(E)-4-methoxy-2-butenal N,N-dimethylhydrazone | 143858-51-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (E)-4-methoxy-2-butenal N,N-dimethylhydrazone
• 英文别名: (E)-4-Methoxy-2-butenal N,N-Dimethylhydrazone；N-[[(E)-4-methoxybut-2-enylidene]amino]-N-methylmethanamine
• CAS: 143858-51-9
• 化学式: C₇H₁₄N₂O
• 分子量: 142.201
• InChiKey: KZMSPTVXOFKQKS-FKQQABSFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  24.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-溴-1,4-萘醌 、 (E)-4-methoxy-2-butenal N,N-dimethylhydrazone 以 xylene 为溶剂， 反应 6.0h， 以12%的产率得到4'-methoxycleistopholine
  参考文献：
  名称：

  Copyrine alkaloids: synthesis, spectroscopic characterization, and antimycotic/antimycobacterial activity of A- and B-ring-functionalized sampangines

  摘要：

  Several A- and B-ring-substituted sampangines were synthesized and evaluated for antifungal and antimycobacterial activity against AIDS-related opportunistic infection pathogens. Electrophilic halogenation provided a channel for structural elaboration of the sampangine B-ring at position 4, while the synthesis of A-ring 3-substituted sampangines and benzo[4,5]sampangine (24) were achieved from the corresponding functionalized cleistopholines. Two-dimensional NMR spectroscopy was used to rigorously characterize the A- and B-ring substituent patterns. Structure-activity relationship studies revealed the activity of the sampangines was enhanced by the presence of a substituent at position 3 or by a 4,5-benzo group.

  DOI：

  10.1021/jm00100a012
• 作为产物：
  描述：

  (Z)-4-methoxybut-2-en-1-ol 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 (E)-4-methoxy-2-butenal N,N-dimethylhydrazone
  参考文献：
  名称：

  Copyrine alkaloids: synthesis, spectroscopic characterization, and antimycotic/antimycobacterial activity of A- and B-ring-functionalized sampangines

  摘要：

  Several A- and B-ring-substituted sampangines were synthesized and evaluated for antifungal and antimycobacterial activity against AIDS-related opportunistic infection pathogens. Electrophilic halogenation provided a channel for structural elaboration of the sampangine B-ring at position 4, while the synthesis of A-ring 3-substituted sampangines and benzo[4,5]sampangine (24) were achieved from the corresponding functionalized cleistopholines. Two-dimensional NMR spectroscopy was used to rigorously characterize the A- and B-ring substituent patterns. Structure-activity relationship studies revealed the activity of the sampangines was enhanced by the presence of a substituent at position 3 or by a 4,5-benzo group.

  DOI：

  10.1021/jm00100a012

文献信息

• Compounds and compositions useful as antifungal and antimycobacterial
  申请人：The University of Mississippi

  公开号：US05227383A1

  公开（公告）日：1993-07-13

  New analogs of sampangine and cleistopholine, compositions and methods of preparation thereof, method of treating fungal and mycobacterial infections. The compounds have the general formula: ##STR1## where the R.sub.1, R.sub.2, and R.sub.5 groups are defined herein.

  新的sampangine和cleistopholine类似物，其组成和制备方法，以及治疗真菌和分枝杆菌感染的方法。该化合物具有以下通式：##STR1##其中R.sub.1，R.sub.2和R.sub.5基团在此定义。
• Antimycobacterial method
  申请人：The University of Mississippi

  公开号：US05530004A1

  公开（公告）日：1996-06-25

  New analogs of sampangine and cleistopholine, compositions and methods of preparation thereof, method of treating fungal and mycobacterial infections.

  新的sampangine和cleistopholine类似物，其组合物和制备方法，以及治疗真菌和分枝杆菌感染的方法。
• Copyrine alkaloids: synthesis, spectroscopic characterization, and antimycotic/antimycobacterial activity of A- and B-ring-functionalized sampangines
  作者：John R. Peterson、Jordan K. Zjawiony、Shihchih Liu、Charles D. Hufford、Alice M. Clark、Robin D. Rogers

  DOI：10.1021/jm00100a012

  日期：1992.10

  Several A- and B-ring-substituted sampangines were synthesized and evaluated for antifungal and antimycobacterial activity against AIDS-related opportunistic infection pathogens. Electrophilic halogenation provided a channel for structural elaboration of the sampangine B-ring at position 4, while the synthesis of A-ring 3-substituted sampangines and benzo[4,5]sampangine (24) were achieved from the corresponding functionalized cleistopholines. Two-dimensional NMR spectroscopy was used to rigorously characterize the A- and B-ring substituent patterns. Structure-activity relationship studies revealed the activity of the sampangines was enhanced by the presence of a substituent at position 3 or by a 4,5-benzo group.