diphenylmethyl 6β-(2-phenylacetamido)penicillanate 1-oxide | 51446-87-8

• 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: diphenylmethyl 6β-(2-phenylacetamido)penicillanate 1-oxide
• 英文别名: benzhydryl-6-phenylacetamidopenicillin β-sulfoxide；benzhydryl (2S,5R,6R)-3,3-dimethyl-4,7-dioxo-6-[(2-phenylacetyl)amino]-4lambda4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate；benzhydryl (2S,5R,6R)-3,3-dimethyl-4,7-dioxo-6-[(2-phenylacetyl)amino]-4λ4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
• CAS: 51446-87-8
• 化学式: C₂₉H₂₈N₂O₅S
• 分子量: 516.618
• InChiKey: DKEVWYKOXPQNPG-MVJCBFHXSA-N

物化性质

• 熔点：
  129 °C
• 沸点：
  789.2±60.0 °C(Predicted)
• 密度：
  1.38±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  37
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  112
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  diphenylmethyl 6β-(2-phenylacetamido)penicillanate 1-oxide 在 三氟乙酸 作用下， 以 various solvent(s) 为溶剂， 反应 1.0h， 以91%的产率得到咪唑并[1,2-a]吡啶-2-甲醛,8-氯-
  参考文献：
  名称：

  Deprotection of carboxylic esters of .beta.-lactam homologs. Cleavage of p-methoxybenzyl, diphenylmethyl, and tert-butyl esters effected by a phenolic matrix

  摘要：

  p-Methoxybenzyl, diphenylmethyl, and tert-butyl esters were deprotected by gentle heating in phenol. This method of ester cleavage played an important role in beta-lactam synthesis. The mechanism of the reaction is believed to involve a proton relay through a hydrogen-bonded phenolic matrix.

  DOI：

  10.1021/jo00011a034
• 作为产物：
  描述：

  diphenylmethyl 6β-(2-phenylacetamido)penicillanate 在 oxone||potassium monopersulfate triple salt 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 7.0h， 以95.7%的产率得到diphenylmethyl 6β-(2-phenylacetamido)penicillanate 1-oxide
  参考文献：
  名称：

  一种青霉素G亚砜二苯甲酯的合成方法

  摘要：

  本发明公开了一种青霉素G亚砜二苯甲酯的合成方法。以青霉素G钾盐为起始原料，先酯化，再经2KHSO5·KHSO4·K2SO4氧化合成青霉素G亚砜二苯甲酯，产品纯度99％以上，总摩尔收率95％以上，适用于工业化生产。本发明具有原料易得，收率高，污染少，安全系数高，易于操作等优点。

  公开号：

  CN110845516B

文献信息

• Scott, A. Ian; Shankaranarayan, Ramaswamy; Chung, Sung-Kee, Heterocycles, 1990, vol. 30, # 2, p. 909 - 927
  作者：Scott, A. Ian、Shankaranarayan, Ramaswamy、Chung, Sung-Kee

  DOI：——

  日期：——
• 2,4,6-Tripyridino-1,3,5-triazine Trichloride, a New and Mild Esterification Agent for Preparation of Penicillin Esters
  作者：Masayuki Murakami、Makoto Hajima、Fumitaka Takami、Mitsuru Yoshioka

  DOI：10.3987/com-90-5565

  日期：——

  Cyanuric chloride reacted with 3 molar equivalents of pyridine to give 2,4,6-tripyridinio-1,3,5-triazine trichloride, which was found to condense penicillins with alcohols under mild conditions to afford penicillin esters in good yields. Application to preparation of cephalosporin esters also is discussed.
• A Novel Approach to Cephalosporins From Allenylazetidinones: A New Cyclization Strategy via Tandem Cuprate Addition-Sulfenylation
  作者：Joydeep Kant、Jeanine A. Roth、Carl E. Fuller、Donald G. Walker、Daniel A. Benigni、Vittorio Farina

  DOI：10.1021/jo00096a045

  日期：1994.8

  An efficient approach to the synthesis of 3-substituted cephems bearing carbon-based substituents of choice at the C(3) position from inexpensive penicillins is described. The strategy involves the synthesis of an allenylazetidinone from penicillin sulfoxide followed by the addition of an organocuprate at low temperature. Organocuprates undergo 1,4-conjugate addition at the central allenic carbon of the allenylazetidinone to form a carbon-carbon bond which is followed by ring closure via an intramolecular sulfenylation reaction. The chemistry has been applied to the synthesis of a variety of 3-substituted cephems bearing substituents such as alkyl, cycloalkyl, aryl, alkenyl, and allyl. Precursors to the synthesis of important antibiotics, i.e., Cefadroxil, Cefixime, and Cefzil, are also available from this novel approach. The methodology is not limited to carbon-based 3-substituted cephems, but provides access to some 3-norcephalosporins as well.
• TANAKA, MAMORU;KONOIKE, TOSHIRO;YOSHIOKA, MITSURU, SYNTHESIS,(1989) N, C. 197-198
  作者：TANAKA, MAMORU、KONOIKE, TOSHIRO、YOSHIOKA, MITSURU

  DOI：——

  日期：——
• TORII, SIGERU;TANAKA, HIDEO;TANIGUCHI, MASATOSHI;KAMEYAMA, YUTAKA;SASAOKA+, J. ORG. CHEM., 56,(1991) N1, C. 3633-3637
  作者：TORII, SIGERU、TANAKA, HIDEO、TANIGUCHI, MASATOSHI、KAMEYAMA, YUTAKA、SASAOKA+

  DOI：——

  日期：——