2,3-Bis(n-butylthio)-4-(methoxymethoxy)-5-methoxybenzaldehyde | 158470-97-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,3-Bis(n-butylthio)-4-(methoxymethoxy)-5-methoxybenzaldehyde
• 英文别名: 2,3-Bis(butylsulfanyl)-5-methoxy-4-(methoxymethoxy)benzaldehyde
• CAS: 158470-97-4
• 化学式: C₁₈H₂₈O₄S₂
• 分子量: 372.55
• InChiKey: DGKGDRSZZAVIHK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  24
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  95.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  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 、 氯仿 为溶剂， 反应 25.25h， 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：

  2,3-二溴-4-羟基-5-甲氧基苯甲醛 、 alkaline earth salt of/the/ methylsulfuric acid 在 吡啶 、 喹啉 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.33h， 生成 2,3-Bis(n-butylthio)-4-(methoxymethoxy)-5-methoxybenzaldehyde
  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