N-tert-butyloxycarbonyl-4-methylamino-(E)-but-2-en-1-al | 1266317-87-6

• 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: N-tert-butyloxycarbonyl-4-methylamino-(E)-but-2-en-1-al
• 英文别名: tert-butyl N-methyl-N-[(E)-4-oxobut-2-enyl]carbamate
• CAS: 1266317-87-6
• 化学式: C₁₀H₁₇NO₃
• 分子量: 199.25
• InChiKey: LMXSHCZTHJXVLV-AATRIKPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-tert-butyloxycarbonyl-4-methylamino-(E)-but-2-en-1-al 在 盐酸 、 甲醇 、 sodium tetrahydroborate 、 (2S,5S)-(-)-2-叔丁基-3-甲基-5-苯基-4-咪唑啉酮 作用下， 以 乙酸乙酯 为溶剂， 反应 36.0h， 生成 tert-butyl (R)-(4-hydroxy-2-(5-methylfuran-2-yl)butyl)(methyl)carbamate
  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：

  N-Boc-(甲胺基)乙醛 在 sodium hydride 、 二异丁基氢化铝 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 mineral oil 为溶剂， 反应 3.17h， 生成 N-tert-butyloxycarbonyl-4-methylamino-(E)-but-2-en-1-al
  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

文献信息

• Applications of Organocatalytic Asymmetric Synthesis to Drug Prototypes—Dual Action and Selective Inhibitors of <i>n</i>-Nitric Oxide Synthase with Activity Against the 5-HT_1D/1B Subreceptors
  作者：Stephen Hanessian、Eli Stoffman、Xueling Mi、Paul Renton

  DOI：10.1021/ol102795g

  日期：2011.3.4

  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.