N-(4-bromophenyl)-1-(4-chlorophenyl)methanimine oxide | 1344025-72-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(4-bromophenyl)-1-(4-chlorophenyl)methanimine oxide
• CAS: 1344025-72-4
• 化学式: C₁₃H₉BrClNO
• 分子量: 310.578
• InChiKey: WTGZIMILBYEYAR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  28.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-(4-bromophenyl)-1-(4-chlorophenyl)methanimine oxide 在 盐酸 、 rhodium(II) acetate dimer 、 copper(I) hexafluorophosphate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 5.5h， 生成 methyl 1-(4-bromophenyl)-5-(4-chlorophenyl)-3-hydroxy-1H-pyrrole-2-carboxylate
  参考文献：
  名称：

  Multifunctionalized 3-Hydroxypyrroles in a Three-Step, One-Pot Cascade Process from Methyl 3-TBSO-2-diazo-3-butenoate and Nitrones

  摘要：

  The synthesis of N-aryl-2-carboxyl-3-hydroxy-5-arylpyrroles has been achieved in high yield by the combination of a TBSO-substituted vinyldiazoacetate and nitrones in a one-pot cascade process involving copper-catalyzed Mannich addition, dirhodium-catalyzed dinitrogen extrusion and N-OTBS insertion, and acid-promoted aromatization (elimination).

  DOI：

  10.1021/ol2026125

文献信息

• Enantioselective Oxidative Multi-Functionalization of Terminal Alkynes with Nitrones and Alcohols for Expeditious Assembly of Chiral α-Alkoxy-β-amino-ketones
  作者：Su Zhou、Yinwu Li、Xiangrong Liu、Wenhao Hu、Zhuofeng Ke、Xinfang Xu

  DOI：10.1021/jacs.1c06178

  日期：2021.9.15

  functionalization of alkynes has emerged as an effective method in synthetic chemistry in recent decades. However, enantioselective transformations via metal carbene intermediates are quite rare due to the lack of robust chiral catalysts, especially in the intermolecular versions. Herein, we report the first asymmetric three-component reaction of commercially available alkynes with nitrones and alcohols, which affords

  近几十年来，炔烃的催化氧化功能化已成为合成化学中的一种有效方法。然而，由于缺乏强大的手性催化剂，特别是在分子间版本中，通过金属卡宾中间体进行的对映选择性转化非常罕见。在此，我们报告了第一个市售炔烃与硝酮和醇的不对称三组分反应，该反应通过非手性金配合物和手性金配合物的联合催化，以良好的收率和高至优异的对映选择性得到 α-烷氧基-β-氨基酮。螺磷酸（CPA）。从机制上讲，这种原子经济反应涉及催化炔氧化/叶立德形成/曼尼希型加成序列，该序列使用硝酮作为氧化剂，离开片段亚胺作为亲电子试剂，
• Highly Regio- and Stereoselective Dirhodium Vinylcarbene Induced Nitrone Cycloaddition with Subsequent Cascade Carbenoid Aromatic Cycloaddition/NO Cleavage and Rearrangement
  作者：Xiaochen Wang、Quentin M. Abrahams、Peter Y. Zavalij、Michael P. Doyle

  DOI：10.1002/anie.201201917

  日期：2012.6.11

  An abnormal cascade process provides a selective method for the preparation of tricyclic heterocycles. The cascade involves a metal carbene induced regioselective [3+2] cycloaddition, a Buchner reaction, and a [1,7]‐oxygen migration, which occurs with NO cleavage (see scheme). The products are formed with remarkable specificity.

  异常的级联过程提供了制备三环杂环的选择性方法。级联涉及诱导区域选择性[3 + 2]环加成的金属卡宾，布氏反应，和[1,7] -氧迁移，这与N-发生 ø裂解（参见方案）。产物具有明显的特异性。
• An asymmetric oxidative cyclization/Mannich-type addition cascade reaction for direct access to chiral pyrrolidin-3-ones
  作者：Su Zhou、Xiongda Xie、Xinxin Xu、Shanliang Dong、Wenhao Hu、Xinfang Xu

  DOI：10.1039/d1cc04830a

  日期：——

  gold and chiral phosphoric acid cooperatively catalyzed enantioselective oxidative cyclization/Mannich-type addition reaction of homopropargyl amides with nitrones has been developed, which provides chiral pyrrolidin-3-ones in high yields with excellent enantioselectivities under mild conditions. This reaction employed stable and readily available alkynes as non-diazo carbene precursors, which provides

  已经开发出一种高效的金和手性磷酸协同催化高炔丙基酰胺与硝酮的对映选择性氧化环化/曼尼希型加成反应，在温和的条件下以高产率提供具有优异对映选择性的手性吡咯烷-3-酮。该反应使用稳定且容易获得的炔烃作为非重氮卡宾前体，提供了一种具有高成键效率的 100% 原子经济方法。
• A donor–acceptor cyclopropene as a dipole source for a silver(i) catalyzed asymmetric catalytic [3+3]-cycloaddition with nitrones
  作者：Xinfang Xu、Peter J. Zavalij、Michael P. Doyle

  DOI：10.1039/c3cc46415f

  日期：——

  Silver(I)-catalyzed asymmetric formal [3+3]-cycloaddition of nitrones with a donor-acceptor cyclopropene, formed in situ from dirhodium acetate-catalyzed dinitrogen extrusion/intramolecular cyclization of enoldiazoacetates, effectively generates 3,6-dihydro-1,2-oxazine derivatives in high yield and with exceptional stereocontrol.

  银（I）催化的硝酮与供体-受体环丙烯的不对称正构[3 + 3]环加成反应，是由乙酸乙二胺酯催化的二氮挤出/烯丙乙酸酯的分子内环化反应原位形成的，可有效生成3,6-dihydro-1， 2-恶嗪衍生物，收率高，立体控制效果好。