(6R,7R)-7-phenylacetamido-3-[(Z)-propen-1-yl]-3-cephem-4-carboxylic acid p-methoxybenzyl ester | 120635-31-6

• 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: (6R,7R)-7-phenylacetamido-3-[(Z)-propen-1-yl]-3-cephem-4-carboxylic acid p-methoxybenzyl ester
• 英文别名: (7R,8R)-7-phenylacetamido-3-[(Z)-propen-1-yl]-3-cephem-4-carboxylic acid p-methoxybenzyl ester；7-phenylacetamido-3-[(Z)-propen-1-yl]-3-cephem-4-carboxylic acid p-methoxybenzyl ester；(4-methoxyphenyl)methyl (6R,7R)-8-oxo-7-[(2-phenylacetyl)amino]-3-[(Z)-prop-1-enyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
• CAS: 120635-31-6
• 化学式: C₂₆H₂₆N₂O₅S
• 分子量: 478.569
• InChiKey: WAMZYJMUNSCWJN-RVMAHYDGSA-N

物化性质

• 沸点：
  759.3±60.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  34
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  110
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (7R)-7-[(phenylacetyl)amino]-3-trifluoromethanesulfonyloxy-3-cephem-4-carboxylate, 4-methoxybenzyl ester 、 (Z)-1-propenyltributyltin 在 tris-(dibenzylideneacetone)dipalladium(0) 作用下， 以 二氯甲烷 为溶剂， 反应 0.05h， 以82%的产率得到(6R,7R)-7-phenylacetamido-3-[(Z)-propen-1-yl]-3-cephem-4-carboxylic acid p-methoxybenzyl ester
  参考文献：
  名称：

  Baker, Stephen R.; Roth, Gregory P.; Sapino, Chester, Synthetic Communications, 1990, vol. 20, # 14, p. 2185 - 2189

  摘要：

  DOI：

文献信息

• [EN] PROCESSES FOR THE PREPARATION OF CEPHALOSPORIN DERIVATIVES<br/>[FR] PROCEDES DE PREPARATION DE DERIVES DE CEPHALOSPORINE
  申请人：CJ CORP

  公开号：WO2005042544A1

  公开（公告）日：2005-05-12

  Provided is a process for preparing a compound of formula 1 or its salt. The process includes reacting a compound of formula 4 with acetaldehyde in a mixed solvent including water, isopropanol, and methylenechloride in a volume ratio of 1:3-6:11-14 in the presence of a first base to stereospecifically prepare a compound of formula 3 and reacting the compound of the formula 3 with an anhydrous compound of formula 2 in the presence of a second base.

  提供了一种制备化合物1或其盐的方法。该方法包括在水、异丙醇和二氯甲烷的混合溶剂中，以1:3-6:11-14的体积比例，将化合物4与乙醛在第一碱的存在下反应，立体特异性地制备化合物3，并将化合物3与无水化合物2在第二碱的存在下反应。
• [EN] PROCESSES FOR THE PREPARATION OF CEPHEM DERIVATIVES<br/>[FR] PROCEDES DE PREPARATION DE DERIVES DE CEPHEME
  申请人：CJ CORP

  公开号：WO2005042543A1

  公开（公告）日：2005-05-12

  Provided is a process for preparing a compound of formula 1 or its salt, which includes reacting a compound of formula 2 with a compound of formula 3 in the presence of a base.

  提供了一种制备化合物1或其盐的过程，包括在碱的存在下将化合物2与化合物3反应。
• A facile synthesis of C(3)-alkenyl substituted cephems through addition-cyclization of allenecarboxylates derived from penicillin
  作者：Hideo Tanaka、Yutaka Kameyama、Shin-ichi Sumida、Sigeru Torii

  DOI：10.1016/s0040-4039(00)60924-3

  日期：1992.11

  A short-cut route to cephalosporins bearing alkenyl substituents on the C(3)-position through copper(I) chloride-promoted Michael-type addition of alkenyltributyltins to allenecarboxylates, derived from penicillin, is described.

  描述了一条通向头孢菌素的捷径，该头孢菌素通过氯化铜（I）促进烯基三丁基锡与烯丙基羧酸酯的迈克尔型加成反应而衍生自青霉素，而头孢菌素在C（3）-位上带有烯基取代基。
• Cephem compound, its production and its use for producing cephem antibiotics
  申请人：SUMITOMO CHEMICAL COMPANY, LIMITED

  公开号：EP0634415A2

  公开（公告）日：1995-01-18

  A 3-[(E)-1-propenyl]cephem derivative represented by formula (I) : wherein R represents hydrogen, an amino protecting group or a group of formula (II) : in which R3 is an amino protecting group, R4 is a hydroxy protecting group, and W is -CH= or -N=, R2 represent a carboxy protecting group and X represents hydrogen or chlorine ; or a salt thereof ; may be prepared by isomerizing the corresponding 3-[(Z)-1-propenyl]cephem compound in an inert organic solvent in the presence of an aromatic thiol. These compounds are useful as intermediates for cephem antibiotics. A compound of formula (I) wherein X is chlorine can be converted into a 3-[(E)-3- ammonio-1-propenyl]cephem derivative by reaction with a tertiary amine.

  式 (I) 所代表的 3-[(E)-1-丙烯基]头孢烷衍生物： 其中 R 代表氢、氨基保护基团或式（II）的基团： 其中 R3 是氨基保护基团，R4 是羟基保护基团，W 是-CH= 或-N=，R2 代表羧基保护基团，X 代表氢或氯。这些化合物可作为头孢抗生素的中间体。其中 X 为氯的式 (I) 化合物可通过与叔胺反应转化为 3-[(E)-3-氨-1-丙烯基]cephem 衍生物。
• Palladium catalysis in cephalosporin chemistry: general methodology for the synthesis of cephem side chains
  作者：Vittorio Farina、Stephen R. Baker、Daniel A. Benigni、Sheila I. Hauck、Chester Sapino

  DOI：10.1021/jo00310a014

  日期：1990.11