(S)-(-)-methyl 3-acetamido-5-methylhexanoate | 136744-89-3

• 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: (S)-(-)-methyl 3-acetamido-5-methylhexanoate
• 英文别名: (R)-methyl 5-methyl-3-acetamidohexanoate；methyl (3S)-3-acetamido-5-methylhexanoate
• CAS: 136744-89-3
• 化学式: C₁₀H₁₉NO₃
• 分子量: 201.266
• InChiKey: GEFIJIYCRPRTIV-VIFPVBQESA-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：

  (S)-(-)-methyl 3-acetamido-5-methylhexanoate 在 盐酸 作用下， 以 四氢呋喃 为溶剂， 反应 19.0h， 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 、 bis(1,5-cyclooctadiene)rhodium(I) trifluoromethanesulfonate 、 ammonium acetate 、 氢气 、 (2R,2'R)-bis(diphenylphosphino)-(1R,1'R)-dicyclopentane 作用下， 以 四氢呋喃 、 甲醇 、 甲苯 为溶剂， 20.0 ℃ 、275.79 kPa 条件下， 反应 120.0h， 生成 (S)-(-)-methyl 3-acetamido-5-methylhexanoate
  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

• 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 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.