(R)-{methyl[2-(5-methylfuran-2-yl)-4-oxobutyl]amino}acetic acid tert-butyl ester | 1266318-09-5

• 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: (R)-{methyl[2-(5-methylfuran-2-yl)-4-oxobutyl]amino}acetic acid tert-butyl ester
• 英文别名: tert-butyl N-methyl-N-[(2R)-2-(5-methylfuran-2-yl)-4-oxobutyl]carbamate
• CAS: 1266318-09-5
• 化学式: C₁₅H₂₃NO₄
• 分子量: 281.352
• InChiKey: VEKWKJCIJRWTES-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  59.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-{methyl[2-(5-methylfuran-2-yl)-4-oxobutyl]amino}acetic acid tert-butyl ester 在 盐酸 、 甲醇 、 sodium tetrahydroborate 、 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：

  tert-butyl (E)-(4-hydroxybut-2-en-1-yl)(methyl)carbamate 在 盐酸 、 戴斯-马丁氧化剂 、 (2S,5S)-(-)-2-叔丁基-3-甲基-5-苯基-4-咪唑啉酮 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 38.0h， 生成 (R)-{methyl[2-(5-methylfuran-2-yl)-4-oxobutyl]amino}acetic 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

文献信息

• Enantioselective synthesis of 3-substituted tryptamines as core components of central nervous system drugs and indole natural products
  作者：Stephen Hanessian、Elia J.L. Stoffman

  DOI：10.1139/cjc-2012-0221

  日期：2013.1

  Application of the MacMillan iminium ion Michael and Friedel–Crafts type reactions to γ-amino α,β-unsaturated butanals led to the corresponding β-substituted butanals in good yields and high enantioselectivities. The products could be useful intermediates in the synthesis of indole-based central nervous system (CNS) drugs and natural products.

  麦克米伦亚胺离子迈克尔反应和弗里德尔-克拉夫茨类型反应在γ-氨基α，β-不饱和丁醛的应用，可得到相应的β-取代丁醛，收率良好，对映选择性高。该产品可用作合成基于吲哚的中枢神经系统（CNS）药物和天然产物的有用中间体。