6β-ethyl-7β-(3-formylindole-1-carbonyl)-2-azabicyclo[4.1.0]heptane-2-carboxylic acid 2-[2-(trimethylsilyl)ethyl] ester

• 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: 6β-ethyl-7β-(3-formylindole-1-carbonyl)-2-azabicyclo[4.1.0]heptane-2-carboxylic acid 2-[2-(trimethylsilyl)ethyl] ester
• 英文别名: 2-trimethylsilylethyl (1S,6R,7R)-6-ethyl-7-(3-formylindole-1-carbonyl)-2-azabicyclo[4.1.0]heptane-2-carboxylate
• 化学式: C₂₄H₃₂N₂O₄Si
• 分子量: 440.615
• InChiKey: BFHMBFZOSVYYFK-ZFGGDYGUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.06
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  68.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6β-ethyl-7β-(3-formylindole-1-carbonyl)-2-azabicyclo[4.1.0]heptane-2-carboxylic acid 2-[2-(trimethylsilyl)ethyl] ester 在 4 A molecular sieve 、 苄基三甲基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 8.33h， 生成 2-(3-ethyl-3,4,5,6-tetrahydropyridin-3-yl)-1-(3-vinylindol-1-yl)ethanone
  参考文献：
  名称：

  Intramolecular Imino Diels−Alder Reaction of a 3-Vinyl Indole:  Application to a Total Synthesis of (±)-Eburnamonine

  摘要：

  The intramolecular [4 + 2] cycloaddition of imine 1 has been examined under a variety of conditions including thermal; catalysis by acid, lithium cation, and Florisil; and the use of 5.0 M lithium perchlorate in diethyl ether. Cycloadduct 2 was transformed into (+/-)-eburnamonine 3 using acid catalysis. Substrate 1 was prepared by coupling indole-3-carboxaldehyde 7 with the activated p-nitrophenyl ester 9. Subsequent methylenation of 10 gave rise to 11, which upon exposure to fluoride ion provided imine 1.

  DOI：

  10.1021/jo9909960
• 作为产物：
  描述：

  3-ethylpiperidin-2-one 在 sodium hydroxide 、 草酰氯 、 lithium tri(t-butoxy)aluminum hydride 、 硫酸 、 铜 、 三乙胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 为溶剂， 反应 47.33h， 生成 6β-ethyl-7β-(3-formylindole-1-carbonyl)-2-azabicyclo[4.1.0]heptane-2-carboxylic acid 2-[2-(trimethylsilyl)ethyl] ester
  参考文献：
  名称：

  Intramolecular Imino Diels−Alder Reaction of a 3-Vinyl Indole:  Application to a Total Synthesis of (±)-Eburnamonine

  摘要：

  The intramolecular [4 + 2] cycloaddition of imine 1 has been examined under a variety of conditions including thermal; catalysis by acid, lithium cation, and Florisil; and the use of 5.0 M lithium perchlorate in diethyl ether. Cycloadduct 2 was transformed into (+/-)-eburnamonine 3 using acid catalysis. Substrate 1 was prepared by coupling indole-3-carboxaldehyde 7 with the activated p-nitrophenyl ester 9. Subsequent methylenation of 10 gave rise to 11, which upon exposure to fluoride ion provided imine 1.

  DOI：

  10.1021/jo9909960

文献信息

• Alkaloid Synthesis via Intramolecular Imino Diels-Alder Chemistry: Total Synthesis of (.+-.)-Eburnamonine
  作者：Michael D. Kaufman、Paul A. Grieco

  DOI：10.1021/jo00103a006

  日期：1994.12

  A novel strategy, featuring an intramolecular imino Diels-Alder reaction, for the construction of the pentacyclic framework of eburnamonine is detailed.
• Intramolecular Imino Diels−Alder Reaction of a 3-Vinyl Indole:  Application to a Total Synthesis of (±)-Eburnamonine
  作者：Paul A. Grieco、Michael D. Kaufman

  DOI：10.1021/jo9909960

  日期：1999.10.1

  The intramolecular [4 + 2] cycloaddition of imine 1 has been examined under a variety of conditions including thermal; catalysis by acid, lithium cation, and Florisil; and the use of 5.0 M lithium perchlorate in diethyl ether. Cycloadduct 2 was transformed into (+/-)-eburnamonine 3 using acid catalysis. Substrate 1 was prepared by coupling indole-3-carboxaldehyde 7 with the activated p-nitrophenyl ester 9. Subsequent methylenation of 10 gave rise to 11, which upon exposure to fluoride ion provided imine 1.