methyl 2-oxo-5-(3-pentynyl)cyclopentanecarboxylate | 1067674-14-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2-oxo-5-(3-pentynyl)cyclopentanecarboxylate
• 英文别名: Methyl 2-oxo-5-pent-3-ynylcyclopentane-1-carboxylate；methyl 2-oxo-5-pent-3-ynylcyclopentane-1-carboxylate
• CAS: 1067674-14-9
• 化学式: C₁₂H₁₆O₃
• 分子量: 208.257
• InChiKey: JZLRWLAYKYMGKG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 2-oxo-5-(3-pentynyl)cyclopentanecarboxylate 在 三苯基膦氯金 、 双三氟甲烷磺酰亚胺银盐 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 methyl 4-methyl-3-oxo-2,3,3a,6,7,7a-hexahydro-1H-indene-3a-carboxylate 、 (Z)-methyl 3-ethylidene-4-oxooctahydropentalene-3a-carboxylate
  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 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

文献信息

• Cyclization of Nonterminal Alkynic β-Keto Esters Catalyzed by Gold(I) Complex with a Semihollow, End-Capped Triethynylphosphine Ligand
  作者：Hideto Ito、Yusuke Makida、Atsuko Ochida、Hirohisa Ohmiya、Masaya Sawamura

  DOI：10.1021/ol802079r

  日期：2008.11.6

  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.