(R)-5-bromo-3-pyrrolidin-3-yl-1H-indole | 1266317-98-9

• 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)-5-bromo-3-pyrrolidin-3-yl-1H-indole
• 英文别名: 5-bromo-3-[(3R)-pyrrolidin-3-yl]-1H-indole
• CAS: 1266317-98-9
• 化学式: C₁₂H₁₃BrN₂
• 分子量: 265.153
• InChiKey: REHOOAFJZMXJJN-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  27.8
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  聚合甲醛 、 (R)-5-bromo-3-pyrrolidin-3-yl-1H-indole 在 sodium cyanoborohydride 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以127 mg的产率得到(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)-tert-butyl-3-(5-bromo-1H-indol-3-yl)pyrrolidine-1-carboxylate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 (R)-5-bromo-3-pyrrolidin-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

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。
• 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.