methyl (Z)-2-acetamido-4-(methoxymethylphosphinyl)but-2-enoate | 131131-79-8

• 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 (Z)-2-acetamido-4-(methoxymethylphosphinyl)but-2-enoate
• 英文别名: methyl (Z)-2-acetamido-4-[methoxy(methyl)phosphoryl]but-2-enoate
• CAS: 131131-79-8
• 化学式: C₉H₁₆NO₅P
• 分子量: 249.203
• InChiKey: QKYRKWKCYGCBJI-YVMONPNESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  81.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl (Z)-2-acetamido-4-(methoxymethylphosphinyl)but-2-enoate 以99%的产率得到
  参考文献：
  名称：

  ZEISS, HANS-JOACHIM, J. ORG. CHEM., 56,(1991) N, C. 1783-1788

  摘要：

  DOI：
• 作为产物：
  描述：

  2-羰基-4-(羟基甲基膦酰基)丁酸 在 对甲苯磺酸 作用下， 以 溶剂黄146 为溶剂， 反应 9.08h， 生成 methyl (Z)-2-acetamido-4-(methoxymethylphosphinyl)but-2-enoate
  参考文献：
  名称：

  Enantioselective synthesis of both enantiomers of phosphinothricin via asymmetric hydrogenation of .alpha.-acylamido acrylates

  摘要：

  Both enantiomers of phosphinothricin (1), a naturally occuring amino acid that contains the unique methylphosphinate moiety, were prepared by asymmetric hydrogenation of alpha-acylamido acrylate precursors 7. L-1 and peptides containing L-1 are inhibitors of the enzyme glutamine synthetase (GS). Inhibition of GS is responsible for the antibiotical and herbicidal properties of these compounds. Synthesis of substrates 7 and parameters influencing the enantioselectivity are discussed. Substrate concentration and solvent polarity appear to have the most marked effects on enantiomeric excesses for a given catalyst system. Enantiomeric excesses reach 91 % for hydrogenations with (R,R)-NORPHOS- and (S,S)-CHIRAPHOS-derived catalysts.

  DOI：

  10.1021/jo00005a024

文献信息

• Verfahren zur Herstellung von L-Phosphinothricin(derivaten) sowie ihrer Alkylester
  申请人：HOECHST AKTIENGESELLSCHAFT

  公开号：EP0238954A2

  公开（公告）日：1987-09-30

  Verfahren zur Herstellung von L-Phosphinothricin(derivaten) durch homogene asymmetrische Hydrierung von 2,3-Dehydrophosphinothricin(derivaten) mittels geeigneter Ruthenium-, Rhodium-oder Iridiumkatalysatoren.

  使用合适的钌、铑或铱催化剂，通过 2,3-脱氢磷霉素（衍生物）的均相不对称氢化制备 L-磷霉素（衍生物）的工艺。
• METHOD FOR PRODUCING L-2-AMINO-4-(HYDROXYMETHYLPHOSPHINYL)- BUTANOIC ACID
  申请人：Meiji Seika Pharma Co., Ltd.

  公开号：EP1864989B1

  公开（公告）日：2012-07-18
• Method for Producing L-2-Amino-4-(Hydroxymethylphosphinyl)-Butanoic Acid
  申请人：Minowa Nobuto

  公开号：US20080146837A1

  公开（公告）日：2008-06-19

  Disclosed is a method for efficiently and highly selectively producing L-2-amino-4-(hydroxymethylphosphinyl)-butanoic acid, which is useful as a herbicide, through a catalytic asymmetric synthesis reaction. Specifically disclosed is a method for producing L-2-amino-4-(hydroxymethylphosphinyl)-butanoic acid which is characterized in that a dehydroamino acid is subjected to an asymmetric hydrogenation by using a rhodium catalyst represented by the formula (2) below and having an optically active cyclic phosphine ligand, and then the resulting product is subjected to hydrolysis: [Rh(R 4 )(L)]X   (2) [where R 4 represents 1,5-cyclooctadien or norbornadien; L represents a substance represented by the following formula (6): (wherein R 5 and R 8 respectively represent a C 1-4 alkyl group; R 6 and R 7 respectively represent hydrogen atom or hydroxyl group; and Y represents a group selected from groups represented by the following formula (7): (where Me represents methyl group)).].
• US4922006A
  申请人：——

  公开号：US4922006A

  公开（公告）日：1990-05-01
• US7772426B2
  申请人：——

  公开号：US7772426B2

  公开（公告）日：2010-08-10