3-(1-benzyl-3-ethyl-2-oxopiperidin-3-yl)propionitrile | 1005156-21-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 3-(1-benzyl-3-ethyl-2-oxopiperidin-3-yl)propionitrile
• 英文别名: 3-(1-Benzyl-3-ethyl-2-oxopiperidin-3-yl)propanenitrile
• CAS: 1005156-21-7
• 化学式: C₁₇H₂₂N₂O
• 分子量: 270.374
• InChiKey: ORIKMKOUBXGZIY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(1-benzyl-3-ethyl-2-oxopiperidin-3-yl)propionitrile 在 溴 、 铜 、 potassium carbonate 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 13.5h， 生成 (E)-methyl 2-bromo-3-(2-(3-(2-cyanoethyl)-3-ethyl-2-oxopiperidin-1-yl)phenyl)acrylate
  参考文献：
  名称：

  Total Synthesis of (±)-Goniomitine via Radical Translocation

  摘要：

  The aspidosperma alkaloid goniomitine was synthesized in six steps from 2-ethyl-delta-valerolactam. The convergent strategy features an Ullman coupling to assemble the required carbon atoms. A complexity-generating radical translocation reaction was used to build the indole architecture.

  DOI：

  10.1021/acs.orglett.5b02277
• 作为产物：
  描述：

  3-ethyl-1-(phenylmethyl)-2-piperidinone 、 丙烯腈 在 三氟甲磺酸三甲基硅酯 、 三乙胺 、 zinc(II) chloride 作用下， 以 二氯甲烷 为溶剂， 以63%的产率得到3-(1-benzyl-3-ethyl-2-oxopiperidin-3-yl)propionitrile
  参考文献：
  名称：

  Total Synthesis of (±)-Goniomitine via Radical Translocation

  摘要：

  The aspidosperma alkaloid goniomitine was synthesized in six steps from 2-ethyl-delta-valerolactam. The convergent strategy features an Ullman coupling to assemble the required carbon atoms. A complexity-generating radical translocation reaction was used to build the indole architecture.

  DOI：

  10.1021/acs.orglett.5b02277

文献信息

• Total Synthesis of (±)-Goniomitine via a Formal Nitrile/Donor−Acceptor Cyclopropane [3 + 2] Cyclization
  作者：Christian L. Morales、Brian L. Pagenkopf

  DOI：10.1021/ol702376j

  日期：2008.1.1

  The total synthesis of (+/-)-goniomitine has been accomplished in 17 linear steps with 5.2% overall yield starting from commercially available delta-valerolactam. A synthetic highlight includes the first application of a formal [3 + 2] cycloaddition between a highly functionalized nitrile and a donor-acceptor cyclopropane to prepare an indole nucleus. The use of a microwave reactor is shown to greatly

  （+/-）-goniomitine的总合成已从17个线性步骤完成，从市售的delta-valerolactam开始，总产率为5.2％。合成亮点包括首次在高度官能化的腈与供体-受体环丙烷之间进行正式的[3 + 2]环加成反应，以制备吲哚核。微波反应器的使用显示出大大改善了两个步骤的反应时间。
• Total Synthesis of (±)-Quebrachamine via [3+2] Cycloaddition and Efficient Chloroacetamide Photocyclization
  作者：Barbora Bajtos、Brian L. Pagenkopf

  DOI：10.1002/ejoc.200801154

  日期：2009.3

  The total synthesis of (±)-quebrachamine has been completed in 13 linear steps and 17.8 % overall yield. The indole core was constructed via a formal [3+2] dipolar cycloaddition between a functionalized nitrile and donor-acceptor cyclopropane, and the synthetically challenging nine-membered ring was secured by an efficient chloroacetamide photocyclization.(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451

  (±)-quebrachamine 的全合成已在 13 个线性步骤中完成，总产率为 17.8%。吲哚核心是通过功能化腈和供体-受体环丙烷之间的正式 [3+2] 偶极环加成构建的，具有合成挑战性的九元环通过有效的氯乙酰胺光环化作用得到保护。 (© Wiley-VCH Verlag GmbH & Co . KGaA, 69451 德国魏因海姆, 2009)
• Total Synthesis of (±)-Goniomitine via Radical Translocation
  作者：Jessica K. Vellucci、Christopher M. Beaudry

  DOI：10.1021/acs.orglett.5b02277

  日期：2015.9.18

  The aspidosperma alkaloid goniomitine was synthesized in six steps from 2-ethyl-delta-valerolactam. The convergent strategy features an Ullman coupling to assemble the required carbon atoms. A complexity-generating radical translocation reaction was used to build the indole architecture.