甲基[(E)-(3-氟苯基)亚甲基]氨基甲酸酯 | 917752-19-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 甲基[(E)-(3-氟苯基)亚甲基]氨基甲酸酯
• 英文名称: (3-Fluoro-benzylidene)-carbamic acid methyl ester
• 英文别名: Methyl [(3-fluorophenyl)methylidene]carbamate；methyl N-[(3-fluorophenyl)methylidene]carbamate
• CAS: 917752-19-3
• 化学式: C₉H₈FNO₂
• 分子量: 181.166
• InChiKey: OCOJHVHJLQEMFK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  38.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  甲基[(E)-(3-氟苯基)亚甲基]氨基甲酸酯 、 丙二酸二甲酯 在 F-UiO-66-(COOH)₂ 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以99%的产率得到
  参考文献：
  名称：

  Synthesis of a flower-like Zr-based metal–organic framework and study of its catalytic performance in the Mannich reaction

  摘要：

  UiO-66-(COOH)₂ 具有花状形态，首次合成并研究了其异质Brønsted酸催化活性。

  DOI：

  10.1039/c4ra15257c

文献信息

• The synthesis of metal-organic framework Al-MIL-53-derived Brønsted acid catalyst and its application in the Mannich reaction
  作者：Zongcheng Miao、Chao Qi、Liangshi Wang、Allison M. Wensley、Yi Luan

  DOI：10.1002/aoc.3569

  日期：2017.2

  A metal–organic framework Al‐MIL‐53‐NH2‐derived Brønsted acid catalyst (Al‐MIL‐53‐RSO3H) has been synthesized employing a post‐synthetic modification strategy under mild conditions. The Al‐MIL‐53‐RSO3H catalyst was successfully utilized in the nitro‐Mannich reaction taking advantage of its strong Brønsted acidity. Good to excellent yields of Mannich adducts were achieved for a variety of acylimine

  金属-有机骨架Al-MIL-53-NH 2衍生的布朗斯台德酸催化剂（Al-MIL-53-RSO 3 H）在温和条件下采用合成后修饰策略合成。Al-MIL-53-RSO 3 H催化剂凭借其强大的布朗斯台德酸度成功地用于硝基曼尼希反应中。在存在0.1 mol％Al‐MIL‐53‐RSO 3 H的情况下，对于各种酰基亚胺底物，曼尼希加合物的收率达到了良好或优异的水平。此外，Al‐MIL‐53‐RSO 3 H催化剂可循环使用五次而不降低曼尼希加合物的收率和选择性。
• Multicomponent Mannich Reactions with Boron Enolates Derived from Diazo Esters and 9-BBN
  作者：Yi Luan、Scott E. Schaus

  DOI：10.1021/ol200766t

  日期：2011.5.6

  3-component Mannich condensation reaction. Catalyzed by Cu(II) salts, the reaction affords the corresponding isocyanate Mannich product: one that can be easily trapped in situ by other nucleophiles. The Mannich condensation corresponds to an α,α-disubstituted enolate addition to imines. The reaction was rendered asymmetric by using the (−)-phenylmenthol ester in good yield and selectivities.

  重氮酯、芳基硼烷和氨基甲酰亚胺会发生三组分曼尼希缩合反应。在 Cu(II) 盐的催化下，该反应产生相应的异氰酸酯曼尼希产物：一种很容易被其他亲核试剂原位捕获的产物。曼尼希缩合对应于亚胺上的α,α-二取代烯醇化物加成。通过使用 (-)-苯基薄荷醇酯使反应不对称，具有良好的产率和选择性。
• Catalytic Asymmetric Imine Cross-Coupling Reaction
  作者：Xiang-Lei Han、Bin Hu、Chao Fei、Zhe Li、Yang Yu、Cheng Cheng、Bruce Foxman、Jisheng Luo、Li Deng

  DOI：10.1021/jacs.3c00051

  日期：2023.3.1

  unprecedented catalytic asymmetric cross-coupling reaction that tolerates a variety of ketimines and aldimines as nucleophiles and electrophiles, respectively. The realization of this reaction resulted from the development of a new chiral ammonium catalyst, which was guided by insights from studies of catalyst–substrate interactions. With a 0.5 mol % loading of an organocatalyst, this reaction proceeded

  亚胺的催化不对称交叉偶联构成了一种特别理想的方法，用于直接从容易获得的非手性前体合成手性邻位二胺。这种方法的潜力在于可以利用各种亚胺作为反应伙伴。然而，实现两种不同亚胺的高度立体选择性交叉偶联被证明是一项艰巨的挑战。在此，我们报告了一种前所未有的催化不对称交叉偶联反应，该反应可分别耐受各种酮亚胺和醛亚胺作为亲核试剂和亲电子试剂。该反应的实现源于新型手性铵催化剂的开发，该催化剂受到催化剂-底物相互作用研究的启发。在有机催化剂负载量为 0.5 mol % 的情况下，该反应以高度非对映和对映选择性的方式进行，以提供多种手性邻位二胺作为几乎单一的立体异构体。该催化反应为手性邻位二胺的不对称合成建立了新途径。
• Diastereoselective Three-Component Synthesis of β-Amino Carbonyl Compounds Using Diazo Compounds, Boranes, and Acyl Imines under Catalyst-Free Conditions
  作者：Yi Luan、Jie Yu、Xiaowei Zhang、Scott E. Schaus、Ge Wang

  DOI：10.1021/jo5003505

  日期：2014.5.16

  Diazo compounds, boranes, and acyl imines undergo a three-component Mannich condensation reaction under catalyst-free conditions to give the anti beta-amino carbonyl compounds in high diastereoselectivity. The reaction tolerates a variety of functional groups, and an asymmetric variant was achieved using the (-)-phenylmenthol as chiral auxiliary in good yield and selectivity. These beta-amino carbonyl compounds are valuable intermediates, which can be transformed to many potential bioactive molecules.
• Synthesis of a flower-like Zr-based metal–organic framework and study of its catalytic performance in the Mannich reaction
  作者：Yi Luan、Yue Qi、Zhaokui Jin、Xiong Peng、Hongyi Gao、Ge Wang

  DOI：10.1039/c4ra15257c

  日期：——

  UiO-66-(COOH)₂ with flower-like morphology was synthesized for the first time and its heterogeneous Brønsted acidic catalytic activities have been studied.

  UiO-66-(COOH)₂ 具有花状形态，首次合成并研究了其异质Brønsted酸催化活性。