<<<(4-methyl-1-phenyl-3-pentenyl)oxy>methyl>seleno>benzene | 153445-81-9

• 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: <<<(4-methyl-1-phenyl-3-pentenyl)oxy>methyl>seleno>benzene
• 英文别名: (4-Methyl-1-phenylpent-3-enoxy)methylselanylbenzene
• CAS: 153445-81-9
• 化学式: C₁₉H₂₂OSe
• 分子量: 345.343
• InChiKey: OGEUOVQKXNRDMQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.09
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  <<<(4-methyl-1-phenyl-3-pentenyl)oxy>methyl>seleno>benzene 生成 (2S)-2-phenyl-4-propan-2-yloxolane
  参考文献：
  名称：

  Rawal Viresh H., Singh Surendra P., Dufour Claire, Michoud Christophe, J. Org. Chem, 58 (1993) N 27, S 7718-7727

  摘要：

  DOI：
• 作为产物：
  描述：

  α-(三甲基硅氧基)苯乙腈 在 sodium tetrahydroborate 、 正丁基锂 、 sodium hydride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 为溶剂， 反应 6.83h， 生成 <<<(4-methyl-1-phenyl-3-pentenyl)oxy>methyl>seleno>benzene
  参考文献：
  名称：

  Scope of alkoxymethyl radical cyclizations

  摘要：

  We have explored different aspects of the cyclization capability of alkoxymethyl radicals and report here a full account of our investigations. The required radicals were generated from (phenylseleno)methyl ethers (e.g., 6), which were prepared from homoallylic or bis-homoallylic alcohols by a two-step process. The alcohols were alkylated with (iodomethyl)tributylstannane. The stannanes were reacted with n-BuLi, and the resulting alpha-alkoxyanions were trapped with diphenyldiselenide to give the (phenylseleno)methyl ethers, which were stable to chromatography. When treated with tributyltin hydride, in the presence of a radical initiator, these precursors undergo a smooth cyclization to substituted tetrahydrofurans and tetrahydropyrans. Formation of the cyclization product was found to be the primary pathway even at relatively high tin hydride concentration. The diastereoselectivity of this cyclization was comparable to that observed in other radical cyclizations. The cis selectivity in cyclization of 6 increased gradually (up to 11:1) as the reaction temperature was lowered. The cyclization can be used for the synthesis of bicyclic and tricyclic compounds and can be incorporated in systems capable of tandem cyclizations.

  DOI：

  10.1021/jo00079a016

文献信息

• Rawal Viresh H., Singh Surendra P., Dufour Claire, Michoud Christophe, J. Org. Chem, 58 (1993) N 27, S 7718-7727
  作者：Rawal Viresh H., Singh Surendra P., Dufour Claire, Michoud Christophe

  DOI：——

  日期：——
• Scope of alkoxymethyl radical cyclizations
  作者：Viresh H. Rawal、Surendra P. Singh、Claire Dufour、Christophe Michoud

  DOI：10.1021/jo00079a016

  日期：1993.12

  We have explored different aspects of the cyclization capability of alkoxymethyl radicals and report here a full account of our investigations. The required radicals were generated from (phenylseleno)methyl ethers (e.g., 6), which were prepared from homoallylic or bis-homoallylic alcohols by a two-step process. The alcohols were alkylated with (iodomethyl)tributylstannane. The stannanes were reacted with n-BuLi, and the resulting alpha-alkoxyanions were trapped with diphenyldiselenide to give the (phenylseleno)methyl ethers, which were stable to chromatography. When treated with tributyltin hydride, in the presence of a radical initiator, these precursors undergo a smooth cyclization to substituted tetrahydrofurans and tetrahydropyrans. Formation of the cyclization product was found to be the primary pathway even at relatively high tin hydride concentration. The diastereoselectivity of this cyclization was comparable to that observed in other radical cyclizations. The cis selectivity in cyclization of 6 increased gradually (up to 11:1) as the reaction temperature was lowered. The cyclization can be used for the synthesis of bicyclic and tricyclic compounds and can be incorporated in systems capable of tandem cyclizations.