
  作者：Sigeru Torii、Hideo Tanaka、Michio Sasaoka、Norio Saitoh、Takashi Siroi、Junzo Nokami

  DOI：10.1002/bscb.19820911202

  日期：——

  AbstractThe potentiality of electrolysis procedures in the penicillin‐cephalosporin conversion as well as in the direct transform of penicillins into oxazolineazetidinones as an intermediate for the preparation of the sulfur‐free analogues of cephalosporins are discussed. Especially, a chemoselective electrolytic chlorination of methyl group of 3‐methyl‐3‐butenoate moiety of thiazolineazetidinone derived from penicillins, a direct synthesis of 3′‐thiosubstituted cephalosporins from the thiazoline‐azetidinones, an improved synthesis of exomethylenecephams, an efficient route to 3‐chloromethyl‐Δ3‐cephems, electrochemical S‐S bond fission of 4‐(2‐benzothiazolyldithio) azetidinones, a direct transformation of penicillins into oxazoline‐azetidinones by chloride salt‐promoted electrolysis, and a versatile intermediate for new β‐lactam antibiotics are presented.
• SIROI, KEHJSI;SAJTO, NORIO;SASAOKA, MITIO;TORII, SIGEHSI;TANAKA, XIDEHO;N+
  作者：SIROI, KEHJSI、SAJTO, NORIO、SASAOKA, MITIO、TORII, SIGEHSI、TANAKA, XIDEHO、N+

  DOI：——

  日期：——