(Z)-methyl 3-acetamido-5-methyl-2-hexenoate | 136744-86-0

• 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: (Z)-methyl 3-acetamido-5-methyl-2-hexenoate
• 英文别名: (E)-methyl 5-methyl-3-acetamido-2-hexenoate；methyl (Z)-3-acetamido-5-methylhex-2-enoate
• CAS: 136744-86-0
• 化学式: C₁₀H₁₇NO₃
• 分子量: 199.25
• InChiKey: FEMZFWCPYWJHSS-TWGQIWQCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (Z)-methyl 3-acetamido-5-methyl-2-hexenoate 在 palladium on activated charcoal lithium aluminium tetrahydride 、 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 28.5h， 生成 3-ethylamino-5-methyl-1-hexanol
  参考文献：
  名称：

  Enantioselective synthesis of β-amino acids based on BINAP—ruthenium(II) catalyzed hydrogenation

  摘要：

  BINAP-Ru(II) catalyzed hydrogenation of beta-substituted (E)-beta-(acylamino)acrylic acids allows efficient enantioselective synthesis of beta-amino acids. The Z double bond isomers which possess an intramolecular hydrogen bond between amide and ester groups are more reactive but are hydrogenated with poor enantioselectivity. BINAP-Rh(I) complexes afford only moderate stereoselectivity with the opposite sense of enantioselection.

  DOI：

  10.1016/s0957-4166(00)86107-8
• 作为产物：
  描述：

  5-甲基-3-氧代己酸甲酯 在 吡啶 、 ammonium acetate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 96.0h， 生成 (Z)-methyl 3-acetamido-5-methyl-2-hexenoate
  参考文献：
  名称：

  Enantioselective synthesis of β-amino acids based on BINAP—ruthenium(II) catalyzed hydrogenation

  摘要：

  BINAP-Ru(II) catalyzed hydrogenation of beta-substituted (E)-beta-(acylamino)acrylic acids allows efficient enantioselective synthesis of beta-amino acids. The Z double bond isomers which possess an intramolecular hydrogen bond between amide and ester groups are more reactive but are hydrogenated with poor enantioselectivity. BINAP-Rh(I) complexes afford only moderate stereoselectivity with the opposite sense of enantioselection.

  DOI：

  10.1016/s0957-4166(00)86107-8

文献信息

• Highly Efficient Asymmetric Synthesis of β-Amino Acid Derivatives via Rhodium-Catalyzed Hydrogenation of β-(Acylamino)acrylates
  作者：Guoxin Zhu、Zhaogen Chen、Xumu Zhang

  DOI：10.1021/jo990565h

  日期：1999.9.1
• Enantioselective synthesis of β-amino acids based on BINAP—ruthenium(II) catalyzed hydrogenation
  作者：William D. Lubell、Masato Kitamura、Ryoji Noyori

  DOI：10.1016/s0957-4166(00)86107-8

  日期：1991.1

  BINAP-Ru(II) catalyzed hydrogenation of beta-substituted (E)-beta-(acylamino)acrylic acids allows efficient enantioselective synthesis of beta-amino acids. The Z double bond isomers which possess an intramolecular hydrogen bond between amide and ester groups are more reactive but are hydrogenated with poor enantioselectivity. BINAP-Rh(I) complexes afford only moderate stereoselectivity with the opposite sense of enantioselection.