methyl 4-(6-methylbenzo[d][1,3]dioxol-5-yl)-2-butynoate | 1189021-13-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: methyl 4-(6-methylbenzo[d][1,3]dioxol-5-yl)-2-butynoate
• 英文别名: Methyl 4-(6-methyl-1,3-benzodioxol-5-yl)but-2-ynoate
• CAS: 1189021-13-3
• 化学式: C₁₃H₁₂O₄
• 分子量: 232.236
• InChiKey: SUAVAHWIFJPWMA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 4-(6-methylbenzo[d][1,3]dioxol-5-yl)-2-butynoate 在 5% rhodium-on-charcoal 、 氢气 作用下， 以 甲醇 为溶剂， 反应 10.0h， 以96%的产率得到methyl 4-(6-methylbenzo[d][1,3]dioxol-5-yl)butanoate
  参考文献：
  名称：

  The Synthesis of Velloziolide via Nicholas Reaction Based γ-Carbonyl Cations

  摘要：

  The total synthesis of the 9,11-seco-rosane diterpene velloziolide (1) has been accomplished by employing the Nicholas reaction chemistry of 2a as a gamma-carbonyl cation equivalent. An initial model Study demonstrated the utility of Nicholas reactions of 2 in the generation of 4-arylalkynoate Co(2)(CO)(6) complexes, and in conjunction with Gilman cuprate addition and Johnson-Claisen rearrangement chemistry, the preparation of a 3-methyl-3-vinyl-4-arylalkanoate model for velloziolide. The Nicholas reaction/gamma-carbonyl cation methodology was then employed twice in the total synthesis to incorporate onto 3,4-methylenedioxytoluene the 4-carbon unit that became the gem-dimethyltetralin portion of the velloziolide and, subsequently, to incorporate the gamma-arylalkanoate function of the epsilon-lactone.

  DOI：

  10.1021/jo901471b
• 作为产物：
  描述：

  hexacarbonyl[μ-η4-(methyl 4-(6-methylbenzo[d][1,3]dioxol-5-yl)-2-butynoate)]dicobalt 在 碘 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以89%的产率得到methyl 4-(6-methylbenzo[d][1,3]dioxol-5-yl)-2-butynoate
  参考文献：
  名称：

  The Synthesis of Velloziolide via Nicholas Reaction Based γ-Carbonyl Cations

  摘要：

  The total synthesis of the 9,11-seco-rosane diterpene velloziolide (1) has been accomplished by employing the Nicholas reaction chemistry of 2a as a gamma-carbonyl cation equivalent. An initial model Study demonstrated the utility of Nicholas reactions of 2 in the generation of 4-arylalkynoate Co(2)(CO)(6) complexes, and in conjunction with Gilman cuprate addition and Johnson-Claisen rearrangement chemistry, the preparation of a 3-methyl-3-vinyl-4-arylalkanoate model for velloziolide. The Nicholas reaction/gamma-carbonyl cation methodology was then employed twice in the total synthesis to incorporate onto 3,4-methylenedioxytoluene the 4-carbon unit that became the gem-dimethyltetralin portion of the velloziolide and, subsequently, to incorporate the gamma-arylalkanoate function of the epsilon-lactone.

  DOI：

  10.1021/jo901471b

文献信息

• The Synthesis of Velloziolide via Nicholas Reaction Based γ-Carbonyl Cations
  作者：James R. Green、Andy A. Tjeng

  DOI：10.1021/jo901471b

  日期：2009.10.2

  The total synthesis of the 9,11-seco-rosane diterpene velloziolide (1) has been accomplished by employing the Nicholas reaction chemistry of 2a as a gamma-carbonyl cation equivalent. An initial model Study demonstrated the utility of Nicholas reactions of 2 in the generation of 4-arylalkynoate Co(2)(CO)(6) complexes, and in conjunction with Gilman cuprate addition and Johnson-Claisen rearrangement chemistry, the preparation of a 3-methyl-3-vinyl-4-arylalkanoate model for velloziolide. The Nicholas reaction/gamma-carbonyl cation methodology was then employed twice in the total synthesis to incorporate onto 3,4-methylenedioxytoluene the 4-carbon unit that became the gem-dimethyltetralin portion of the velloziolide and, subsequently, to incorporate the gamma-arylalkanoate function of the epsilon-lactone.