(1Z,3Z)-2-[(tert-butyldimethylsilyl)oxy]-1,3-diphenoxy-4-(phenylthio)-1,3-butadiene | 181355-15-7

• 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: (1Z,3Z)-2-[(tert-butyldimethylsilyl)oxy]-1,3-diphenoxy-4-(phenylthio)-1,3-butadiene
• 英文别名: tert-butyl-[(1Z,3Z)-1,3-diphenoxy-4-phenylsulfanylbuta-1,3-dien-2-yl]oxy-dimethylsilane
• CAS: 181355-15-7
• 化学式: C₂₈H₃₂O₃SSi
• 分子量: 476.712
• InChiKey: BEPFRKLGTAIPPZ-FVNHVHOESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.64
• 重原子数：
  33
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  53
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-苯基马来酰亚胺 、 (1Z,3Z)-2-[(tert-butyldimethylsilyl)oxy]-1,3-diphenoxy-4-(phenylthio)-1,3-butadiene 以 xylene 为溶剂， 反应 48.0h， 以67%的产率得到(3aS,4S,7R,7aS)-5-(tert-Butyl-dimethyl-silanyloxy)-4,6-diphenoxy-2-phenyl-7-phenylsulfanyl-3a,4,7,7a-tetrahydro-isoindole-1,3-dione
  参考文献：
  名称：

  Synthesis and Diels−Alder Reactions of 4-Substituted- 1,3-diphenoxy-2-[(tert-butyldimethylsilyl)oxy]-1,3-butadienes:  Application to the Synthesis of Triaryl Ethers

  摘要：

  A novel class of tetrahetero-substituted 1,3-dienes 1a-d having aryl ether substituents at the 1,3-positions were synthesized by enol silylation of 4-substituted 1,3-diphenoxy-3-buten-2-ones-3a-c. The 1Z,3Z configuration of 1b has been assigned by X-ray crystallography. The synthesis of triaryl ethers utilizing a Diels-Alder approach involved reaction of diene la with methyl acrylate to furnish a 3:1 mixture of endo- and exo-adducts. Conversion of the adducts to cyclohexenone 8 and aromatization with DDQ gave triaryl ether 9. Cycloaddition reactions of la, Ib with some conjugated alkenes exhibited excellent regiospecificity and endo stereoselectivity.

  DOI：

  10.1021/jo960105d
• 作为产物：
  描述：

  4-(dimethylamino)-1,3-diphenoxy-3-buten-2-one 在 对甲苯磺酸 、 三乙胺 作用下， 以 乙醚 、 苯 为溶剂， 反应 7.5h， 生成 (1Z,3Z)-2-[(tert-butyldimethylsilyl)oxy]-1,3-diphenoxy-4-(phenylthio)-1,3-butadiene
  参考文献：
  名称：

  Synthesis and Diels−Alder Reactions of 4-Substituted- 1,3-diphenoxy-2-[(tert-butyldimethylsilyl)oxy]-1,3-butadienes:  Application to the Synthesis of Triaryl Ethers

  摘要：

  A novel class of tetrahetero-substituted 1,3-dienes 1a-d having aryl ether substituents at the 1,3-positions were synthesized by enol silylation of 4-substituted 1,3-diphenoxy-3-buten-2-ones-3a-c. The 1Z,3Z configuration of 1b has been assigned by X-ray crystallography. The synthesis of triaryl ethers utilizing a Diels-Alder approach involved reaction of diene la with methyl acrylate to furnish a 3:1 mixture of endo- and exo-adducts. Conversion of the adducts to cyclohexenone 8 and aromatization with DDQ gave triaryl ether 9. Cycloaddition reactions of la, Ib with some conjugated alkenes exhibited excellent regiospecificity and endo stereoselectivity.

  DOI：

  10.1021/jo960105d