(3bR,6aR,9aS,12aS)-2-chloro-3b,5,6,6a,9a,10,11,12a-octahydro-7H,9H-furo[3,2-c]furo[2′,3′:4,5]pyrido[3,2,1-ij]quinoline

• 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: (3bR,6aR,9aS,12aS)-2-chloro-3b,5,6,6a,9a,10,11,12a-octahydro-7H,9H-furo[3,2-c]furo[2′,3′:4,5]pyrido[3,2,1-ij]quinoline
• 英文别名: (3bR,6aR,9aS,12aS)-2-chloro-3b,5,6,6a,9a,10,11,12a-octahydro-7H,9H-furo[3,2-c]furo[2',3':4,5]pyrido[3,2,1-ij]quinoline；(3S,7S,13R,17R)-10-chloro-6,14-dioxa-1-azapentacyclo[10.6.1.03,7.08,19.013,17]nonadeca-8,10,12(19)-triene
• 化学式: C₁₆H₁₈ClNO₂
• 分子量: 291.777
• InChiKey: KIWRAPZZBIVKSJ-DICSFEIXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  21.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2,3-二氢呋喃 、 聚合甲醛 、 对氯苯胺 在 silica-supported p-sulfonic acid calix[4]arene heterogeneous catalyst CX₄SO₃HSi(n) 作用下， 以 neat (no solvent) 为溶剂， 反应 0.17h， 以48%的产率得到(3bR,6aR,9aR,12aR)-2-chloro-3b,5,6,6a,9a,10,11,12a-octahydro-7H,9H-furo[3,2-c]furo[2′,3′:4,5]pyrido[3,2,1-ij]quinoline
  参考文献：
  名称：

  以二氧化硅为支撑的杯芳烃[4]芳烃为多相催化剂，微波辅助合成氟尿嘧啶核苷

  摘要：

  已经描述了使用溶胶-凝胶法将杯芳烃固定在二氧化硅表面上作为用于多组分Povarov反应的有效多相催化剂（CX4SO 3 HSi（n））的应用。CX4SO 3 HSi（n的催化活性）在绿色和环境友好的条件下，以简单有效的方法合成了聚四氢吡啶。值得注意的是，仅0.5mol％的催化剂足以在微波辅助下催化无Povarov溶剂的反应。此外，该协议允许在一个步骤中构建四个新的C–C键和两个C–N键。据我们所知，这是第一个二氧化硅载体杯[4]芳烃，它是一种多聚体合成julolidines的非均相催化剂。

  DOI：

  10.1016/j.tet.2019.05.049

文献信息

• GOLD-POLYMER NANOSTRUCTURE-IMMOBILIZED SCANDIUM CATALYST AND ITS USE
  申请人：Kobayashi Shu

  公开号：US20130059999A1

  公开（公告）日：2013-03-07

  The present invention provides a Scandium catalyst that can be used in water or water-soluble organic solvent with no leaching of Scandium. Provided is a gold-polymer nanostructure-immobilized Scandium catalyst, which is formed by preparing, in liquid phase, a mixture comprising gold clusters with from 1 to 50 nm of diameter, disulfide monomer, sulfonic acid salt of disulfide and Lewis acid metal compound represented by ScY 3 , wherein Y is OSO 2 CF 3 etc., and polymerizing the mixture in the presence of a radical polymerization initiator, wherein the disulfide monomer is represented by the formula below: CH 2 ═CH—R 1 —S—S—R 1 —CH═CH 2 wherein R 1 represents a divalent hydrocarbon, which may contain an ether bond, and the sulfonic acid salt of disulfide is represented by the formula below: MO 3 S—R 2 —S—S—R 2 —SO 3 M wherein R 2 represents a divalent hydrocarbon, which may contain an ether bond, and M represents an alkali metal. This catalyst is useful as a catalyst for aldol reactions, cyanolation reactions, allylation reactions, Michael reactions, Mannich reactions, Diels Alder reactions and Friedel Crafts reactions in water or water-soluble organic solvent.

  本发明提供了一种可以在水或水溶性有机溶剂中使用的钪催化剂，不会出现钪的淋出。所提供的是一种金聚合物纳米结构固定的钪催化剂，该催化剂是通过在液相中制备混合物形成的，该混合物包括直径为1至50纳米的金团簇、二硫化物单体、二硫化物磺酸盐和由ScY3表示的Lewis酸金属化合物，其中Y为OSO2CF3等，然后在自由基引发剂的存在下聚合该混合物，其中二硫化物单体由下式表示：CH2═CH—R1—S—S—R1—CH═CH2，其中R1表示一个二价碳氢化合物，可以包含醚键，二硫化物磺酸盐由下式表示：MO3S—R2—S—S—R2—SO3M，其中R2表示一个二价碳氢化合物，可以包含醚键，M表示一种碱金属。该催化剂可用作水或水溶性有机溶剂中的醛基反应、氰化反应、烯丙基化反应、迈克尔反应、曼尼希反应、Diels Alder反应和Friedel Crafts反应的催化剂。
• Calix[<i>n</i>]arene-Catalyzed Three-Component Povarov Reaction: Microwave-Assisted Synthesis of Julolidines and Mechanistic Insights
  作者：Paula Aline da Silva Abranches、Walysson Ferreira de Paiva、Ângelo de Fátima、Felipe Terra Martins、Sergio Antonio Fernandes

  DOI：10.1021/acs.joc.7b02532

  日期：2018.2.16

  A new one-pot cascade reaction-based application of Povarov reactions with a p-sulfonic acid calix[4]arene catalyst for the synthesis of a series of 34 julolidine derivatives with substituents at C8 or C9 in good to excellent yields is reported. These microwave-assisted reactions proceeded efficiently, had short reaction times, were metal-free, were low cost, and used an inexpensive, easily available and nontoxic catalyst. These advantages, along with a simple workup procedure, make this protocol a very efficient and green alternative to the traditional methods for constructing these types of N-heterocyclic skeletons. In addition, this protocol allows the formation of julolidine structures, which requires the construction of four new C-C bonds and two C-N bonds. A mechanism for the Povarov reaction involving a stepwise sequence via ionic intermediates was proposed and validated.
• GOLD POLYMER NANO-STRUCTURE-SUPPORTED SCANDIUM CATALYST AND USE OF THE SAME
  申请人：Japan Science and Technology Agency

  公开号：EP2545991B1

  公开（公告）日：2014-06-04
• US8735522B2
  申请人：——

  公开号：US8735522B2

  公开（公告）日：2014-05-27
• Microwave-assisted multicomponent synthesis of julolidines using silica-supported calix[4]arene as heterogeneous catalyst
  作者：Walysson Ferreira de Paiva、Ingredy Bastos Braga、João Vitor de Assis、Sandra Milena Bonilla Castañeda、Ángel Gabriel Sathicq、Valeria Palermo、Gustavo Pablo Romanelli、Ricardo Natalino、Marcio José da Silva、Felipe Terra Martins、Gustavo Senra Gonçalves de Carvalho、Giovanni Wilson Amarante、Sergio Antonio Fernandes

  DOI：10.1016/j.tet.2019.05.049

  日期：2019.7

  sol-gel method, as an efficient heterogeneous catalyst (CX4SO3HSi(n)) for multicomponent Povarov reaction has been described. Catalytic activity of the CX4SO3HSi(n) for the synthesis of julolidines under greener and environmentally benign conditions in simple and efficient method was explored. Notably, only 0.5 mol% of the catalyst is sufficient to catalyze the Povarov solvent-free reaction under microwave-assistance

  已经描述了使用溶胶-凝胶法将杯芳烃固定在二氧化硅表面上作为用于多组分Povarov反应的有效多相催化剂（CX4SO 3 HSi（n））的应用。CX4SO 3 HSi（n的催化活性）在绿色和环境友好的条件下，以简单有效的方法合成了聚四氢吡啶。值得注意的是，仅0.5mol％的催化剂足以在微波辅助下催化无Povarov溶剂的反应。此外，该协议允许在一个步骤中构建四个新的C–C键和两个C–N键。据我们所知，这是第一个二氧化硅载体杯[4]芳烃，它是一种多聚体合成julolidines的非均相催化剂。