3,4-Bis(n-butylthio)-1-methoxy-2-(methoxymethoxy)-5-<2-<<<2-(trimethylsilyl)ethoxy>carbonyl>amino>ethyl>benzene | 158471-01-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3,4-Bis(n-butylthio)-1-methoxy-2-(methoxymethoxy)-5-<2-<<<2-(trimethylsilyl)ethoxy>carbonyl>amino>ethyl>benzene
• 英文别名: 2-trimethylsilylethyl N-[2-[2,3-bis(butylsulfanyl)-5-methoxy-4-(methoxymethoxy)phenyl]ethyl]carbamate
• CAS: 158471-01-3
• 化学式: C₂₅H₄₅NO₅S₂Si
• 分子量: 531.854
• InChiKey: VRIONRUTSVEJDN-UHFFFAOYSA-N

物化性质

• 沸点：
  597.2±50.0 °C(predicted)
• 密度：
  1.08±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.07
• 重原子数：
  34
• 可旋转键数：
  19
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  117
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3,4-Bis(n-butylthio)-1-methoxy-2-(methoxymethoxy)-5-<2-<<<2-(trimethylsilyl)ethoxy>carbonyl>amino>ethyl>benzene 在 二氯化二硫 、 氨 、 sodium 作用下， 以 氯仿 为溶剂， 反应 1.75h， 生成 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：

  3,4-Bis(n-butylthio)-1-methoxy-2-(methoxymethoxy)-5-(2-nitroethenyl)benzene 在 lithium aluminium tetrahydride 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 17.5h， 生成 3,4-Bis(n-butylthio)-1-methoxy-2-(methoxymethoxy)-5-<2-<<<2-(trimethylsilyl)ethoxy>carbonyl>amino>ethyl>benzene
  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.