1-<(E)-1-(Methylthio)hexen-2-yl>-2-(methoxymethoxy)naphthalene | 151504-74-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-<(E)-1-(Methylthio)hexen-2-yl>-2-(methoxymethoxy)naphthalene
• 英文别名: 2-(methoxymethoxy)-1-[(E)-1-methylsulfanylhex-1-en-2-yl]naphthalene
• CAS: 151504-74-4
• 化学式: C₁₉H₂₄O₂S
• 分子量: 316.464
• InChiKey: ZJSPDAIQKYMMAB-DTQAZKPQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  43.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-<(E)-1-(Methylthio)hexen-2-yl>-2-(methoxymethoxy)naphthalene 在 盐酸 、 mercury(II) trifluoroacetate 、 镍 作用下， 以 甲醇 为溶剂， 反应 12.0h， 生成 1-Butylnaphtho<2,1-b>furan
  参考文献：
  名称：

  Convenient one-pot synthesis of vinylic sulfides from thioalkynes via a catalytic hydroboration-coupling sequence

  摘要：

  A variety of vinylic sulfides are stereospecifically synthesized by the catalytic hydroboration of thioacetylenes with catecholborane followed by cross-coupling of the resulting boron derivatives with organic halides. The use of the same palladium catalyst for both stages allows the whole transformation to be carried out in one flask. The synthetic utility of the method is demonstrated by the transformation of vinylic sulfides into diene, indole, and naphtho[b]furan derivatives.

  DOI：

  10.1021/jo00072a015
• 作为产物：
  描述：

  1-(methylthio)-1-hexyne 、 1-碘-2-(甲氧基甲氧基)萘 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride sodium hydroxide 、 儿萘酚硼烷 作用下， 生成 1-<(E)-1-(Methylthio)hexen-2-yl>-2-(methoxymethoxy)naphthalene
  参考文献：
  名称：

  Convenient one-pot synthesis of vinylic sulfides from thioalkynes via a catalytic hydroboration-coupling sequence

  摘要：

  A variety of vinylic sulfides are stereospecifically synthesized by the catalytic hydroboration of thioacetylenes with catecholborane followed by cross-coupling of the resulting boron derivatives with organic halides. The use of the same palladium catalyst for both stages allows the whole transformation to be carried out in one flask. The synthetic utility of the method is demonstrated by the transformation of vinylic sulfides into diene, indole, and naphtho[b]furan derivatives.

  DOI：

  10.1021/jo00072a015

文献信息

• Convenient one-pot synthesis of vinylic sulfides from thioalkynes via a catalytic hydroboration-coupling sequence
  作者：Ilya D. Gridnev、Norio Miyaura、Akira Suzuki

  DOI：10.1021/jo00072a015

  日期：1993.9

  A variety of vinylic sulfides are stereospecifically synthesized by the catalytic hydroboration of thioacetylenes with catecholborane followed by cross-coupling of the resulting boron derivatives with organic halides. The use of the same palladium catalyst for both stages allows the whole transformation to be carried out in one flask. The synthetic utility of the method is demonstrated by the transformation of vinylic sulfides into diene, indole, and naphtho[b]furan derivatives.