7-carbomethoxy-7-(2-ethoxy-2-oxoethyl)-1,4-dioxaspiro[4,5]decan-8-one | 925688-14-8

• 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: 7-carbomethoxy-7-(2-ethoxy-2-oxoethyl)-1,4-dioxaspiro[4,5]decan-8-one
• 英文别名: Methyl 7-(2-ethoxy-2-oxoethyl)-8-oxo-1,4-dioxaspiro[4.5]decane-7-carboxylate
• CAS: 925688-14-8
• 化学式: C₁₄H₂₀O₇
• 分子量: 300.309
• InChiKey: VIOAXHZRRYSMBN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  88.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  7-carbomethoxy-7-(2-ethoxy-2-oxoethyl)-1,4-dioxaspiro[4,5]decan-8-one 在 三氟乙酸 作用下， 以 二氯甲烷 、 xylene 为溶剂， 反应 24.33h， 生成 methyl 1-(3-(5-methylfuran-2-yl)propyl)-2,5-dioxo-2,3,3a,4,5,6-hexahydro-1H-indole-3a-carboxylate
  参考文献：
  名称：

  Acid-Promoted Cyclization Reactions of Tetrahydroindolinones. Model Studies for Possible Application in a Synthesis of Selaginoidine

  摘要：

  [GRAPHIC]The synthesis of various substituted bicyclic lactams by an acid-induced Pictet-Spengler reaction of tetrahydroindolinones bearing tethered heteroaromatic rings is presented. The outcome of the cyclization depends on the position of the furan tether, tether length, nature of the tethered heteroaromatic ring, and the substituent group present on the 5-position of the tethered heteroaryl group. A one-pot procedure was developed to efficiently prepare tetrahydroindolinones containing tethered furan rings. In a typical example, the reaction of furanyl azide 26 with n-Bu3P delivered iminophosphorane 27, which was allowed to react with a 1-alkyl-(2-oxocyclohexyl)acetic acid to provide the desired furanyl-substituted tetrahydroindolinone system 29. Treatment of 29 with trifluoroacetic acid afforded the tetracyclic lactam skeleton 30 found in the alkaloid (+/-)-selaginoidine.

  DOI：

  10.1021/jo0619783
• 作为产物：
  描述：

  1,4-环己二酮单乙二醇缩酮 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 27.0h， 生成 7-carbomethoxy-7-(2-ethoxy-2-oxoethyl)-1,4-dioxaspiro[4,5]decan-8-one
  参考文献：
  名称：

  Acid-Promoted Cyclization Reactions of Tetrahydroindolinones. Model Studies for Possible Application in a Synthesis of Selaginoidine

  摘要：

  [GRAPHIC]The synthesis of various substituted bicyclic lactams by an acid-induced Pictet-Spengler reaction of tetrahydroindolinones bearing tethered heteroaromatic rings is presented. The outcome of the cyclization depends on the position of the furan tether, tether length, nature of the tethered heteroaromatic ring, and the substituent group present on the 5-position of the tethered heteroaryl group. A one-pot procedure was developed to efficiently prepare tetrahydroindolinones containing tethered furan rings. In a typical example, the reaction of furanyl azide 26 with n-Bu3P delivered iminophosphorane 27, which was allowed to react with a 1-alkyl-(2-oxocyclohexyl)acetic acid to provide the desired furanyl-substituted tetrahydroindolinone system 29. Treatment of 29 with trifluoroacetic acid afforded the tetracyclic lactam skeleton 30 found in the alkaloid (+/-)-selaginoidine.

  DOI：

  10.1021/jo0619783

文献信息

• Acid-Promoted Cyclization Reactions of Tetrahydroindolinones. Model Studies for Possible Application in a Synthesis of Selaginoidine
  作者：Mickea D. Rose、Michael P. Cassidy、Paitoon Rashatasakhon、Albert Padwa

  DOI：10.1021/jo0619783

  日期：2007.1.1

  [GRAPHIC]The synthesis of various substituted bicyclic lactams by an acid-induced Pictet-Spengler reaction of tetrahydroindolinones bearing tethered heteroaromatic rings is presented. The outcome of the cyclization depends on the position of the furan tether, tether length, nature of the tethered heteroaromatic ring, and the substituent group present on the 5-position of the tethered heteroaryl group. A one-pot procedure was developed to efficiently prepare tetrahydroindolinones containing tethered furan rings. In a typical example, the reaction of furanyl azide 26 with n-Bu3P delivered iminophosphorane 27, which was allowed to react with a 1-alkyl-(2-oxocyclohexyl)acetic acid to provide the desired furanyl-substituted tetrahydroindolinone system 29. Treatment of 29 with trifluoroacetic acid afforded the tetracyclic lactam skeleton 30 found in the alkaloid (+/-)-selaginoidine.