7-(4-methoxypicolinoyl)-7-azabicyclo[4.1.0]heptane | 1414851-44-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 7-(4-methoxypicolinoyl)-7-azabicyclo[4.1.0]heptane
• CAS: 1414851-44-7
• 化学式: C₁₃H₁₆N₂O₂
• 分子量: 232.282
• InChiKey: CKAHKKVXUIUJPX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.86
• 重原子数：
  17.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  42.2
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  亚磷酸二苯酯 、 7-(4-methoxypicolinoyl)-7-azabicyclo[4.1.0]heptane 在 N-picolynoyl-9-amino-9-deoxy-epi-cinchonine 、 diethylzinc 、 sodium carbonate 作用下， 以 甲苯 、 苯 为溶剂， 反应 1.0h， 以91%的产率得到
  参考文献：
  名称：

  Cinchona Alkaloid Amides/Dialkylzinc Catalyzed Enantioselective Desymmetrization of Aziridines with Phosphites

  摘要：

  The first highly enantioselective desymmetrization of aziridines with phosphites has been developed. Excellent yields and enantio-selectivities were observed for the reaction with various aziridines using a new class of readily accessible chiral catalysts derived from 9-amino-9-deoxy-epi-cinchonas alkaloids. In studies probing the reaction mechanism, we observed some complexes for the cinchona alkaloid amide-Zn(II) by ESI-MS analysis

  DOI：

  10.1021/ja309963w
• 作为产物：
  描述：

  4-硝基-2-甲酸吡啶 在 sodium 、 N,N'-羰基二咪唑 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 生成 7-(4-methoxypicolinoyl)-7-azabicyclo[4.1.0]heptane
  参考文献：
  名称：

  Cinchona Alkaloid Amides/Dialkylzinc Catalyzed Enantioselective Desymmetrization of Aziridines with Phosphites

  摘要：

  The first highly enantioselective desymmetrization of aziridines with phosphites has been developed. Excellent yields and enantio-selectivities were observed for the reaction with various aziridines using a new class of readily accessible chiral catalysts derived from 9-amino-9-deoxy-epi-cinchonas alkaloids. In studies probing the reaction mechanism, we observed some complexes for the cinchona alkaloid amide-Zn(II) by ESI-MS analysis

  DOI：

  10.1021/ja309963w

文献信息

• Chiral Magnesium(II) Complex-Catalyzed Enantioselective Desymmetrization of <i>meso</i> -Aziridines with Pyrazoles
  作者：Xiangqiang Li、Jing Guo、Lili Lin、Haipeng Hu、Fenzhen Chang、Xiaohua Liu、Xiaoming Feng

  DOI：10.1002/adsc.201700888

  日期：2017.10.25

  A highly enantioselective catalytic protocol for the desymmetrization of meso-aziridines via ring-opening with pyrazoles is reported using an N,N′-dioxide-Mg(OTf)2 complex as the catalyst. The corresponding trans-α-pyrazole-substituted amines were obtained in good yields and enantioselectivities (up to 99% yield and 94% ee) under mild reaction conditions. Moreover, a remarkably high asymmetric amplification

  为的desymmetrization高度对映选择性催化协议内消旋-aziridines通过开环与吡唑是使用报道N，N- '二氧化物-的Mg（OTf）2配合物作为催化剂。在温和的反应条件下，以良好的收率和对映选择性（高达99％的收率和94％ee的对映选择性）获得了相应的反式-α-吡唑取代的胺。此外，在催化体系中观察到非常高的不对称扩增。
• Chiral magnesium(ii)-catalyzed asymmetric ring-opening of meso-aziridines with primary alcohols
  作者：Jun Li、Yuting Liao、Yulong Zhang、Xiaohua Liu、Lili Lin、Xiaoming Feng

  DOI：10.1039/c4cc02206h

  日期：——

  The asymmetric ring-opening of meso-aziridines with primary alcohols is realized using an N,N′-dioxide–Mg(OTf)2 complex as the catalyst. The desired vicinal trans-β-amino ethers are afforded in good yields and enantioselectivities. Aniline and water could also be used as the nucleophiles for the ring-opening in an identical catalyst system.

  以N,N′-二氧化物–Mg(OTf)2复合物作为催化剂，初级醇对meso-氮杂环丁烷的不对称开环反应得以实现。所需的邻位反式-β-氨基醚以良好的产率和不对称选择性获得。苯胺和水也可以作为在相同催化体系中的核亲电试剂用于开环反应。
• Desymmetrization of aziridine with malononitrile using cinchona alkaloid amide/zinc(<scp>ii</scp>) catalysts
  作者：Noriyuki Shiomi、Mami Kuroda、Shuichi Nakamura

  DOI：10.1039/c6cc09457k

  日期：——

  The catalytic enantioselective desymmetrization of aziridines with malononitrile has been developed. Good yield and enantioselectivity were obtained by using cinchona alkaloid amide/Zn(II) and base catalysts. The obtained product can be...

  已经开发了丙二腈与丙二腈的催化对映选择性脱对称。使用金鸡纳生物碱酰胺/ Zn（II）和碱催化剂可获得良好的收率和对映选择性。获得的产品可以是...