4-hydroxy-1-methoxy-2-(1-methylethoxy)-3-phenyl-6-(tri-n-butylstannyl)naphthalene | 168917-36-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-hydroxy-1-methoxy-2-(1-methylethoxy)-3-phenyl-6-(tri-n-butylstannyl)naphthalene
• 英文别名: 4-Methoxy-2-phenyl-3-propan-2-yloxy-7-tributylstannylnaphthalen-1-ol
• CAS: 168917-36-0
• 化学式: C₃₂H₄₆O₃Sn
• 分子量: 597.425
• InChiKey: QPSDDMFEZUEYMP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.06
• 重原子数：
  36
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-hydroxy-1-methoxy-2-(1-methylethoxy)-3-phenyl-6-(tri-n-butylstannyl)naphthalene 、 碘甲烷 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 以95%的产率得到1,4-dimethoxy-2-(1-methylethoxy)-3-phenyl-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
• 作为产物：
  描述：

  4-methoxy-3-(1-methylethoxy)-2-phenyl-4[4'-(tri-n-butylstannyl)phenyl]-2-cyclobutene 以 xylene 为溶剂， 以71%的产率得到4-hydroxy-1-methoxy-2-(1-methylethoxy)-3-phenyl-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

文献信息

• General Synthetic Entry to Highly-Oxygenated, Angularly-Fused Polycyclic Aromatic Compounds
  作者：Sangho Koo、Lanny S. Liebeskind

  DOI：10.1021/ja00117a009

  日期：1995.3

  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.