1H-indol-5-yl but-2-ynoate | 878672-83-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: 1H-indol-5-yl but-2-ynoate
• 英文别名: but-2-ynoic acid 1H-indol-5-yl ester
• CAS: 878672-83-4
• 化学式: C₁₂H₉NO₂
• 分子量: 199.209
• InChiKey: WGKXSIDNRXBOLE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  42.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1H-indol-5-yl but-2-ynoate 在 氯化铂 作用下， 以 1,4-二氧六环 、 1,2-二氯乙烷 为溶剂， 以54%的产率得到9-methylpyrano[3,2-e]indol-7(3H)-one
  参考文献：
  名称：

  Catalytic Coupling of Arene C–H Bonds and Alkynes for the Synthesis of Coumarins: Substrate Scope and Application to the Development of Neuroimaging Agents

  摘要：

  C-H bond functionalization offers strategically novel approaches to complex organic compounds. However, many C-H functionalization reactions suffer from poor compatibility with Lewis basic functional groups, especially amines, which are often essential for biological activity. This study describes a systematic examination of the substrate scope of catalytic hydroarylation in the context of complex amino coumarin synthesis. The choice of substrates was guided by the design and development of the next generation of fluorescent false neurotransmitters (FFNs), neuroimaging probes we recently introduced for optical imaging of neurotransmission in the brain. Comparison of two mild protocols using catalytic PtCl4 or Au(PPh3)Cl/AgSbF6 revealed that each method has a broad and mutually complementary substrate scope. The relatively less active platinum system out-performed the gold catalyst with indole substrates lacking substitution at the C-3 position and provided higher regioselectivity in the case of carbazole-based substrates. On the other hand, the more active gold catalyst demonstrated excellent functional group tolerance, and the ability to catalyze the formation of strained, helical products. The development of these two protocols offers enhanced substrate scope and provides versatile synthetic tools required for the structure-activity examination of FFN neuroimaging probes as well as for the synthesis of complex coumarins in general.

  DOI：

  10.1021/jo3006842
• 作为产物：
  描述：

  5-羟基吲哚 、 2-丁炔酸 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 以55%的产率得到1H-indol-5-yl but-2-ynoate
  参考文献：
  名称：

  [EN] DEVELOPMENT OF FLUOROGENIC SUBSTRATES FOR MONOAMINE OXIDASES (MAO-A AND MAO-B)
  [FR] MISE AU POINT DE SUBSTRATS FLUOROGENES DESTINES AUX MONOAMINE OXYDASES (MAO-A AND MAO-B)

  摘要：

  公开号：

  WO2006026368A3

文献信息

• Development of Fluorogenic Substrates For Monoamine Oxidases (Mao-A and Mao-B)
  申请人：Chen Gong

  公开号：US20080194522A1

  公开（公告）日：2008-08-14

  The present invention relates to compounds useful for detecting the activity of monoamine oxidases, compounds useful for competitively inhibiting monoamine oxidases, for determining inhibitors of monoamine oxidases and compounds useful for treating monoamine oxidase-related nervous system pathologies, as well as pharmaceutical compositions and methods of manufacture thereof.

  本发明涉及用于检测单胺氧化酶活性的化合物，用于竞争性抑制单胺氧化酶的化合物，用于确定单胺氧化酶抑制剂和用于治疗与单胺氧化酶相关的神经系统病理的化合物，以及制药组合物和制造方法。
• [EN] DEVELOPMENT OF FLUOROGENIC SUBSTRATES FOR MONOAMINE OXIDASES (MAO-A AND MAO-B)<br/>[FR] MISE AU POINT DE SUBSTRATS FLUOROGENES DESTINES AUX MONOAMINE OXYDASES (MAO-A AND MAO-B)
  申请人：F NEW YORK THE TRUSTEES OF COL

  公开号：WO2006026368A3

  公开（公告）日：2006-08-31
• Catalytic Coupling of Arene C–H Bonds and Alkynes for the Synthesis of Coumarins: Substrate Scope and Application to the Development of Neuroimaging Agents
  作者：Paul A. Vadola、Dalibor Sames

  DOI：10.1021/jo3006842

  日期：2012.9.21

  C-H bond functionalization offers strategically novel approaches to complex organic compounds. However, many C-H functionalization reactions suffer from poor compatibility with Lewis basic functional groups, especially amines, which are often essential for biological activity. This study describes a systematic examination of the substrate scope of catalytic hydroarylation in the context of complex amino coumarin synthesis. The choice of substrates was guided by the design and development of the next generation of fluorescent false neurotransmitters (FFNs), neuroimaging probes we recently introduced for optical imaging of neurotransmission in the brain. Comparison of two mild protocols using catalytic PtCl4 or Au(PPh3)Cl/AgSbF6 revealed that each method has a broad and mutually complementary substrate scope. The relatively less active platinum system out-performed the gold catalyst with indole substrates lacking substitution at the C-3 position and provided higher regioselectivity in the case of carbazole-based substrates. On the other hand, the more active gold catalyst demonstrated excellent functional group tolerance, and the ability to catalyze the formation of strained, helical products. The development of these two protocols offers enhanced substrate scope and provides versatile synthetic tools required for the structure-activity examination of FFN neuroimaging probes as well as for the synthesis of complex coumarins in general.