N-methyl-N-(2-propen-1-yl)diazoacetamide | 175163-96-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-methyl-N-(2-propen-1-yl)diazoacetamide
• 英文别名: 2-diazo-N-methyl-N-prop-2-enylacetamide
• CAS: 175163-96-9
• 化学式: C₆H₉N₃O
• 分子量: 139.157
• InChiKey: VOHCOCAEPDWMKW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  22.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-methyl-N-(2-propen-1-yl)diazoacetamide 以 氯仿 为溶剂， 反应 2.5h， 生成 3,3α,4,5,6,6α-hexahydro-5-methylpyrrolo<3,4-c>pyrazol-6-one
  参考文献：
  名称：

  Highly Enantioselective Intramolecular Cyclopropanation Reactions of N-Allylic-N-methyldiazoacetamides Catalyzed by Chiral Dirhodium(II) Carboxamidates

  摘要：

  Catalytic diazo decomposition of representative N-allylic-N-methyldiazoacetamides produced the corresponding intramolecular cyclopropanation products in good to excellent yields and with exceptional enantiocontrol. In the simplest case, with N-allyl-N-methyldiazoacetamide, catalysis by dirhodium(II) tetrakis[methyl 2-oxapyrrolidine-5(S)-carboxylate], Rh-2(5(S)-MEPY)(4), achieved the highest yield and enantioselectivity (93% eel. Dirhodium(II) tetrakis[methyl 2-oxo-1-(3-phenylpropanoyl)imidazolidin-4(S)-carboxylate] Rh-2(4S)-MPPIM)(4), was preferred for substituted N-allylic-N-methyldiazoacetamides from which 92-95% ee's were obtained in intramolecular cyclopropanation reactions (88-95% yields), even when the catalyst was employed in only 0.1 mol %, Competition with intramolecular dipolar cycloaddition was minimized with the use of N-methyldiazoacetamides relative to N-tert-butyldiazoacetamides.

  DOI：

  10.1021/jo9519219
• 作为产物：
  描述：

  N-甲基烯丙基胺 、 succinimidyl diazoacetate 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以84%的产率得到N-methyl-N-(2-propen-1-yl)diazoacetamide
  参考文献：
  名称：

  Highly Enantioselective Intramolecular Cyclopropanation Reactions of N-Allylic-N-methyldiazoacetamides Catalyzed by Chiral Dirhodium(II) Carboxamidates

  摘要：

  Catalytic diazo decomposition of representative N-allylic-N-methyldiazoacetamides produced the corresponding intramolecular cyclopropanation products in good to excellent yields and with exceptional enantiocontrol. In the simplest case, with N-allyl-N-methyldiazoacetamide, catalysis by dirhodium(II) tetrakis[methyl 2-oxapyrrolidine-5(S)-carboxylate], Rh-2(5(S)-MEPY)(4), achieved the highest yield and enantioselectivity (93% eel. Dirhodium(II) tetrakis[methyl 2-oxo-1-(3-phenylpropanoyl)imidazolidin-4(S)-carboxylate] Rh-2(4S)-MPPIM)(4), was preferred for substituted N-allylic-N-methyldiazoacetamides from which 92-95% ee's were obtained in intramolecular cyclopropanation reactions (88-95% yields), even when the catalyst was employed in only 0.1 mol %, Competition with intramolecular dipolar cycloaddition was minimized with the use of N-methyldiazoacetamides relative to N-tert-butyldiazoacetamides.

  DOI：

  10.1021/jo9519219

文献信息

• KOAc-Catalyzed One-Pot Three-Component 1,3-Dipolar Cycloaddition of α-Diazo Compounds, Nitrosoarenes, and Alkenes: An Approach to Functionalized Isoxazolidines
  作者：Xing Li、Tao Feng、Dongjun Li、Honghong Chang、Wenchao Gao、Wenlong Wei

  DOI：10.1021/acs.joc.9b00299

  日期：2019.4.5

  A direct, highly efficient KOAc-catalyzed one-pot three-component approach for the preparation of various functionalized isoxazolidines via the 1,3-dipolar cycloaddition reactions of readily accessible diazo compounds, nitrosoarenes, and alkenes has been reported. The cheap and readily available catalyst and starting materials, excellent functional group compatibility, wide substrate scope, high yields

  已经报道了一种直接，高效的KOAc催化的一锅三组分方法，该方法通过易获得的重氮化合物，亚硝基芳烃和烯烃的1,3-偶极环加成反应制备各种官能化的异恶唑烷。廉价且容易获得的催化剂和起始原料，出色的官能团相容性，广泛的底物范围，高收率以及出色的化学选择性，区域选择性和非对映选择性，使该方案成为有吸引力的替代方案。
• Highly Stereoselective Synthesis of Fused Cyclopropane-γ-Lactams via Biocatalytic Iron-Catalyzed Intramolecular Cyclopropanation
  作者：Xinkun Ren、Ajay L. Chandgude、Rudi Fasan

  DOI：10.1021/acscatal.9b05383

  日期：2020.2.7

  We report the development of an iron-based biocatalytic strategy for the asymmetric synthesis of fused cyclopropane-γ-lactams, which are key structural motifs found in synthetic drugs and bioactive natural products. Using a combination of mutational landscape and iterative site-saturation mutagenesis, sperm whale myoglobin was evolved into a biocatalyst capable of promoting the cyclization of a diverse

  我们报告了不对称合成的稠合环丙烷-γ-内酰胺的铁基生物催化策略的发展，这是在合成药物和生物活性天然产物中发现的关键结构图案。结合使用突变景观和迭代位点饱和诱变技术，抹香鲸肌红蛋白已发展成为一种生物催化剂，能够以高收率和高对映选择性（高达99种）促进各种烯丙基重氮乙酰胺底物环化成相应的双环内酰胺。 ％ee）。这些生物催化转化可在整个细胞中进行，并可用于使手性环丙烷-γ-内酰胺以及β-环丙胺和环丙烷稠合的吡咯烷酮高效（化学）酶促构建，
• Highly Enantioselective Intramolecular Cyclopropanation Reactions of <i>N</i>-Allylic-<i>N</i>-methyldiazoacetamides Catalyzed by Chiral Dirhodium(II) Carboxamidates
  作者：Michael P. Doyle、Alexey V. Kalinin

  DOI：10.1021/jo9519219

  日期：1996.1.1

  Catalytic diazo decomposition of representative N-allylic-N-methyldiazoacetamides produced the corresponding intramolecular cyclopropanation products in good to excellent yields and with exceptional enantiocontrol. In the simplest case, with N-allyl-N-methyldiazoacetamide, catalysis by dirhodium(II) tetrakis[methyl 2-oxapyrrolidine-5(S)-carboxylate], Rh-2(5(S)-MEPY)(4), achieved the highest yield and enantioselectivity (93% eel. Dirhodium(II) tetrakis[methyl 2-oxo-1-(3-phenylpropanoyl)imidazolidin-4(S)-carboxylate] Rh-2(4S)-MPPIM)(4), was preferred for substituted N-allylic-N-methyldiazoacetamides from which 92-95% ee's were obtained in intramolecular cyclopropanation reactions (88-95% yields), even when the catalyst was employed in only 0.1 mol %, Competition with intramolecular dipolar cycloaddition was minimized with the use of N-methyldiazoacetamides relative to N-tert-butyldiazoacetamides.