2-hydroxy-N-methoxy-N-methyl-3-phenylpropanamide | 188548-67-6

• 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: 2-hydroxy-N-methoxy-N-methyl-3-phenylpropanamide
• 英文别名: (R)-2-hydroxy-N-methoxy-N-methyl-3-phenylpropanamide；(2R)-2-hydroxy-N-methoxy-N-methyl-3-phenylpropanamide
• CAS: 188548-67-6
• 化学式: C₁₁H₁₅NO₃
• 分子量: 209.245
• InChiKey: LVFNIOHDWLBQMU-SNVBAGLBSA-N

物化性质

• 沸点：
  315.3±52.0 °C(predicted)
• 密度：
  1.159±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  15
• 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：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-hydroxy-N-methoxy-N-methyl-3-phenylpropanamide 在 吡啶 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 11.5h， 生成 5-[(S)-2-Imidazol-1-yl-1,3-diphenyl-prop-(E)-ylideneaminooxy]-pentanoic acid ethyl ester
  参考文献：
  名称：

  Nucleophilic substitution on α-mesyloxy-O-alkyloximes—I. Enantiospecific synthesis of 2-(imidazol-1-yl)-1,3-diphenylpropan-1-one O-alkyloximes

  摘要：

  An enantiospecific synthesis of (S)- and (R)-(E)-5-[1,3-diphenyl-2-(imidazol-l-yl)propylidene] aminooxypentanoic acids 1 using homochiral phenylalanines as starting material is described. Chiral alpha-hydroxyketones 9 were obtained from alpha-hydroxyacids 7 by Weinreb's ketone synthesis. Imidazole introduction by nucleophilic substitution on mesylate 10 led to 2-(imidazol-1-yl)propan-1-one derivative 3, key intermediate in the synthesis of 1. However, the low configurational stability displayed by compound 3 compromised its use in an enantiospecific synthesis. Homochiral compounds 1 were then obtained by a nucleophilic substitution on alpha-mesyloxy-O-alkyloxymes 14 which were in turn obtained from 9. This nucleophilic substitution on alpha-mesyloxy-O-alkyloxymes was not previously reported either on homochiral compounds or on racemic derivatives. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(96)00505-8
• 作为产物：
  描述：

  D-3-苯乳酸 在 硫酸 、 异丙基氯化镁 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 4.5h， 生成 2-hydroxy-N-methoxy-N-methyl-3-phenylpropanamide
  参考文献：
  名称：

  通过有机催化共轭添加α-氰基乙酸酯到甲基丙烯酸甲酯上的全碳叔/季不相邻立体中心的不对称组装

  摘要：

  基于布朗斯台德碱催化的迈克尔加成/α-质子化序列，涉及α-氰基乙酸酯和2,4-二甲基-4-基羟基戊烯-3-一作为新的甲基丙烯酸酯等同物。

  DOI：

  10.1002/chem.201603082

文献信息

• Pd-Catalyzed Decarboxylative Cycloaddition for the Synthesis of Highly Substituted δ-Lactones and Lactams
  作者：Linlin Shi、Yingdong He、Jianxian Gong、Zhen Yang

  DOI：10.1021/acs.organomet.0c00646

  日期：2021.2.8

  An efficient palladium-catalyzed decarboxylative cycloaddition process of vinyl cyclic carbonates and vinyloxazolidinones for the synthesis of highly substituted δ-lactone and δ-lactam derivatives was developed. This protocol exhibits several unique characteristics, including broad substrate scope, good functional group tolerance, and operational convenience, which enables a regioselective access to

  开发了一种高效的钯催化的乙烯基碳酸酯和乙烯基恶唑烷酮的脱羧环加成法，用于合成高度取代的δ-内酯和δ-内酰胺衍生物。该方案具有几个独特的特征，包括广泛的底物范围，良好的官能团耐受性和操作便利性，从而可以以中等至良好的产率选择性地进入各种内酯和内酰胺支架。氧化还原中性催化系统通过原位产生环状四取代的双键官能团促进取代的支架的形成。
• Ru-catalyzed highly enantioselective hydrogenation of α-keto Weinreb amides
  作者：MengMeng Zhao、WanFang Li、Xin Ma、WeiZheng Fan、XiaoMing Tao、XiaoMing Li、XiaoMin Xie、ZhaoGuo Zhang

  DOI：10.1007/s11426-012-4790-8

  日期：2013.3

  Asymmetric hydrogenation of α-keto Weinreb amides has been realized with [Ru((S)-Sunphos)(benzene)Cl]Cl as the catalyst and CeCl3·7H2O as the additive. A series of enantiopure α-hydroxy Weinreb amides (up to 97% ee) have been obtained. Catalytic amount of CeCl3·7H2O is essential for the high reactivity and enantioselectivity and the ratio of CeCl3·7H2O to [Ru((S)-Sunphos)(benzene)Cl]Cl plays an important role in the hydrogenation reaction.

  α-酮维纳布酰胺的不对称氢化已利用[Ru((S)-Sunphos)(benzene)Cl]Cl作为催化剂，CeCl3·7H2O作为添加剂实现。获得了一系列对映体纯的α-羟基维纳布酰胺（最高可达97%的对映体过量）。催化量的 ·7H2O对于高反应性和对映选择性至关重要， ·7H2O与[Ru((S)-Sunphos)(benzene)Cl]Cl的比例在氢化反应中也起着重要作用。
• Nucleophilic substitution on α-mesyloxy-O-alkyloximes—II. Enantiospecific synthesis of 2-(imidazol-1-yl)-1-cyclohexyl-3-phenylpropan-1-one O-alkyloximes
  作者：Antonio Giordani、Alberto Carera、Vittorio Pinciroli、Paolo Cozzi

  DOI：10.1016/s0957-4166(96)00506-x

  日期：1997.1

  An enantiospecific synthesis of (S)- and (R)-(E)-5-[1-cyclohexyl-3-phenyl-2(imidazol-1-yl)propylidene]aminooxypentanoic acids 2 using homochiral phenylalanines as starting material is described. Protected alpha-hydroxy-N,O-dimethylamides 4, obtained from alpha-hydroxyacids 3 were coupled with 1-cyclohexenyllithium to afford alpha,beta-enones 5, which were in turn converted to alpha-hydroxyketones 6. Configurational liability of compound 11, prompted us to attempt imidazole introduction on the alpha-hydroxy-O-alkyloxymes 12 which proved to be configurationally more stable. Thus nucleophilic substitution on alpha-mesyloxy-O-alkyloxymes 14 led, after ester removal, to homochiral compounds 2. The use of hydrogenolysis for 14b deblocking provided 2a with 97% ee. Considerations on the stereochemical outcome of this hitherto undescribed nucleophilic substitution on alpha-mesyloxy-O-alkyloxymes are reported. (C) 1997 Elsevier Science Ltd.