(E)-(-)-(1'R,2'R)-N-methyl-N-(2'-phenyl-2'-hydroxy-1'-methylethyl)but-2-enamide | 1061728-06-0

• 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: (E)-(-)-(1'R,2'R)-N-methyl-N-(2'-phenyl-2'-hydroxy-1'-methylethyl)but-2-enamide
• 英文别名: (E)-N-[(1R,2R)-1-hydroxy-1-phenylpropan-2-yl]-N-methylbut-2-enamide
• CAS: 1061728-06-0
• 化学式: C₁₄H₁₉NO₂
• 分子量: 233.31
• InChiKey: CCCWVBDIDOTWGV-MUPFWISGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  (E)-(-)-(1'R,2'R)-N-methyl-N-(2'-phenyl-2'-hydroxy-1'-methylethyl)but-2-enamide 、 正戊基溴化镁 在 copper(I) bromide dimethylsulfide complex 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 6.0h， 以93%的产率得到(-)-(1'R,2'R)-N-methyl-N-(2'-phenyl-2'-hydroxy-1'-methylethyl)-3-methyloctanamide
  参考文献：
  名称：

  Stereoselective 1,4-addition of Grignard reagents to α,β-enamides using a combined chiral auxiliary-catalyst approach

  摘要：

  A catalyst composed of (R,R)-MeDuphos and CuBr center dot SMe(2) catalyzes the addition of RMgBr (R = Et, C(5)H(11), Ph) to simple enamides (E)-Me(2)NCOCH = CHR(1) (R(1) = Me, C(5)H(11)) in acceptable yields (50-78%), but with poor to modest enantioselectivities (0-74% ee). By changing the enamide acceptor to the (E)-(Aux)N-COCH = CHMe [Aux = from commercial pseudoephedrine, (R,R)-NMeCHMeCHPhOH] a stereochemically enhanced regime Could be attained. Structurally diverse RMgBr (R = C(5)H(11), vinyl, allyl, Ph) underwent 1,4-additions in 57-89% de and 88-93% yield. In one case, the resulting enolate could be trapped with allyl bromide. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.06.017
• 作为产物：
  描述：

  2-丁烯酰氯 、 左旋伪麻黄碱 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 以92%的产率得到(E)-(-)-(1'R,2'R)-N-methyl-N-(2'-phenyl-2'-hydroxy-1'-methylethyl)but-2-enamide
  参考文献：
  名称：

  Stereoselective 1,4-addition of Grignard reagents to α,β-enamides using a combined chiral auxiliary-catalyst approach

  摘要：

  A catalyst composed of (R,R)-MeDuphos and CuBr center dot SMe(2) catalyzes the addition of RMgBr (R = Et, C(5)H(11), Ph) to simple enamides (E)-Me(2)NCOCH = CHR(1) (R(1) = Me, C(5)H(11)) in acceptable yields (50-78%), but with poor to modest enantioselectivities (0-74% ee). By changing the enamide acceptor to the (E)-(Aux)N-COCH = CHMe [Aux = from commercial pseudoephedrine, (R,R)-NMeCHMeCHPhOH] a stereochemically enhanced regime Could be attained. Structurally diverse RMgBr (R = C(5)H(11), vinyl, allyl, Ph) underwent 1,4-additions in 57-89% de and 88-93% yield. In one case, the resulting enolate could be trapped with allyl bromide. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.06.017

文献信息

• Stereoselective 1,4-addition of Grignard reagents to α,β-enamides using a combined chiral auxiliary-catalyst approach
  作者：Kallolmay Biswas、Simon Woodward

  DOI：10.1016/j.tetasy.2008.06.017

  日期：2008.7

  A catalyst composed of (R,R)-MeDuphos and CuBr center dot SMe(2) catalyzes the addition of RMgBr (R = Et, C(5)H(11), Ph) to simple enamides (E)-Me(2)NCOCH = CHR(1) (R(1) = Me, C(5)H(11)) in acceptable yields (50-78%), but with poor to modest enantioselectivities (0-74% ee). By changing the enamide acceptor to the (E)-(Aux)N-COCH = CHMe [Aux = from commercial pseudoephedrine, (R,R)-NMeCHMeCHPhOH] a stereochemically enhanced regime Could be attained. Structurally diverse RMgBr (R = C(5)H(11), vinyl, allyl, Ph) underwent 1,4-additions in 57-89% de and 88-93% yield. In one case, the resulting enolate could be trapped with allyl bromide. (C) 2008 Elsevier Ltd. All rights reserved.