(E)-methyl 5-methyl-3-acetamido-2-hexenoate | 136744-87-1

• 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: (E)-methyl 5-methyl-3-acetamido-2-hexenoate
• 英文别名: (E)-methyl 3-acetamido-5-methyl-2-hexenoate；methyl (E)-3-acetamido-5-methylhex-2-enoate
• CAS: 136744-87-1
• 化学式: C₁₀H₁₇NO₃
• 分子量: 199.25
• InChiKey: FEMZFWCPYWJHSS-RMKNXTFCSA-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：

  (E)-methyl 5-methyl-3-acetamido-2-hexenoate 在 盐酸 、 ditrifluoroacetato[(S)-(−)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl]ruthenium(II) 、 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 25.0 ℃ 、405.3 kPa 条件下， 反应 37.0h， 生成 L-β-高亮氨酸
  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 (E)-methyl 5-methyl-3-acetamido-2-hexenoate
  参考文献：
  名称：

  Highly Efficient Asymmetric Synthesis of β-Amino Acid Derivatives via Rhodium-Catalyzed Hydrogenation of β-(Acylamino)acrylates

  摘要：

  DOI：

  10.1021/jo990565h

文献信息

• Six-membered bis(azaphosphorinane), readily available ligand for highly enantioselective asymmetric hydrogenations
  作者：Yongjun Yan、Xumu Zhang

  DOI：10.1016/j.tetlet.2006.01.003

  日期：2006.3

  A new six-membered bis(azaphosphorinane) ligand has been readily prepared starting from an inexpensive chiral epoxide; excellent enantioselectivities (up to over 99% ee) have been achieved in the Rh-catalyzed asymmetric hydrogenations of β-dehydroamino acid derivatives and α-arylenamides.

  一种新的六元双（氮杂磷杂环丁烷）配体已经很容易地从廉价的手性环氧化物开始制备。在Rh催化的β-脱氢氨基酸衍生物和α-芳基酰胺的不对称加氢反应中，实现了极好的对映选择性（高达99％ee以上）。
• A Flexible Approach to Different Families of Bidentate P,P Ligands as Highly Efficient Ligands for Asymmetric Catalysis
  作者：Ulrich Berens、Ulli Englert、Stefan Geyser、Jan Runsink、Albrecht Salzer

  DOI：10.1002/ejoc.200500937

  日期：2006.5

  bidentate phospholane and phosphinite ligands based on a benzothiophene scaffold. The ligand functions in the bidentate ligands can be introduced independently and consecutively. A bis-phospolane ligand as well as its rhodium complex have been characterized by crystal-structure determinations. The bis-phospholane ligands were tested in the catalysed asymmetric homogeneous hydrogenation of dehydroamino

  一种新颖且通用的方法导致基于苯并噻吩支架合成各种类型的单齿和双齿磷杂环戊烷和次膦酸盐配体。双齿配体中的配体功能可以独立和连续引入。双膦烷配体及其铑配合物已通过晶体结构测定进行表征。双磷杂环戊烷配体在脱氢氨基酸衍生物、烯酰胺和衣康酸酯的催化不对称均相氢化中进行了测试，得到了高达 98.7% 的 ee 值。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)
• Highly Efficient Synthesis of Chiral β-Amino Acid Derivatives via Asymmetric Hydrogenation
  作者：Wenjun Tang、Xumu Zhang

  DOI：10.1021/ol026935x

  日期：2002.11.1

  The Rh-TangPhos complex is an efficient hydrogenation catalyst for making chiral beta-amino acid derivatives. With the Rh-TangPhos system, high enantioselectivities (up to 99.6%) and turnover numbers have been obtained in the hydrogenation of E/Z isomeric mixtures of both beta-alkyl and beta-aryl beta-(acylamino)acrylates. [reaction: see text]

  Rh-TangPhos配合物是一种高效的氢化催化剂，可用于制备手性β-氨基酸衍生物。使用Rh-TangPhos系统，在β-烷基和β-芳基β-（酰基氨基）丙烯酸酯的E / Z异构体混合物的氢化中，获得了高对映选择性（高达99.6％）和周转率。[反应：看文字]