2,2,2-trichloroethyl 6β-phenylacetamidopenicillanate | 26774-86-7

• 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: 2,2,2-trichloroethyl 6β-phenylacetamidopenicillanate
• 英文别名: 6β-(2-phenyl-acetylamino)-penicillanic acid 2,2,2-trichloro-ethyl ester；6β-phenylacetamidopenicillanic acid 2,2,2-trichloroethyl ester；2',2',2'-trichloroethyl 6-phenylacetamido penicillanate；2,2,2-trichloroethyl (2S,5R,6R)-3,3-dimethyl-7-oxo-6-[(phenylacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate；2,2,2-trichloroethyl (2S,5R,6R)-3,3-dimethyl-7-oxo-6-[(2-phenylacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
• CAS: 26774-86-7
• 化学式: C₁₈H₁₉Cl₃N₂O₄S
• 分子量: 465.785
• InChiKey: HTXDYUAMCONEPD-VNHYZAJKSA-N

物化性质

• 熔点：
  157-159 °C (decomp)
• 沸点：
  701.9±60.0 °C(Predicted)
• 密度：
  1.49±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  2,2,2-trichloroethyl 6β-phenylacetamidopenicillanate 在 三氟化硼乙醚 、 sodium acetate 、 dinitrogen tetraoxide 作用下， 以 二氯甲烷 为溶剂， 反应 4.5h， 生成 2,2,2-trichloroethyl 6α-(hydroxybutyloxy)penicillanate
  参考文献：
  名称：

  Giddings, Peter J.; John, D. Ivor; Thomas, Eric J., Journal of the Chemical Society. Perkin transactions I, 1982, # 11, p. 2757 - 2766

  摘要：

  DOI：

文献信息

• Conversion of acylamidopenicillins to phosphoramidopenicillins, and removal of their phosphoryl side chain.
  作者：MASATAKA FUKUMURA、NORITAKA HAMMA、TAKENARI NAKAGOME

  DOI：10.1248/cpb.24.3058

  日期：——

  On sequential treatment of benzylpenicillanates (1) or their sulfoxides (7) with phosphorus pentachloride, methanol, and sodium bicarbonate or dimethylaniline, 6-(dimethylphosphoramido) penicillins (5) or their sulfoxides (8) were obtained. 6-(Dimethylphosphoramido) penicillin sulfoxides (8) were rearranged thermally to their corresponding desacetoxycephalosporins (10). The dimethylphosphoryl group of 7-(dimethylphosphoramido) desacetoxycephalosporins (10) was removed by either a 85% phosphoric acid or polyphosphoric acid, which caused the degradation of β-lactam ring in 6-(dimethylphosphoramido) penicillins (5) and their sulfoxides (8). The dimethylphosphoryl group of penicillins and desacetoxycephalosporins was also removed by phosgene and pyridine to give 6-isocyanatopenicillins (16) and 7-isocyanatodesacetoxycephalosporins (15), respectively.

  用五氯化磷、甲醇、碳酸氢钠或二甲基苯胺依次处理苄基青霉烷酸酯（1）或其硫醚（7），可得到 6-（二甲基磷酰氨基）青霉素（5）或其硫醚（8）。6-（二甲基磷酰氨基）青霉素硫醚（8）经热重排后生成相应的去乙酰氧基头孢菌素（10）。用 85% 的磷酸或多磷酸去除 7-（二甲基磷酰氨基）去乙酰氧基头孢菌素（10）的二甲基磷酰基，可使 6-（二甲基磷酰氨基）青霉素（5）及其硫醚（8）中的 β-内酰胺环降解。青霉素和去乙酰氧基头孢菌素的二甲基磷酰也可通过光气和吡啶去除，分别得到 6-异氰酸青霉素（16）和 7-异氰酸去乙酰氧基头孢菌素（15）。
• Process for chemically removing the acyl sidechain from cephalosporins
  申请人：E. R. Squibb & Sons, Inc.

  公开号：US04252973A1

  公开（公告）日：1981-02-24

  A process for removing the acyl sidechain from penicillins and cephalosporins which comprises chlorinating the acyl compound and treating the resulting iminochloride with an o-aminothiophenol to obtain the corresponding 6.beta.-aminopenicillin or 7.beta.-aminocephalosporin.

  一种从青霉素和头孢菌素中去除酰基侧链的方法，包括氯化酰基化合物并用o-氨基硫酚处理所得的亚胺氯化物，以获得相应的6-β-氨基青霉素或7-β-氨基头孢菌素。
• Penicillin derivatives, process for their preparation and pharmaceutical compositions containing certain of these compounds
  申请人：BEECHAM GROUP PLC

  公开号：EP0013617A1

  公开（公告）日：1980-07-23

  This invention relates to a process for the preparation of certain penicillin derivatives which are useful as β-lactamase inhibitors. The compounds which may be prepared by the process of this invention have formula (I), or a pharmaceutically acceptable salt or ester thereof: wherein R represents hydrogen, halogen, C1-6alkylthio, C1-6alkyl or alkyl substituted with phenyl, carboxy, C1-6alkoxycarbonyl, hydroxyorC1-6alkylthio, and n is zero, 1 or 2. In addition certain of the compounds produced by the process of the invention are novel compounds.

  本发明涉及一种制备某些青霉素衍生物的工艺，这些衍生物可用作β-内酰胺酶抑制剂。可通过本发明工艺制备的化合物具有式（I）或其药学上可接受的盐或酯： 其中R代表氢、卤素、C1-6烷硫基、C1-6烷基或被苯基、羧基、C1-6烷氧基羰基、羟基或C1-6烷硫基取代的烷基，n为0、1或2。此外，本发明工艺生产的某些化合物是新型化合物。
• Processes for preparation of beta-lactam compounds
  申请人：ELI LILLY AND COMPANY

  公开号：EP0014567A1

  公开（公告）日：1980-08-20

  Kinetically controlled triaryl phosphite halogen compounds of the formula wherein X is Cl or Br, and Z is hydrogen, halo, C1-C4 alkyl or C1-C4 alkoxy, are used to effect a) halogenation of a C-6 or C-7 acylamine penicillin or cephalosporin, b) halogenation of a 3-hydroxy-3-cephem, c) one step halogenation of a C-7 acylamine-3-hydroxy- cephem d) reduction of a cephalosporin sulfoxide e) one step reduction/halogenation of a 3-hydroxy cephalosporin sulfoxide f) one step reduction/halogenation of a C-7 acylamine cephalosporin sulfoxide g) one step reduction/halogenation of a C-7 acylamino-3-hydroxy cephalosporin sulfoxide.

  动力学控制的三芳基亚磷酸酯卤素化合物的化学式为 其中 X 是 Cl 或 Br，Z 是氢、卤素、C1-C4 烷基或 C1-C4 烷氧基，用于实现 a) C-6 或 C-7 氨基酰青霉素或头孢菌素的卤化、 b) 卤化 3-羟基-3-头孢菌素、 c) C-7 乙酰氨基-3-羟基-头孢的一步卤化反应 d) 还原头孢菌素亚砜 e) 一步还原/卤化 3-羟基头孢菌素亚砜 f) C-7 乙酰氨基头孢菌素亚砜的一步还原/卤化反应 g) C-7 乙酰氨基-3-羟基头孢菌素亚砜的一步还原/卤化反应。
• Process for chemically removing the acyl sidechain from cephalosporins and penicillins
  申请人：E.R. Squibb & Sons, Inc.

  公开号：EP0022326A1

  公开（公告）日：1981-01-14

  A process is provided for removing the acyl sidechain from penicillins and cephalosporins which comprises chlorinating the acyl compound and treating the resulting iminochloride with an o-aminothiophenol to obtain the corresponding 6β-aminopenicillin or 7β-aminocephalosporin.

  提供了一种从青霉素和头孢菌素中去除酰基侧链的工艺，该工艺包括氯化酰基化合物，并用邻氨基苯硫酚处理生成的亚氨基盐酸盐，以获得相应的 6β-aminopenicillin 或 7β-aminocephalosporin。