(R)-3-(1-(4-methoxybenzyloxy)-4-azidobutan-2-yl)-5-bromo-1H-indole | 1266317-83-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (R)-3-(1-(4-methoxybenzyloxy)-4-azidobutan-2-yl)-5-bromo-1H-indole
• 英文别名: 3-[(2R)-4-azido-1-[(4-methoxyphenyl)methoxy]butan-2-yl]-5-bromo-1H-indole
• CAS: 1266317-83-2
• 化学式: C₂₀H₂₁BrN₄O₂
• 分子量: 429.316
• InChiKey: REHXRFFQMATFAG-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  48.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-3-(1-(4-methoxybenzyloxy)-4-azidobutan-2-yl)-5-bromo-1H-indole 在 三氟化硼乙醚 、 水 、 sodium hydride 、 苯硫酚 、 三乙胺 、 三苯基膦 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 mineral oil 为溶剂， 反应 13.5h， 生成 (R)-5-bromo-3-(1-methylpyrrolidin-3-yl)-1H-indole
  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)-4-(4-methoxybenzyloxy)-3-(5-bromo-1H-indol-3-yl)butan-1-ol 在 偶氮二甲酸二异丙酯 、 三苯基膦 、 叠氮磷酸二苯酯 作用下， 以 四氢呋喃 为溶剂， 反应 0.17h， 以72%的产率得到(R)-3-(1-(4-methoxybenzyloxy)-4-azidobutan-2-yl)-5-bromo-1H-indole
  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.