N-((1R,2S)-2-hydroxy-1-methyl-2-phenylethyl)-N-methyl-acrylamide | 623157-95-9

• 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-((1R,2S)-2-hydroxy-1-methyl-2-phenylethyl)-N-methyl-acrylamide
• 英文别名: N-[(1S,2R)-1-hydroxy-1-phenylpropan-2-yl]-N-methylprop-2-enamide
• CAS: 623157-95-9
• 化学式: C₁₃H₁₇NO₂
• 分子量: 219.283
• InChiKey: VSGNSQQWOOSGJC-ZWNOBZJWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-((1R,2S)-2-hydroxy-1-methyl-2-phenylethyl)-N-methyl-acrylamide 在 silver(I) acetate 、 magnesium 、 三乙胺 作用下， 以 乙醚 、 甲苯 为溶剂， 反应 27.0h， 生成
  参考文献：
  名称：

  Silver acetate-catalysed asymmetric 1,3-dipolar cycloadditions of imines and chiral acrylamides

  摘要：

  N-Metallated azomethine ylides were generated by the reaction of arylidene glycine imines with AgOAc and triethylamine. These azomethine ylides undergo cycloaddition to chiral acrylamides with excellent diastereoselectivity. The configuration of two of the cycloadducts was confirmed by X-ray crystallography. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.02.009
• 作为产物：
  描述：

  盐酸右旋麻黄碱 、 Methoxycarbonyl prop-2-enoate 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 N-((1R,2S)-2-hydroxy-1-methyl-2-phenylethyl)-N-methyl-acrylamide
  参考文献：
  名称：

  Silver acetate-catalysed asymmetric 1,3-dipolar cycloadditions of imines and chiral acrylamides

  摘要：

  N-Metallated azomethine ylides were generated by the reaction of arylidene glycine imines with AgOAc and triethylamine. These azomethine ylides undergo cycloaddition to chiral acrylamides with excellent diastereoselectivity. The configuration of two of the cycloadducts was confirmed by X-ray crystallography. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.02.009

文献信息

• Silver Acetate Catalysed Asymmetric1,3-Dipolar Cycloadditions of Imines and Chiral Acrylamides
  作者：Miklós Nyerges、David Bendell、Andrea Arany、David E. Hibbs、Simon J. Coles、Michael B. Hursthouse、Paul W. Groundwater、Otto Meth-Cohn

  DOI：10.1055/s-2003-39325

  日期：——

  N-Metallated azomethine ylides 5 were generated by the reaction of arylidene glycine imines 1 with AgOAc and triethyl­amine. These azomethine ylides undergo cycloaddition to chiral acrylamides 2 with excellent diastereoselectivity. The configuration of two of the cycloadducts (3a 1 and 3c 1 ) has been confirmed by X-ray crystallography.

  N-金属化的偶氮甲碱叶立德5是通过芳亚甲基甘氨酸亚胺1与AgOAc和三乙胺反应生成的。这些偶氮甲碱叶立德以优异的非对映选择性与手性丙烯酰胺2进行环加成反应。其中两个环加成产物（3a¹和3c¹）的构型已通过X射线晶体学得到确认。