Lissoclinotoxin A N-trifluoroacetamide | 1026308-53-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: Lissoclinotoxin A N-trifluoroacetamide
• 英文别名: 2,2,2-trifluoro-N-[2-(7-hydroxy-6-methoxy-1,2,3,4,5-benzopentathiepin-9-yl)ethyl]acetamide
• CAS: 1026308-53-1
• 化学式: C₁₁H₁₀F₃NO₃S₅
• 分子量: 421.531
• InChiKey: CXDSOPMVMMKPKK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  185
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  [¹³C]dioazomethane 、 Lissoclinotoxin A N-trifluoroacetamide 以 甲醇 为溶剂， 反应 2.0h， 生成 4-O-(13)CH3 Varacin N-trifluoroacetamide
  参考文献：
  名称：

  Five new alkaloids from the tropical ascidian, Lissoclinum sp. lissoclinotoxin A is chiral

  摘要：

  Five new alkaloids, lissoclin A (1), lissoclin B (2), Lissoclin C (3), lissoclinotoxin C (5), and the dimeric lissoclinotoxin D (6), were isolated along with the known compounds lissoclinotoxin A (4), 2-phenylethylamine (11), and 6-bromotryptamine (12) from Lissoclinum sp. collected from the Great Barrier Reef, Australia. Lissoclin A (1) undergoes photorearrangement to a new benzo-l,and oxathiazoline 10. The C-13 NMR spectrum of 4 is reported for the first time and the structure independently assigned by conversion to the known varacin N-trinuoroacetamide with diazomethane and [C-13]diazomethane. Compound 4 is chiral and exhibits unusual stereoisomerism due to restricted inversion about the benzopentathiepin ring. Lissoclinotoxin A (4) and D (6) exhibit antifungal activity against Candida albicans.

  DOI：

  10.1021/jo00101a018
• 作为产物：
  描述：

  Lissoclinotoxin A 、 三氟乙酸酐 以 二氯甲烷 为溶剂， 反应 0.17h， 生成 Lissoclinotoxin A N-trifluoroacetamide
  参考文献：
  名称：

  Five new alkaloids from the tropical ascidian, Lissoclinum sp. lissoclinotoxin A is chiral

  摘要：

  Five new alkaloids, lissoclin A (1), lissoclin B (2), Lissoclin C (3), lissoclinotoxin C (5), and the dimeric lissoclinotoxin D (6), were isolated along with the known compounds lissoclinotoxin A (4), 2-phenylethylamine (11), and 6-bromotryptamine (12) from Lissoclinum sp. collected from the Great Barrier Reef, Australia. Lissoclin A (1) undergoes photorearrangement to a new benzo-l,and oxathiazoline 10. The C-13 NMR spectrum of 4 is reported for the first time and the structure independently assigned by conversion to the known varacin N-trinuoroacetamide with diazomethane and [C-13]diazomethane. Compound 4 is chiral and exhibits unusual stereoisomerism due to restricted inversion about the benzopentathiepin ring. Lissoclinotoxin A (4) and D (6) exhibit antifungal activity against Candida albicans.

  DOI：

  10.1021/jo00101a018

文献信息

• Five new alkaloids from the tropical ascidian, Lissoclinum sp. lissoclinotoxin A is chiral
  作者：Philip A. Searle、Tadeusz F. Molinski

  DOI：10.1021/jo00101a018

  日期：1994.11

  Five new alkaloids, lissoclin A (1), lissoclin B (2), Lissoclin C (3), lissoclinotoxin C (5), and the dimeric lissoclinotoxin D (6), were isolated along with the known compounds lissoclinotoxin A (4), 2-phenylethylamine (11), and 6-bromotryptamine (12) from Lissoclinum sp. collected from the Great Barrier Reef, Australia. Lissoclin A (1) undergoes photorearrangement to a new benzo-l,and oxathiazoline 10. The C-13 NMR spectrum of 4 is reported for the first time and the structure independently assigned by conversion to the known varacin N-trinuoroacetamide with diazomethane and [C-13]diazomethane. Compound 4 is chiral and exhibits unusual stereoisomerism due to restricted inversion about the benzopentathiepin ring. Lissoclinotoxin A (4) and D (6) exhibit antifungal activity against Candida albicans.