(3S,3aS,5S,6aR)-3a,4,4-trimethyl-2-oxohexahydro-3,5-methanocyclopenta[b]pyrrole-1(2H)-sulfonyl chloride | 1255716-94-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (3S,3aS,5S,6aR)-3a,4,4-trimethyl-2-oxohexahydro-3,5-methanocyclopenta[b]pyrrole-1(2H)-sulfonyl chloride
• CAS: 1255716-94-9
• 化学式: C₁₁H₁₆ClNO₃S
• 分子量: 277.772
• InChiKey: NUVQJUDQCSZTDK-PRKAOEEVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.75
• 重原子数：
  17.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  54.45
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  (1R,2R,5S,7R)-2,8,8-trimethyl-4-oxo-3-azatricyclo[5.1.1.02,5]nonane-3-sulfonyl chloride 以 正己烷 为溶剂， 生成 (3S,3aS,5S,6aR)-3a,4,4-trimethyl-2-oxohexahydro-3,5-methanocyclopenta[b]pyrrole-1(2H)-sulfonyl chloride
  参考文献：
  名称：

  Synthesis, Antimicrobial Evaluation, and Structure–Activity Relationship of α-Pinene Derivatives

  摘要：

  Several (+)- and (-)-alpha-pinene derivatives were synthesized and evaluated for their antimicrobial activity toward Gram-positive bacteria Micrococcus luteus and Staphylococcus aureus, Gram-negative bacterium Escherichia coli, and the unicellular fungus Candida albicans using bioautographic assays. (+)-alpha-Pinene 1a showed modest activity against the test organisms, whereas (-)-alpha-pinene 1b showed no activity at the tested concentration. Of all the alpha-pinene derivatives evaluated, the beta-lactam derivatives (10a and 10b) were the most antimicrobial. The increase in the antimicrobial activity of 10a compared to la ranged from nearly 3.5-fold (C. albicans) to 43-fold (S. aureus). The mean +/- standard deviation for the zone of inhibition (mm) for 10a (C. albicans) was 31.9 +/- 4.3 and that for S. aureus was 51.1 +/- 2.9. Although (-)-alpha-pinene 1b was not active toward the test microorganisms, the corresponding beta-lactam 10b, amino ester 13b, and amino alcohol 14b showed antimicrobial activity toward the test microorganisms. The increase in the antimicrobial activity of lob compared to 1b ranged from 32-fold (S. aureus) to 73-fold (M. luteus). The mean +/- standard deviation for the zone of inhibition (mm) for 10b (S. aureus) was 32.0 +/- 0.60 and that for M. luteus was 73.2 +/- 0.30.

  DOI：

  10.1021/jf403586t

文献信息

• Addition products of chlorosulfonylisocyanate to (+)-3-carene and α-pinene enantiomers
  作者：F. Z. Makaev、L. A. Vlad、L. P. Bets、S. T. Malinovskii、K. N. Gavrilov、M. Gdanets

  DOI：10.1007/s10600-010-9669-3

  日期：2010.9

  Optically active lactams were synthesized from (+)-3-carene and α-pinene enantiomers. Their properties and structures were characterized. A pathway for preparing their trifluoroacetate salts was demonstrated.

  由(+)-3-蒈烯和α-蒎烯对映体合成光学活性内酰胺。对它们的性质和结构进行了表征。证明了制备其三氟乙酸盐的途径。