tert-butyl (R)-(4-hydroxy-2-(5-methylfuran-2-yl)butyl)(methyl)carbamate | 1266318-14-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: tert-butyl (R)-(4-hydroxy-2-(5-methylfuran-2-yl)butyl)(methyl)carbamate
• CAS: 1266318-14-2
• 化学式: C₁₅H₂₅NO₄
• 分子量: 283.368
• InChiKey: PFVFLUHZJPESIN-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.92
• 重原子数：
  20.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  62.91
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  tert-butyl (R)-(4-hydroxy-2-(5-methylfuran-2-yl)butyl)(methyl)carbamate 、 (R)-methoxytrifluoromethylphenylacetyl chloride 在 盐酸 、 三乙胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 3.08h， 生成
  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：

  (R)-{methyl[2-(5-methylfuran-2-yl)-4-oxobutyl]amino}acetic acid tert-butyl ester 在 甲醇 、 sodium tetrahydroborate 作用下， 以63.9 mg的产率得到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