4,5-Dimethoxy-7-<2-<<<2-(trimethylsilyl)ethoxy>carbonyl>amino>ethyl>benzotrithiole | 149625-18-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4,5-Dimethoxy-7-<2-<<<2-(trimethylsilyl)ethoxy>carbonyl>amino>ethyl>benzotrithiole
• 英文别名: 2-trimethylsilylethyl N-[2-(4,5-dimethoxy-1,2,3-benzotrithiol-7-yl)ethyl]carbamate
• CAS: 149625-18-3
• 化学式: C₁₆H₂₅NO₄S₃Si
• 分子量: 419.662
• InChiKey: PEROHPHAGFNTIO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.07
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  133
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4,5-Dimethoxy-7-<2-<<<2-(trimethylsilyl)ethoxy>carbonyl>amino>ethyl>benzotrithiole 在 三氟乙酸 作用下， 以 氯仿 为溶剂， 生成 varacin A
  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
• 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 作用下， 以 四氢呋喃 、 二氯甲烷 、 溶剂黄146 为溶剂， 生成 4,5-Dimethoxy-7-<2-<<<2-(trimethylsilyl)ethoxy>carbonyl>amino>ethyl>benzotrithiole
  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.
• 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.