6,6-dibromo-3α-hydroxymethyl-2,2-dimethylpenam | 116114-76-2

• 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: 6,6-dibromo-3α-hydroxymethyl-2,2-dimethylpenam
• CAS: 116114-76-2
• 化学式: C₈H₁₁Br₂NO₂S
• 分子量: 345.055
• InChiKey: DXMSEYXCFOUKAS-UJURSFKZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.53
• 重原子数：
  14.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  40.54
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  6,6-dibromo-3α-hydroxymethyl-2,2-dimethylpenam 在 吡啶 、 potassium permanganate 作用下， 以 水 、 溶剂黄146 、 乙腈 为溶剂， 反应 2.17h， 生成 Phosphoric acid (2S,5R)-6,6-dibromo-3,3-dimethyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]hept-2-ylmethyl ester diphenyl ester
  参考文献：
  名称：

  Synthesis and human leukocyte elastase inhibitory evaluation of phosphate triesters and acyl phosphates of penam sulfides and sulfones

  摘要：

  The synthesis of 6,6-dibromo-3 alpha-(diphenylphosphate)oxymethyl-2,2-dimethyl penam sulfone (3a), 6 alpha -chloro-3 alpha-(diphenylphosphate)oxymethyl-2,2-dimethyl penam sulfone (3b), benzyl 6 alpha-(diphenyl-phosphate)oxypenicillanate sulfone (4) and 6,6-dibromo-3 alpha-(methylphosphate)carbonyl-2,2-dimethylpenam sulfone (12) are reported. When tested as inhibitors of human leukocyte elastase, the compound 4 proved to be the most active. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00139-0
• 作为产物：
  描述：

  6,6-二溴青霉烷酸 在 dimethyl sulfide borane 作用下， 以 四氢呋喃 为溶剂， 生成 6,6-dibromo-3α-hydroxymethyl-2,2-dimethylpenam
  参考文献：
  名称：

  Solid-phase based synthesis of biologically promising triazolyl aminoacyl (peptidyl) penicillins

  摘要：

  An efficient and versatile methodology for the preparation of valuable triazolyl aminoacyl (peptidyl) penicillins is described. Solid-phase Cu(I)-catalyzed Huisgen 1,3-dipolar cycloaddition was used as the key step showing general applicability and excellent regioselectivity either with CuI or [Cu(CH3CN)(4)]PF6 as Cu(I) source. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.11.113

文献信息

• Selective oxidation of penicillin derivatives to penicillin (1R) and (1S)-sulfoxides using dimethyldioxirane
  作者：Gerardo O. Danelon、Ernesto G. Mata、Oreste A. Mascaretti

  DOI：10.1016/s0040-4039(00)61499-5

  日期：1993.12

  6-dihalo-, 6β-halo-penicillanates, 6,6-dihalopenam derivatives and (1S)-6-α-halopenicillanates sulfoxides by dimethyldioxirane asymmetric oxidation of the corresponding penicillanates and penam derivatives. This method is characterized by mild reactions conditions, short reaction times, excellent selectivity, very high yield, ease of reaction workup and complete avoidance of overoxidation products.

  我们描述了通过相应的青霉酸酯和二甲基二环氧乙烷烷不对称氧化制备（1R）-6,6-二卤代-，6β-卤代青霉酸酯，6,6-二卤代戊酰胺衍生物和（1S）-6-α-卤代青酸酯亚砜的便捷程序戊烷衍生物。该方法的特点是反应条件温和，反应时间短，选择性好，产率极高，反应后处理容易并且完全避免了过氧化产物的产生。
• Mata, Ernesto G.; Setti, Eduardo L.; Mascaretti, Oreste A., Journal of the Chemical Society. Perkin transactions I, 1988, p. 1551 - 1556
  作者：Mata, Ernesto G.、Setti, Eduardo L.、Mascaretti, Oreste A.、Boggio, Silvana B.、Roveri, Oscar A.

  DOI：——

  日期：——
• Synthesis and human leukocyte elastase inhibitory evaluation of phosphate triesters and acyl phosphates of penam sulfides and sulfones
  作者：Marı́a Laborde、Germán Pezzenati、Patricia Yovaldi、Oreste A. Mascaretti、Rolando C. Rossi、Juan Pablo Rossi

  DOI：10.1016/s0968-0896(01)00139-0

  日期：2001.8

  The synthesis of 6,6-dibromo-3 alpha-(diphenylphosphate)oxymethyl-2,2-dimethyl penam sulfone (3a), 6 alpha -chloro-3 alpha-(diphenylphosphate)oxymethyl-2,2-dimethyl penam sulfone (3b), benzyl 6 alpha-(diphenyl-phosphate)oxypenicillanate sulfone (4) and 6,6-dibromo-3 alpha-(methylphosphate)carbonyl-2,2-dimethylpenam sulfone (12) are reported. When tested as inhibitors of human leukocyte elastase, the compound 4 proved to be the most active. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Solid-phase based synthesis of biologically promising triazolyl aminoacyl (peptidyl) penicillins
  作者：Patricia G. Cornier、Dora B. Boggián、Ernesto G. Mata、Carina M.L. Delpiccolo

  DOI：10.1016/j.tetlet.2011.11.113

  日期：2012.2

  An efficient and versatile methodology for the preparation of valuable triazolyl aminoacyl (peptidyl) penicillins is described. Solid-phase Cu(I)-catalyzed Huisgen 1,3-dipolar cycloaddition was used as the key step showing general applicability and excellent regioselectivity either with CuI or [Cu(CH3CN)(4)]PF6 as Cu(I) source. (C) 2011 Elsevier Ltd. All rights reserved.