N-(p-toluenesulfonyl)-α-dehydrovaline | 863912-72-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(p-toluenesulfonyl)-α-dehydrovaline
• 英文别名: 3-Methyl-2-[(4-methylphenyl)sulfonylamino]but-2-enoic acid
• CAS: 863912-72-5
• 化学式: C₁₂H₁₅NO₄S
• 分子量: 269.321
• InChiKey: AAOXKCCHHUFFMO-UHFFFAOYSA-N

物化性质

• 熔点：
  188.5-189.5 °C
• 沸点：
  467.9±55.0 °C(Predicted)
• 密度：
  1.281±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  91.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(p-toluenesulfonyl)-α-dehydrovaline 在 C₄₆H₄₆ClP₂RuS₂⁽¹⁺⁾*Cl^(1-) 氢气 作用下， 以 乙醇 为溶剂， 25.0 ℃ 、721.87 kPa 条件下， 反应 24.0h， 以99%的产率得到N-对甲苯磺酰基-D-缬氨酸
  参考文献：
  名称：

  [EN] PROCESS FOR MAKING N-SULFONATED-AMINO ACID DERIVATIVES
  [FR] PROCEDE DE FABRICATION DE DERIVES D'ACIDES AMINES N-SULFONES

  摘要：

  公开号：

  WO2005118529A3
• 作为产物：
  描述：

  3-甲基-2-氧代丁酰乙酯 在 lithium hydroxide 、 甲烷磺酸 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 24.0h， 生成 N-(p-toluenesulfonyl)-α-dehydrovaline
  参考文献：
  名称：

  Asymmetric Hydrogenation of N-Sulfonylated-α-dehydroamino Acids:  Toward the Synthesis of an Anthrax Lethal Factor Inhibitor

  摘要：

  [GRAPHIC]A novel and highly enantioselective Ru-catalyzed hydrogenation of N-sulfonylated-alpha-dehydroamino acids has been discovered and demonstrated in the synthesis of an anthrax lethal factor inhibitor (LFI). Herein, this methodology is used to prepare N-sulfonylated amino acids in up to 98% ee. This unprecedented hydrogenation uses a chiral Ru catalyst rather than Rh as typical for acylated dehydroamino acids and esters, and this work reports the first asymmetric hydrogenation of a tetrasubstituted dehydroamino acid derivative using a Ru catalyst.

  DOI：

  10.1021/ol050869s

文献信息

• Process For Making N-Sulfonated-Amino Acid Derivatives
  申请人：Dreher D. Spencer

  公开号：US20070219382A1

  公开（公告）日：2007-09-20

  This invention relates to a process for preparing optically active α-amino acid substrates which are used to make potent lethal factor (LF) inhibitors for the treatment of anthrax. This invention further relates to a process for synthesis of potent LF-inhibitors for the treatment of anthrax. Specifically, the invention concerns a novel, high-yielding and highly enantioselective asymmetric hydrogenation reaction of a tetrasubstituted ene-sulfonamide acid or ester.
• US7579487B2
  申请人：——

  公开号：US7579487B2

  公开（公告）日：2009-08-25
• [EN] PROCESS FOR MAKING N-SULFONATED-AMINO ACID DERIVATIVES<br/>[FR] PROCEDE DE FABRICATION DE DERIVES D'ACIDES AMINES N-SULFONES
  申请人：MERCK & CO INC

  公开号：WO2005118529A3

  公开（公告）日：2006-02-16
• Asymmetric Hydrogenation of <i>N</i>-Sulfonylated-α-dehydroamino Acids:  Toward the Synthesis of an Anthrax Lethal Factor Inhibitor
  作者：C. Scott Shultz、Spencer D. Dreher、Norihiro Ikemoto、J. Michael Williams、Edward J. J. Grabowski、Shane W. Krska、Yongkui Sun、Peter G. Dormer、Lisa DiMichele

  DOI：10.1021/ol050869s

  日期：2005.8.1

  [GRAPHIC]A novel and highly enantioselective Ru-catalyzed hydrogenation of N-sulfonylated-alpha-dehydroamino acids has been discovered and demonstrated in the synthesis of an anthrax lethal factor inhibitor (LFI). Herein, this methodology is used to prepare N-sulfonylated amino acids in up to 98% ee. This unprecedented hydrogenation uses a chiral Ru catalyst rather than Rh as typical for acylated dehydroamino acids and esters, and this work reports the first asymmetric hydrogenation of a tetrasubstituted dehydroamino acid derivative using a Ru catalyst.