N-tert-butyloxycarbonyl-4-methylamino-(E)-but-2-enoic acid ethyl ester | 149650-08-8

• 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: N-tert-butyloxycarbonyl-4-methylamino-(E)-but-2-enoic acid ethyl ester
• 英文别名: (E)-Ethyl 4-((tert-butoxycarbonyl)(methyl)amino)but-2-enoate；ethyl (E)-4-[methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]but-2-enoate
• CAS: 149650-08-8
• 化学式: C₁₂H₂₁NO₄
• 分子量: 243.303
• InChiKey: SBZUSLOEYRVCLL-BQYQJAHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 危险性防范说明：
  P264,P280,P302+P352,P337+P313,P305+P351+P338,P362+P364,P332+P313
• 危险性描述：
  H315,H319

反应信息

• 作为反应物：
  描述：

  N-tert-butyloxycarbonyl-4-methylamino-(E)-but-2-enoic acid ethyl ester 在 甲醇 、 sodium tetrahydroborate 、 二异丁基氢化铝 、 戴斯-马丁氧化剂 、 (2S,5S)-(-)-2-叔丁基-3-甲基-5-苯基-4-咪唑啉酮 、 三氟乙酸 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 异丙醇 为溶剂， 反应 28.5h， 生成 (S)-[2-(5-bromo-1H-indol-3-yl)-4-hydroxybutyl](methyl)carbamic acid tert-butyl ester
  参考文献：
  名称：

  Applications of Organocatalytic Asymmetric Synthesis to Drug Prototypes—Dual Action and Selective Inhibitors of n-Nitric Oxide Synthase with Activity Against the 5-HT_1D/1B Subreceptors

  摘要：

  The scope of MacMillan's organocatalytic asymmetric conjugate addition reaction of indoles and electron-rich aromatics to alpha,beta-unsaturated aldehydes has been extended to the use of 3-amino crotonaldehydes as substrates. The aromatics used include indoles as well as an aniline and a furan. The scope and effect of the groups on nitrogen (R, R') has also been studied. The method has been applied to the concise synthesis of an advanced precursor to S-(+)-1, a drug prototype for the treatment of migraine headaches.

  DOI：

  10.1021/ol102795g
• 作为产物：
  描述：

  磷酰基乙酸三乙酯 、 N-Boc-(甲胺基)乙醛 在 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 0.67h， 生成 N-tert-butyloxycarbonyl-4-methylamino-(E)-but-2-enoic acid ethyl ester
  参考文献：
  名称：

  Applications of Organocatalytic Asymmetric Synthesis to Drug Prototypes—Dual Action and Selective Inhibitors of n-Nitric Oxide Synthase with Activity Against the 5-HT_1D/1B Subreceptors

  摘要：

  The scope of MacMillan's organocatalytic asymmetric conjugate addition reaction of indoles and electron-rich aromatics to alpha,beta-unsaturated aldehydes has been extended to the use of 3-amino crotonaldehydes as substrates. The aromatics used include indoles as well as an aniline and a furan. The scope and effect of the groups on nitrogen (R, R') has also been studied. The method has been applied to the concise synthesis of an advanced precursor to S-(+)-1, a drug prototype for the treatment of migraine headaches.

  DOI：

  10.1021/ol102795g