(Z)-5-[(8-(3-hydroxy-3-methyl-1-butynyl)-1-naphthyl)methylidene]-2,6-dimethyl-3-heptyne-2,6-diol | 205124-33-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (Z)-5-[(8-(3-hydroxy-3-methyl-1-butynyl)-1-naphthyl)methylidene]-2,6-dimethyl-3-heptyne-2,6-diol
• 英文别名: (5Z)-5-[[8-(3-hydroxy-3-methylbut-1-ynyl)naphthalen-1-yl]methylidene]-2,6-dimethylhept-3-yne-2,6-diol
• CAS: 205124-33-0
• 化学式: C₂₅H₂₈O₃
• 分子量: 376.496
• InChiKey: GNRGSIXNYDKAIV-FXBPSFAMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (Z)-5-[(8-(3-hydroxy-3-methyl-1-butynyl)-1-naphthyl)methylidene]-2,6-dimethyl-3-heptyne-2,6-diol 在 四(三苯基膦)钯 作用下， 以 乙腈 为溶剂， 生成 (E)-5-[(8-(3-hydroxy-3-methyl-1-butynyl)-1-naphthyl)methylidene]-2,6-dimethyl-3-heptyne-2,6-diol
  参考文献：
  名称：

  Steric Hindrance Facilitated Synthesis of Enynes and Their Intramolecular [4 + 2] Cycloaddition with Alkynes

  摘要：

  The palladium-catalyzed insertion of 1-alkynes into internal alkynes which are bent out of linearity by the interference with a peri or ortho substituent led to enynes regioselectively. The resulting enynes undergo a new type of intramolecular thermal cycloaddition, which can be used for the annulation of an aryl ring onto naphthalene derivatives to afford fluranthenes. The cyclization of (E)-1-(1-buten-3-ynyl)-8-ethynylnaphthalene could also be performed in the presence of a Cu(I) catalyst at room temperature.

  DOI：

  10.1021/jo9717853
• 作为产物：
  描述：

  1,8-二碘萘 在 copper(l) iodide 、 四(三苯基膦)钯 、 tris-(dibenzylideneacetone)dipalladium(0) 、 三苯基膦 四氢吡咯 、 三乙胺 、 silver(l) oxide 作用下， 以 甲苯 为溶剂， 反应 12.0h， 生成 (Z)-5-[(8-(3-hydroxy-3-methyl-1-butynyl)-1-naphthyl)methylidene]-2,6-dimethyl-3-heptyne-2,6-diol
  参考文献：
  名称：

  Steric Hindrance Facilitated Synthesis of Enynes and Their Intramolecular [4 + 2] Cycloaddition with Alkynes

  摘要：

  The palladium-catalyzed insertion of 1-alkynes into internal alkynes which are bent out of linearity by the interference with a peri or ortho substituent led to enynes regioselectively. The resulting enynes undergo a new type of intramolecular thermal cycloaddition, which can be used for the annulation of an aryl ring onto naphthalene derivatives to afford fluranthenes. The cyclization of (E)-1-(1-buten-3-ynyl)-8-ethynylnaphthalene could also be performed in the presence of a Cu(I) catalyst at room temperature.

  DOI：

  10.1021/jo9717853

文献信息

• Steric Hindrance Facilitated Synthesis of Enynes and Their Intramolecular [4 + 2] Cycloaddition with Alkynes
  作者：Juan J. González、Andrés Francesch、Diego J. Cárdenas、Antonio M. Echavarren

  DOI：10.1021/jo9717853

  日期：1998.5.1

  The palladium-catalyzed insertion of 1-alkynes into internal alkynes which are bent out of linearity by the interference with a peri or ortho substituent led to enynes regioselectively. The resulting enynes undergo a new type of intramolecular thermal cycloaddition, which can be used for the annulation of an aryl ring onto naphthalene derivatives to afford fluranthenes. The cyclization of (E)-1-(1-buten-3-ynyl)-8-ethynylnaphthalene could also be performed in the presence of a Cu(I) catalyst at room temperature.