tert-butyl (2-oxo-5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1(2H)-ylidene)carbamate | 1606996-78-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: tert-butyl (2-oxo-5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1(2H)-ylidene)carbamate
• CAS: 1606996-78-4
• 化学式: C₁₆H₁₈N₂O₃
• 分子量: 286.331
• InChiKey: IMNZHGUZZIWAJS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  21.0
• 可旋转键数：
  0.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  58.97
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  硝基甲烷 、 tert-butyl (2-oxo-5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1(2H)-ylidene)carbamate 在 C₄₉H₄₅ClN₅Ni⁽¹⁺⁾*Cl^(1-) 、 N,N-二异丙基乙胺 作用下， 以 甲苯 为溶剂， 反应 14.5h， 以97%的产率得到(R)-tert-butyl (1-(nitromethyl)-2-oxo-2,4,5,6-tetrahydro-1H-pyrrolo[3,2,1-ij]quinolin-1-yl)carbamate
  参考文献：
  名称：

  Bis(imidazolidine)pyridine-NiCl₂ Catalyst for Nitro-Mannich Reaction of Isatin-Derived N-Boc Ketimines: Asymmetric Synthesis of Chiral 3-Substituted 3-Amino-2-oxindoles

  摘要：

  An (S,S)-diphenyldiamine-derived bis(imidazolidine)-pyridine (PyBidine)-NiCl2 complex catalyzed the nitro-Mannich reaction of isatin-derived N-Boc ketimines to construct a chiral quaternary aminocarbon center at the C3 position of oxindoles in yields of up to 99% with 95% ee.

  DOI：

  10.1021/ol501085y

文献信息

• Chiral Guanidine/Copper Catalyzed Asymmetric Azide‐Alkyne Cycloaddition/[2+2] Cascade Reaction
  作者：Songsong Guo、Pei Dong、Yushuang Chen、Xiaoming Feng、Xiaohua Liu

  DOI：10.1002/anie.201810679

  日期：2018.12.17

  copper(I) catalyst for the asymmetric azide‐alkyne cycloaddition/[2+2] cascade reaction. Optically active spiroazetidinimine oxindoles were constructed by trapping the ketenimine species under mild reaction conditions. High level of enantioinduction and excellent isolated yields were achieved in the three‐component reaction of various isatin‐derived ketimines, sulfonyl azides, and terminal alkynes. Control

  我们报告了不对称叠氮化物-炔烃环加成/ [2 + 2]级联反应的手性胍基铜（I）催化剂的开发。通过在温和的反应条件下捕获酮亚胺物种来构建旋光性螺氮杂环丁胺亚胺吲哚。在各种源自异黄素的酮亚胺，磺酰叠氮化物和末端炔烃的三组分反应中，实现了高水平的对映体诱导和出色的分离产率。使用对照实验和X射线晶体学研究手性胍盐与铜盐的相互作用。
• PyBidine–NiCl₂-Catalyzed Asymmetric Addition of Alcohols and Peroxides to Isatin-Derived Ketimines
  作者：Takayoshi Arai、Kento Tsuchiya、Eri Matsumura

  DOI：10.1021/acs.orglett.5b00928

  日期：2015.5.15

  An (S,S)-diphenyldiamine-derived bis(imidazolidine)pyridine (PyBidine)-NiCl2 complex catalyzed the asymmetric addition of methanol and peroxides to isatin-derived N-Boc-imines to form chiral quaternary N,O-acetals at the C3 position of the resulting oxiindoles in up to 99% yield with 94% ee.