(2S)-2-(methoxymethyl)-N-[(1E,2E)-2-methylbut-2-en-1-ylidene]pyrrolidin-1-amine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (2S)-2-(methoxymethyl)-N-[(1E,2E)-2-methylbut-2-en-1-ylidene]pyrrolidin-1-amine
• 英文别名: (E,E)-N-[(2S)-2-(methoxymethyl)pyrrolidin-1-yl]-2-methylbut-2-en-1-imine
• 化学式: C₁₁H₂₀N₂O
• 分子量: 196.293
• InChiKey: OBBISNLPPUNNCC-ISCHMAKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  24.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S)-2-(methoxymethyl)-N-[(1E,2E)-2-methylbut-2-en-1-ylidene]pyrrolidin-1-amine 、 3-(1,2-丙二烯)-(9ci)-2-噁唑烷酮 在 (乙腈)[(2-联苯)二叔丁基膦]六氟锑酸金(I) 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 1.0h， 以20%的产率得到
  参考文献：
  名称：

  Gold(I)-Catalyzed Intermolecular Cycloaddition of Allenamides with α,β-Unsaturated Hydrazones: Efficient Access to Highly Substituted Cyclobutanes

  摘要：

  alpha,beta-Unsaturated N,N-dialkyl hydrazones undergo a mild [2 + 2] cycloaddition to allenamides when treated with a suitable gold catalyst. The method, which represents the first application of N,N-dialkyl hydrazones in gold catalysis, is compatible with a wide variety of substituents at the alkenyl moiety of the hydrazone component, proceeds with excellent levels of regio- and diastereoselectivity, and provides densely substituted cyclobutanes with good to excellent yields.

  DOI：

  10.1021/ol503121q
• 作为产物：
  描述：

  反式-2-甲基-2-丁烯醛 、 (S)-1-amino-2-(methoxymethyl)pyrrolidine 在 magnesium sulfate 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以65%的产率得到(2S)-2-(methoxymethyl)-N-[(1E,2E)-2-methylbut-2-en-1-ylidene]pyrrolidin-1-amine
  参考文献：
  名称：

  Gold(I)-Catalyzed Intermolecular Cycloaddition of Allenamides with α,β-Unsaturated Hydrazones: Efficient Access to Highly Substituted Cyclobutanes

  摘要：

  alpha,beta-Unsaturated N,N-dialkyl hydrazones undergo a mild [2 + 2] cycloaddition to allenamides when treated with a suitable gold catalyst. The method, which represents the first application of N,N-dialkyl hydrazones in gold catalysis, is compatible with a wide variety of substituents at the alkenyl moiety of the hydrazone component, proceeds with excellent levels of regio- and diastereoselectivity, and provides densely substituted cyclobutanes with good to excellent yields.

  DOI：

  10.1021/ol503121q

文献信息

• Gold(I)-Catalyzed Intermolecular Cycloaddition of Allenamides with α,β-Unsaturated Hydrazones: Efficient Access to Highly Substituted Cyclobutanes
  作者：Paloma Bernal-Albert、Hélio Faustino、Ana Gimeno、Gregorio Asensio、José L. Mascareñas、Fernando López

  DOI：10.1021/ol503121q

  日期：2014.12.5

  alpha,beta-Unsaturated N,N-dialkyl hydrazones undergo a mild [2 + 2] cycloaddition to allenamides when treated with a suitable gold catalyst. The method, which represents the first application of N,N-dialkyl hydrazones in gold catalysis, is compatible with a wide variety of substituents at the alkenyl moiety of the hydrazone component, proceeds with excellent levels of regio- and diastereoselectivity, and provides densely substituted cyclobutanes with good to excellent yields.