(R)-N,N-dimethyl-3-methylpentanamide | 1051483-41-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (R)-N,N-dimethyl-3-methylpentanamide
• 英文别名: (3R)-N,N,3-trimethylpentanamide
• CAS: 1051483-41-0
• 化学式: C₈H₁₇NO
• 分子量: 143.229
• InChiKey: GRQKXQAOEDQPKW-SSDOTTSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  (E)-N,N-dimethylcrotonamide 、 乙基溴化镁 在 copper(I) bromide dimethylsulfide complex 作用下， 以 乙醚 为溶剂， 反应 2.0h， 生成 (R)-N,N-dimethyl-3-methylpentanamide 、 (3S)-N,N,3-三甲基戊烷酰胺
  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