9-氧代-2-炔酸乙酯 | 1017590-76-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 9-氧代-2-炔酸乙酯
• 英文名称: ethyl 9-oxonon-2-ynoate
• 英文别名: Ethyl 9-oxonon-2-ynoate
• CAS: 1017590-76-9
• 化学式: C₁₁H₁₆O₃
• 分子量: 196.246
• InChiKey: OFTXHXJFKYKRKJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.64
• 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：

  9-氧代-2-炔酸乙酯 、 L-proline trimethylsilyl ester 以 甲苯 为溶剂， 反应 1.0h， 以44%的产率得到ethyl 1,2,3,4a,5,6,7,8,9,10a-decahydrocyclohepta[b]pyrrolizine-10-carboxylate
  参考文献：
  名称：

  An Efficient Synthetic Approach to Polycyclic 2,5-Dihydropyrroles from α-Silyloxy Ketones

  摘要：

  A three-step sequence to prepare polycyclic 2,5-dihydropyrroles from alpha-silyloxy ketones is presented. A Lewis acid-mediated ring fragmentation of cyclic gamma-sjlyloxy-beta-hydroxy-alpha-diazo esters provided tethered aldehyde ynoate intermediates which, when treated with amino acid silyl esters, underwent intramolecular azomethine ylide 1,3-dipolar cycloadditions. The 2,5-dihydropyrrole products were formed in good to excellent yield as single diastereomers.

  DOI：

  10.1021/jo901978y
• 作为产物：
  描述：

  ethyl 2-(trans-2-(tert-butyldimethylsilyloxy)-1-hydroxycycloheptyl)-2-diazoacetate 在 四氯化锡 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以76%的产率得到9-氧代-2-炔酸乙酯
  参考文献：
  名称：

  路易斯酸促进γ-甲硅烷氧基-β-羟基-α-重氮酯的碳-碳键断裂

  摘要：

  当用四氯化锡处理时，环状 γ-甲硅烷氧基-β-羟基-α-重氮酯会有效地断裂 Cbeta-Cgamma 键，以提供高产率的束缚醛 ynoate 产品。

  DOI：

  10.1021/ja801004d

文献信息

• Preparation of Tethered Aldehyde Ynoates and Ynones by Ring Fragmentation of Cyclic γ-Oxy-β-hydroxy-α-diazo Carbonyls
  作者：Ali Bayir、Cristian Draghici、Matthias Brewer

  DOI：10.1021/jo902405f

  日期：2010.1.15

  Cyclic gamma-oxy-beta-hydroxy-alpha-diazo carbonyls undergo Lewis acid induced ring fragmentation to provide either ynoates or ynones tethered to an aldehyde, ketone, or ester. The fragmentation precursors are convenient to prepare by adding lithiated alpha-diazo carbonyls to alpha-oxy ketones. The fragmentation appears general and provides a variety of functional group-rich products in good to excellent yield.
• Lewis Acid Promoted Carbon−Carbon Bond Cleavage of γ-Silyloxy-β-hydroxy-α-diazoesters
  作者：Cristian Draghici、Matthias Brewer

  DOI：10.1021/ja801004d

  日期：2008.3.1

  Cyclic gamma-silyloxy-beta-hydroxy-alpha-diazoesters undergo efficient rupture of the Cbeta-Cgamma bond when treated with tin tetrachloride to provide tethered aldehyde ynoate products in high yield.

  当用四氯化锡处理时，环状 γ-甲硅烷氧基-β-羟基-α-重氮酯会有效地断裂 Cbeta-Cgamma 键，以提供高产率的束缚醛 ynoate 产品。
• An Efficient Synthetic Approach to Polycyclic 2,5-Dihydropyrroles from α-Silyloxy Ketones
  作者：Cristian Draghici、Qiufeng Huang、Matthias Brewer

  DOI：10.1021/jo901978y

  日期：2009.11.6

  A three-step sequence to prepare polycyclic 2,5-dihydropyrroles from alpha-silyloxy ketones is presented. A Lewis acid-mediated ring fragmentation of cyclic gamma-sjlyloxy-beta-hydroxy-alpha-diazo esters provided tethered aldehyde ynoate intermediates which, when treated with amino acid silyl esters, underwent intramolecular azomethine ylide 1,3-dipolar cycloadditions. The 2,5-dihydropyrrole products were formed in good to excellent yield as single diastereomers.