6,7-Dimethoxy-9-<2-ethyl>benzopentathiepin

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 6,7-Dimethoxy-9-<2-ethyl>benzopentathiepin
• 英文别名: Varacin N-trifluoroacetamide；N-[2-(6,7-dimethoxy-1,2,3,4,5-benzopentathiepin-9-yl)ethyl]-2,2,2-trifluoroacetamide
• 化学式: C₁₂H₁₂F₃NO₃S₅
• 分子量: 435.557
• InChiKey: YEEPUBGKTFYBHC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  174
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  5-溴香兰素 在 吡啶 、 喹啉 、 二氯化二硫 、 lithium aluminium tetrahydride 、 ammonium acetate 、 氨 、 溴 、 sodium 、 四丁基碘化铵 、 potassium carbonate 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 氯仿 、 溶剂黄146 为溶剂， 反应 0.08h， 生成 6,7-Dimethoxy-9-<2-ethyl>benzopentathiepin
  参考文献：
  名称：

  Synthesis of varacin, a cytotoxic naturally occurring benzopentathiepin isolated from a marine ascidian

  摘要：

  The total synthesis of varacin (1), a cytotoxic metabolite isolated from a marine ascidian, has been accomplished in 11 steps from vanillin, providing unambiguous confirmation of the unique dopamine-related benzopentathiepin structure.

  DOI：

  10.1021/jo00069a006

文献信息

• Synthesis and Structural Properties of the Benzopentathiepins Varacin and Isolissoclinotoxin A
  作者：Paul W. Ford、Mathew R. Narbut、Jack Belli、Bradley S. Davidson

  DOI：10.1021/jo00099a026

  日期：1994.10

  The unique pentathiepin-containing compounds varacin (1) and isolissoclinotoxin A (3) have each been synthesized in eight steps from vanillin. Formation of the pentathiepin ring in varacin was accomplished by treatment of the dithiolate anion, generated from the Na/NH3 reduction of bisbutyl sulfide intermediate 10, with 2 equiv of S2Cl2. Placement of the sulfur atoms on the aromatic ring was accomplished by treatment of 5,6-dibromovanillin (6) with cuprous n-butylmercaptide in pyridine/quinoline at 160 degrees C. The structure of the penultimate intermediate, TEOC-protected varacin (II), was confirmed by X-ray diffraction analysis. Isolissoclinotoxin A was prepared in an analogous manner, using a MOM group to protect the phenol. The structure of varacin has been confirmed; however, reductive acetylation of 3 yielded tetraacetate derivative 20, which was different than that reported as a product of lissoclinotoxin A acetylation. Because the data recorded for 20 did not match that previously reported, it is likely that the structure of lissoclinotoxin A should be reassigned to regioisomer 4, which has the phenol and methoxy group interchanged.
• 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.
• Varacin: a novel benzopentathiepin from Lissoclinum vareau that is cytotoxic toward a human colon tumor
  作者：Bradley S. Davidson、Tadeusz F. Molinski、Louis R. Barrows、Chris M. Ireland

  DOI：10.1021/ja00012a065

  日期：1991.6
• Synthesis of varacin, a cytotoxic naturally occurring benzopentathiepin isolated from a marine ascidian
  作者：Paul W. Ford、Bradley S. Davidson

  DOI：10.1021/jo00069a006

  日期：1993.8

  The total synthesis of varacin (1), a cytotoxic metabolite isolated from a marine ascidian, has been accomplished in 11 steps from vanillin, providing unambiguous confirmation of the unique dopamine-related benzopentathiepin structure.