1-acetoxy-2,3-dimethyl-4-methoxy-6-(tri-n-butylstannyl)naphthalene | 168917-10-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-acetoxy-2,3-dimethyl-4-methoxy-6-(tri-n-butylstannyl)naphthalene
• CAS: 168917-10-0
• 化学式: C₂₇H₄₂O₃Sn
• 分子量: 533.339
• InChiKey: ZGEATJGOALFWOL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.45
• 重原子数：
  31.0
• 可旋转键数：
  12.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-环丁烯-1-酮,4-氯-2,3-二乙基- 、 1-acetoxy-2,3-dimethyl-4-methoxy-6-(tri-n-butylstannyl)naphthalene 在 tris(dibenzylideneacetone)dipalladium (0) 、 三(2-呋喃基)膦 作用下， 以 1,4-二氧六环 为溶剂， 反应 15.0h， 以77%的产率得到1-acetoxy-6,7-diethyl-2,3-dimethyl-5-hydroxy-4-methoxyphenanthrene
  参考文献：
  名称：

  General Synthetic Entry to Highly-Oxygenated, Angularly-Fused Polycyclic Aromatic Compounds

  摘要：

  A convergent and efficient synthesis of highly-oxygenated, angularly-fused polycyclic aromatic compounds has been developed. Nucleophilic addition of [4-(tri-n-butylstannyl)phenyl]lithium to a 3,4-disubstituted-cyclobutene-1,2-dione followed by appropriate protection of the hydroxyl group and thermal rearrangement of the O-protected addition product generated a 1,4-dioxygenated-2,3-disubstituted-6-(tri-n-butylstannyl) naphthalene. Stille coupling of the 6-(tri-n-butylstannyl)naphthalene with a 4-chloro-2,3-disubstituted-2-cyclobutenone and thermolysis of the coupled product gave highly-oxygenated phenanthrenes. An isomeric series of compounds was generated from [3-(tri-n-butylstannyl)phenyl]lithium. Substituted phenanthrenes at higher overall levels of oxygenation were prepared by (1) thermolysis of the adduct obtained by addition of a lithiated naphthalene, generated by Sn --> Li exchange from a 1,4-dioxygenated-2,3-disubstituted-6-(tri to a cyclobutenedione or (2) thermolysis of the double adducts generated by reaction of 2 equiv of a cyclobutenedione with either 1,4-dilithiobenzene or 1,3 dilithiobenzene. Phenanthrenes at lower levels of oxygenation were prepared by the palladium-catalyzed cross-coupling/thermolysis of 2 equivalents of a 4-chlorocyclobutenone with either 1,4-bis(tri-n-butylstannyl)benzene or 1,3-bis(tri-n-butylstannyl)benzene.

  DOI：

  10.1021/ja00117a009
• 作为产物：
  描述：

  1-acetoxy-2,3-dimethyl-4-hydroxy-6-(tri-n-butylstannyl)naphthalene 、 碘甲烷 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 以93%的产率得到1-acetoxy-2,3-dimethyl-4-methoxy-6-(tri-n-butylstannyl)naphthalene
  参考文献：
  名称：

  General Synthetic Entry to Highly-Oxygenated, Angularly-Fused Polycyclic Aromatic Compounds

  摘要：

  A convergent and efficient synthesis of highly-oxygenated, angularly-fused polycyclic aromatic compounds has been developed. Nucleophilic addition of [4-(tri-n-butylstannyl)phenyl]lithium to a 3,4-disubstituted-cyclobutene-1,2-dione followed by appropriate protection of the hydroxyl group and thermal rearrangement of the O-protected addition product generated a 1,4-dioxygenated-2,3-disubstituted-6-(tri-n-butylstannyl) naphthalene. Stille coupling of the 6-(tri-n-butylstannyl)naphthalene with a 4-chloro-2,3-disubstituted-2-cyclobutenone and thermolysis of the coupled product gave highly-oxygenated phenanthrenes. An isomeric series of compounds was generated from [3-(tri-n-butylstannyl)phenyl]lithium. Substituted phenanthrenes at higher overall levels of oxygenation were prepared by (1) thermolysis of the adduct obtained by addition of a lithiated naphthalene, generated by Sn --> Li exchange from a 1,4-dioxygenated-2,3-disubstituted-6-(tri to a cyclobutenedione or (2) thermolysis of the double adducts generated by reaction of 2 equiv of a cyclobutenedione with either 1,4-dilithiobenzene or 1,3 dilithiobenzene. Phenanthrenes at lower levels of oxygenation were prepared by the palladium-catalyzed cross-coupling/thermolysis of 2 equivalents of a 4-chlorocyclobutenone with either 1,4-bis(tri-n-butylstannyl)benzene or 1,3-bis(tri-n-butylstannyl)benzene.

  DOI：

  10.1021/ja00117a009