3,3-diethyl-1-[2-(1H-indol-3-yl)ethyl]-2-piperidinone | 190378-18-8

• 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: 3,3-diethyl-1-[2-(1H-indol-3-yl)ethyl]-2-piperidinone
• 英文别名: 3,3-diethyl-1-[2-(1H-indol-3-yl)ethyl]piperidin-2-one
• CAS: 190378-18-8
• 化学式: C₁₉H₂₆N₂O
• 分子量: 298.428
• InChiKey: OFMMVDWJRQXATC-UHFFFAOYSA-N

物化性质

• 沸点：
  498.7±28.0 °C(Predicted)
• 密度：
  1.072±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  36.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3,3-diethyl-1-[2-(1H-indol-3-yl)ethyl]-2-piperidinone 在 bis(triphenylphosphine)carbonyliridium(I) chloride 、 1,1,3,3-四甲基二硅氧烷 作用下， 以 二氯甲烷 为溶剂， 以94%的产率得到
  参考文献：
  名称：

  铱催化的酰胺的铱催化的氮杂-螺环化反应：间断的Pictet-Spengler反应。

  摘要：

  描述了轻度还原吲哚连接的酰胺和内酰胺的螺环化，以有效和选择性地合成氮杂-螺环吲哚啉产物。Vaska络合物与四甲基二硅氧烷作为末端还原剂对叔酰胺或内酰胺的催化还原活化作用可引发亚胺离子的形成，然后引发栓系吲哚部分的非对映选择性5-内-trig螺环化。末端还原以整体高度化学选择性和非对映选择性的一锅法提供了氮杂螺并吲哚啉产品。

  DOI：

  10.1021/acs.orglett.9b02194
• 作为产物：
  描述：

  5-溴戊酸甲酯 在 正丁基锂 、 potassium carbonate 、 二异丙胺 、 potassium iodide 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 为溶剂， 反应 19.5h， 生成 3,3-diethyl-1-[2-(1H-indol-3-yl)ethyl]-2-piperidinone
  参考文献：
  名称：

  铱催化的酰胺的铱催化的氮杂-螺环化反应：间断的Pictet-Spengler反应。

  摘要：

  描述了轻度还原吲哚连接的酰胺和内酰胺的螺环化，以有效和选择性地合成氮杂-螺环吲哚啉产物。Vaska络合物与四甲基二硅氧烷作为末端还原剂对叔酰胺或内酰胺的催化还原活化作用可引发亚胺离子的形成，然后引发栓系吲哚部分的非对映选择性5-内-trig螺环化。末端还原以整体高度化学选择性和非对映选择性的一锅法提供了氮杂螺并吲哚啉产品。

  DOI：

  10.1021/acs.orglett.9b02194

文献信息

• Stereocontrolled Elaboration of Quaternary Carbon Centers through the Asymmetric Michael-Type Alkylation of Chiral Imines/Secondary Enamines:  Enantioselective Synthesis of (+)-Vincamine
  作者：Didier Desmaële、Khalid Mekouar、Jean d'Angelo

  DOI：10.1021/jo9622690

  日期：1997.6.13

  An enantioselective synthesis of (+)-vincamine (1) has been developed. The key strategic element was the stereocontrolled elaboration of a quaternary carbon center (future C-20 center of 1) by using the asymmetric Michael reaction involving chiral imines/secondary enamines under neutral conditions. Thus, addition of enaminolactam (S)-12, derived from ketolactam 7 (itself prepared in four steps from commercially available tryptamine) and (S)-1-phenylethylamine, to methyl acrylate led, after hydrolytic workup, to adduct (R)-6 with a 90% stereoselectivity. The critical removal of the additional keto group of 6 was then examined. After extensive experimentation, we finally established that the most efficient deoxygenation procedure was the Wolff-Kishner reduction of the corresponding keto acid, which proceeded with a 55% yield. The cornerstone [ABD]-tricyclic lactam ester 38 thus obtained was next cyclized under Bischler-Napieralski reaction conditions to afford, after catalytic hydrogenation of the intermediary iminium perchlorate salt, a mixture of the desired, known indoloquinolizidine 5 and its epimer 39, in a ratio of 6:1, respectively. Basic treatment of 5 led to (+)-homoeburnamonine 4, which was finally converted, according to a known procedure, into our goal (+)-vincamine (1). Thus, synthesis of (+)-vincamine (1) has been achieved by a linear sequence of 15 chemical operations, starting from tryptamine, with an overall yield of 1.2%.
• Iridium-Catalyzed Aza-Spirocyclization of Indole-Tethered Amides: An Interrupted Pictet–Spengler Reaction
  作者：Pablo Gabriel、Alex W. Gregory、Darren J. Dixon

  DOI：10.1021/acs.orglett.9b02194

  日期：2019.9.6

  A mild, reductive spirocyclization of indole-linked amides and lactams for the efficient and selective synthesis of aza-spirocyclic indoline products is described. The catalytic reductive activation of tertiary amides or lactams by Vaska's complex with tetramethyldisiloxane as the terminal reductant allowed iminium ion formation, before a diastereoselective 5-endo-trig spirocyclization of the tethered

  描述了轻度还原吲哚连接的酰胺和内酰胺的螺环化，以有效和选择性地合成氮杂-螺环吲哚啉产物。Vaska络合物与四甲基二硅氧烷作为末端还原剂对叔酰胺或内酰胺的催化还原活化作用可引发亚胺离子的形成，然后引发栓系吲哚部分的非对映选择性5-内-trig螺环化。末端还原以整体高度化学选择性和非对映选择性的一锅法提供了氮杂螺并吲哚啉产品。