1-[3-(furan-2-yl)-propyl]-3a-methyl-1,3,4,4a,5,6-hexahydroindol-2-one | 651315-22-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 1-[3-(furan-2-yl)-propyl]-3a-methyl-1,3,4,4a,5,6-hexahydroindol-2-one
• 英文别名: 1-(3-furan-2-yl-propyl)-3a-methyl-1,3,3a,4,5,6-hexahydroindol-2-one；1-[3-(Furan-2-yl)propyl]-3a-methyl-3,4,5,6-tetrahydroindol-2-one
• CAS: 651315-22-9
• 化学式: C₁₆H₂₁NO₂
• 分子量: 259.348
• InChiKey: JFYSVHMUBDYPMW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  33.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-[3-(furan-2-yl)-propyl]-3a-methyl-1,3,4,4a,5,6-hexahydroindol-2-one 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以54%的产率得到
  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：

  3-(2-呋喃基)丙烷-1-草酸铵 、 2-(1-甲基-2-氧代环己基)乙酸 以 xylene 为溶剂， 反应 1.0h， 以81%的产率得到1-[3-(furan-2-yl)-propyl]-3a-methyl-1,3,4,4a,5,6-hexahydroindol-2-one
  参考文献：
  名称：

  使用NBS促进的六氢吲哚满酮衍生物的环化反应，可以高效合成（+/-）-异戊s啶。

  摘要：

  NBS促进的六氢吲哚满酮衍生物的分子内亲电芳族取代反应用于组装赤藓烷骨架的四环核。在另外三个步骤中，将所得的环化产物转化为（+/-）-异戊酰胺。使用各种取代的芳基和呋喃基双环内酰胺在酸性条件下，环化反应也很成功。[反应：看文字]

  DOI：

  10.1021/ol036106r

文献信息

• Efficient Synthesis of (±)-Erysotramidine Using an NBS-Promoted Cyclization Reaction of a Hexahydroindolinone Derivative
  作者：Hyoung Ik Lee、Michael P. Cassidy、Paitoon Rashatasakhon、Albert Padwa

  DOI：10.1021/ol036106r

  日期：2003.12.1

  An NBS-promoted intramolecular electrophilic aromatic substitution reaction of a hexahydroindolinone derivative was used to assemble the tetracyclic core of the erythrinane skeleton. The resulting cyclized product was transformed into (+/-)-erysotramidine in three additional steps. The cyclization reaction is also successful using variously substituted aryl and furanyl bicyclic lactams under acidic

  NBS促进的六氢吲哚满酮衍生物的分子内亲电芳族取代反应用于组装赤藓烷骨架的四环核。在另外三个步骤中，将所得的环化产物转化为（+/-）-异戊酰胺。使用各种取代的芳基和呋喃基双环内酰胺在酸性条件下，环化反应也很成功。[反应：看文字]
• 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.