6-Methoxy-7-(methoxymethoxy)-9-<2-<<<2-(trimethylsilyl)ethoxy>carbonyl>amino>ethyl>benzopentathiepin | 158471-02-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 6-Methoxy-7-(methoxymethoxy)-9-<2-<<<2-(trimethylsilyl)ethoxy>carbonyl>amino>ethyl>benzopentathiepin
• 英文别名: 2-trimethylsilylethyl N-[2-[7-methoxy-6-(methoxymethoxy)-1,2,3,4,5-benzopentathiepin-9-yl]ethyl]carbamate
• CAS: 158471-02-4
• 化学式: C₁₇H₂₇NO₅S₅Si
• 分子量: 513.821
• InChiKey: FTOLFVZGSPIQIQ-UHFFFAOYSA-N

物化性质

• 密度：
  1.277±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.34
• 重原子数：
  29
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  193
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  6-Methoxy-7-(methoxymethoxy)-9-<2-<<<2-(trimethylsilyl)ethoxy>carbonyl>amino>ethyl>benzopentathiepin 、 三氟乙酸 以 氯仿 为溶剂， 反应 1.0h， 以94%的产率得到Isolissoclinotoxin A trifluoroacetate
  参考文献：
  名称：

  Synthesis and Structural Properties of the Benzopentathiepins Varacin and Isolissoclinotoxin A

  摘要：

  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.

  DOI：

  10.1021/jo00099a026
• 作为产物：
  描述：

  2,3-Bis(n-butylthio)-4-(methoxymethoxy)-5-methoxybenzaldehyde 在 二氯化二硫 、 lithium aluminium tetrahydride 、 ammonium acetate 、 氨 、 sodium 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 24.25h， 生成 6-Methoxy-7-(methoxymethoxy)-9-<2-<<<2-(trimethylsilyl)ethoxy>carbonyl>amino>ethyl>benzopentathiepin
  参考文献：
  名称：

  Synthesis and Structural Properties of the Benzopentathiepins Varacin and Isolissoclinotoxin A

  摘要：

  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.

  DOI：

  10.1021/jo00099a026

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.