9-(2-aminoethyl)-2,3,6,7-tetrahydro-1H,5H,11H-[1]benzopyrano[6,7,8-ij]quinolizin-11-one trifluoroacetic acid salt | 1386264-38-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 9-(2-aminoethyl)-2,3,6,7-tetrahydro-1H,5H,11H-[1]benzopyrano[6,7,8-ij]quinolizin-11-one trifluoroacetic acid salt
• 英文别名: FFN511 TFA salt；6-(2-Aminoethyl)-3-oxa-13-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1(17),2(7),5,8-tetraen-4-one;2,2,2-trifluoroacetic acid；6-(2-aminoethyl)-3-oxa-13-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1(17),2(7),5,8-tetraen-4-one;2,2,2-trifluoroacetic acid
• CAS: 1386264-38-5
• 化学式: C₂HF₃O₂*C₁₇H₂₀N₂O₂
• 分子量: 398.382
• InChiKey: XHUSAIWAUAMZRG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.63
• 重原子数：
  28
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  92.9
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  9-(2-aminoethyl)-2,3,6,7-tetrahydro-1H,5H,11H-[1]benzopyrano[6,7,8-ij]quinolizin-11-one trifluoroacetic acid salt 在 碳酸氢钠 作用下， 以 水 为溶剂， 以96%的产率得到9-(2-aminoethyl)-2,3,6,7-tetrahydro-1H,5H,11H-[1]benzopyrano[6,7,8-ij]quinolizin-11-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-(tert-butoxycarbonylamino)pent-2-ynoic acid 在 4-二甲氨基吡啶 、 silver hexafluoroantimonate 、 三苯基膦氯金 、 N,N'-二异丙基碳二亚胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 2.25h， 生成 9-(2-aminoethyl)-2,3,6,7-tetrahydro-1H,5H,11H-[1]benzopyrano[6,7,8-ij]quinolizin-11-one trifluoroacetic acid salt
  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

文献信息

• 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.