ethyl 8-oxooct-2-ynoate | 130602-14-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl 8-oxooct-2-ynoate
• 英文别名: Ethyl 8-oxooct-2-ynoate
• CAS: 130602-14-1
• 化学式: C₁₀H₁₄O₃
• 分子量: 182.219
• InChiKey: XPBWGQALXAZNSF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 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：

  L-脯氨酸甲酯 、 ethyl 8-oxooct-2-ynoate 以 甲苯 为溶剂， 反应 1.5h， 以65%的产率得到9-ethyl 9a-methyl 2,3,4a,5,6,7,8,9a-octahydro-1H-pyrrolo[1,2-a]indole-9,9a-dicarboxylate
  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-(2-(triethylsilyloxy)-1-hydroxycyclohexyl)-2-diazoacetate 在 四氯化锡 作用下， 以 二氯甲烷 为溶剂， 以95%的产率得到ethyl 8-oxooct-2-ynoate
  参考文献：
  名称：

  Preparation of Tethered Aldehyde Ynoates and Ynones by Ring Fragmentation of Cyclic γ-Oxy-β-hydroxy-α-diazo Carbonyls

  摘要：

  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.

  DOI：

  10.1021/jo902405f

文献信息

• Intramolecular reductive cyclization of aldehydes and ketones with alkynes promoted by Samarium(II) iodide
  作者：Chul Shim Sang、Hwang Jin-Taik、Kang Han-Young、Ho Chang Moon

  DOI：10.1016/s0040-4039(00)97728-1

  日期：1990.1

  Samarium(II) iodide mediated intramolecular reductive coupling of carbonyl groups and alkynes in the presence of HMPA and t-BuOH was successfully performed to provide cyclized products. Some cyclic compounds containing a heteroatom such as oxygen or nitrogen were also efficiently prepared by this coupling reaction.

  在HMPA和t-BuOH存在下，成功地进行了碘化（（II）介导的羰基和炔烃的分子内还原偶联，以提供环化产物。通过该偶联反应，还可以有效地制备一些含杂原子的环化合物，例如氧或氮。
• 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。
• A Route to the C,D,E Ring System of the <i>Aspidosperma</i> Alkaloids
  作者：Geoffrey M. Giampa、Jian Fang、Matthias Brewer

  DOI：10.1021/acs.orglett.6b01674

  日期：2016.8.19

  A short synthetic sequence leading to the formation of the C,D,E-ring subunit of the Aspidosperma alkaloids is reported. This route is based on a ring fragmentation/intramolecular azomethine ylide 1,3-dipolar cycloaddition reaction sequence that gives the desired tricyclic product as a single diastereomer. A γ-amino-β-hydroxy-α-diazo carbonyl compound is shown to fragment in the presence of a Lewis

  报道了一个短的合成序列，该序列导致了曲霉植物生物碱的C，D，E环亚基的形成。该路线基于环断裂/分子内的甲亚胺基内酯1，3-偶极环加成反应序列，该序列给出所需的三环产物为单一非对映异构体。显示了在路易斯酸存在下，γ-氨基-β-羟基-α-重氮羰基化合物会断裂，从而生成可以直接还原为相应胺的亚胺产物。
• 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.
• 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.