methyl 5-methyl-3-acetamidohexanoate | 136781-36-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl 5-methyl-3-acetamidohexanoate
• 英文别名: methyl 3-acetamido-5-methylhexanoate
• CAS: 136781-36-7
• 化学式: C₁₀H₁₉NO₃
• 分子量: 201.266
• InChiKey: GEFIJIYCRPRTIV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 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：

  methyl 5-methyl-3-acetamidohexanoate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以94%的产率得到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：

  异戊酰氯 在 palladium on activated charcoal 吡啶 、 ammonium acetate 、 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 142.0h， 生成 methyl 5-methyl-3-acetamidohexanoate
  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

• A cheap metal for a challenging task: nickel-catalyzed highly diastereo- and enantioselective hydrogenation of tetrasubstituted fluorinated enamides
  作者：Yu-Qing Guan、Zhengyu Han、Xiuxiu Li、Cai You、Xuefeng Tan、Hui Lv、Xumu Zhang

  DOI：10.1039/c8sc04002h

  日期：——

  acidity of the solvent plays a critical role in the control of diastereoselectivity by trapping the adduct of nickel hydride to CC bonds via protonolysis, giving the hydrogenation product with stereospecific syn-selectivity. This protocol provides efficient access to chiral α-fluoro-β-amino esters which have important potential applications in organic synthesis and medicinal chemistry.

  已经实现了具有挑战性的四取代氟化烯酰胺的镍催化不对称氢化，以高产率提供手性 α-氟-β-氨基酯，具有出色的非对映和对映选择性（高达 98% 产率，>99 : 1 dr，高达 >99 %ee)。进行了氘标记实验和对照实验以探究其机理，结果表明，溶剂的酸度通过质子分解捕获氢化镍与 C C 键的加合物，从而在控制非对映选择性中起关键作用，得到氢化反应。具有立体特异性合成的产品-选择性。该协议提供了对手性 α-氟-β-氨基酯的有效访问，这些酯在有机合成和药物化学中具有重要的潜在应用。
• 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
• US6399787B1
  申请人：——

  公开号：US6399787B1

  公开（公告）日：2002-06-04
• [EN] CATALYTIC ASYMMETRIC HYDROGENATION, HYDROFORMYLATION, AND HYDROVINYLATION VIA TRANSITION METAL CATALYSTS WITH PHOSPHINES AND PHOSPHITES<br/>[FR] HYDROGENATION CATALYTIQUE ASYMETRIQUE, HYDROFORMULATION, ET HYDROVINYLATION VIA DES CATALYSEURS A METAUX DE TRANSITION AVEC PHOSPHINES ET PHOSPHITES
  申请人：THE PENN STATE RESEARCH FOUNDATION

  公开号：WO1999059721A1

  公开（公告）日：1999-11-25

  (EN) Novel transition metal catalysts with conformationally rigid chiral phosphines and phosphites are developed for asymmetric carbon-hydrogen and carbon-carbon bond formation. The invention emphasizes synthesis of chiral amines, $g(b)-amino acids and related compounds via catalytic asymmetric hydrogenation based on chiral monodentate and bidentate phosphines with cyclic ring structures. The ligands contain rigid ring structures.(FR) L'invention concerne l'élaboration de catalyseurs à métaux avec phosphines et phosphites de forme chirale à rigidité conformationnelle, pour la formation de liaisons asymétriques carbone-hydrogène et carbone-carbone. L'invention porte en particulier sur la synthèse d'amines chirales, de bêta-aminoacides et de composés connexes par hydrogénation catalytique asymétrique reposant sur des phosphines chirales monodentées et bidentées qui présentent des structures à noyau cyclique. Les ligands présentent des structures à noyau rigide.
• 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.