8-(2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolizine) but-2-ynoate | 1386264-02-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 8-(2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolizine) but-2-ynoate
• 英文别名: 1-Azatricyclo[7.3.1.05,13]trideca-5,7,9(13)-trien-6-yl but-2-ynoate；1-azatricyclo[7.3.1.05,13]trideca-5,7,9(13)-trien-6-yl but-2-ynoate
• CAS: 1386264-02-3
• 化学式: C₁₆H₁₇NO₂
• 分子量: 255.316
• InChiKey: LBLZNFIEPAZVHK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  8-(2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolizine) but-2-ynoate 在 C₆₄H₁₀₈AuClN₂O₃₃ 作用下， 以 水 为溶剂， 反应 42.0h， 以52%的产率得到香豆素 102
  参考文献：
  名称：

  全甲基化NHC封端的a和b环糊精（ICyDMe）在纯水中的区域选择性和对映选择性金催化。

  摘要：

  开发了一系列基于NHC封端的全甲基化环糊精（ICyD Me）的水溶性包封的铜（I），银（I）或金（I）配合物，并将其用作纯水中的水合，内酯化，加氢芳基化和环异构化的催化剂反应。ICyD Me配体在加氢芳基化反应中具有基于腔的高区域选择性，在金催化的环异构化反应中具有高对映选择性，在水中可提供高达98％的 ee。因此，这些ICyD Me是在纯水中选择性催化的有用配体。

  DOI：

  10.1002/chem.202001990

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.
• Permethylated NHC‐Capped α‐ and β‐Cyclodextrins (ICyD ^Me ) Regioselective and Enantioselective Gold‐Catalysis in Pure Water
  作者：Xiaolei Zhu、Guangcan Xu、Lise‐Marie Chamoreau、Yongmin Zhang、Virginie Mouriès‐Mansuy、Louis Fensterbank、Olivia Bistri‐Aslanoff、Sylvain Roland、Matthieu Sollogoub

  DOI：10.1002/chem.202001990

  日期：2020.12.4

  A series of water‐soluble encapsulated copper(I), silver(I) or gold(I) complexes based on NHC‐capped permethylated cyclodextrins (ICyDMe) were developed and used as catalysts in pure water for hydration, lactonization, hydroarylation and cycloisomerization reactions. ICyDMe ligands gave cavity‐based high regioselectivity in hydroarylations, and high enantioselectivities in gold‐catalyzed cycloisomerizations

  开发了一系列基于NHC封端的全甲基化环糊精（ICyD Me）的水溶性包封的铜（I），银（I）或金（I）配合物，并将其用作纯水中的水合，内酯化，加氢芳基化和环异构化的催化剂反应。ICyD Me配体在加氢芳基化反应中具有基于腔的高区域选择性，在金催化的环异构化反应中具有高对映选择性，在水中可提供高达98％的 ee。因此，这些ICyD Me是在纯水中选择性催化的有用配体。