methyl 2-diazo-3-oxo-9-undecynoate | 1067673-99-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2-diazo-3-oxo-9-undecynoate
• CAS: 1067673-99-7
• 化学式: C₁₂H₁₆N₂O₃
• 分子量: 236.271
• InChiKey: VYKZFAQKJJJDTQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.37
• 重原子数：
  17.0
• 可旋转键数：
  7.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  79.77
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  methyl 2-diazo-3-oxo-9-undecynoate 在 dirhodium tetraacetate 作用下， 以 二氯甲烷 为溶剂， 以75%的产率得到methyl 2-oxo-5-(3-pentynyl)cyclopentanecarboxylate
  参考文献：
  名称：

  Cyclization of Nonterminal Alkynic β-Keto Esters Catalyzed by Gold(I) Complex with a Semihollow, End-Capped Triethynylphosphine Ligand

  摘要：

  A cationic gold(l) complex with a semihollow-shaped trialkynylphosphine catalyzed 5-exo-dig and 6-endo-dig cyclizations of various internal alkynic beta-keto esters, showing a marked advantage over a gold(I)-PPh3 complex with respect to the rates of the reactions and the product yields. It is proposed that the gold-bound alkynic substrate in a catalytic pocket must be somewhat folded and that such a steric effect makes the carbon-carbon bond formation entropically more favorable.

  DOI：

  10.1021/ol802079r
• 作为产物：
  描述：

  methyl 3-oxo-9-undecynoate 在 三乙胺 、 甲烷磺酰基叠氮化物 作用下， 以 乙腈 为溶剂， 以95%的产率得到methyl 2-diazo-3-oxo-9-undecynoate
  参考文献：
  名称：

  Cyclization of Nonterminal Alkynic β-Keto Esters Catalyzed by Gold(I) Complex with a Semihollow, End-Capped Triethynylphosphine Ligand

  摘要：

  A cationic gold(l) complex with a semihollow-shaped trialkynylphosphine catalyzed 5-exo-dig and 6-endo-dig cyclizations of various internal alkynic beta-keto esters, showing a marked advantage over a gold(I)-PPh3 complex with respect to the rates of the reactions and the product yields. It is proposed that the gold-bound alkynic substrate in a catalytic pocket must be somewhat folded and that such a steric effect makes the carbon-carbon bond formation entropically more favorable.

  DOI：

  10.1021/ol802079r