9-(4-nitrobenzenesulfonyl)-1,4-dihydro-1,4-epiazano-naphthalene | 337377-24-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 9-(4-nitrobenzenesulfonyl)-1,4-dihydro-1,4-epiazano-naphthalene
• 英文别名: 9-((4-Nitrophenyl)sulfonyl)-1,4-dihydro-1,4-epiminonaphthalene；11-(4-nitrophenyl)sulfonyl-11-azatricyclo[6.2.1.02,7]undeca-2,4,6,9-tetraene
• CAS: 337377-24-9
• 化学式: C₁₆H₁₂N₂O₄S
• 分子量: 328.348
• InChiKey: QBEUZZOFAZMMBU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  91.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  9-(4-nitrobenzenesulfonyl)-1,4-dihydro-1,4-epiazano-naphthalene 、 苯乙炔 在 (S)-联萘(3,5-二甲苯基)膦 、 (CuOTf)*toluene 、 palladium diacetate 作用下， 以 乙二醇二甲醚 为溶剂， 反应 160.5h， 以61%的产率得到4-nitro-N-((1R,2S)-2-(phenylethynyl)-1,2-dihydronaphthalen-1-yl)benzenesulfonamide
  参考文献：
  名称：

  钯/铜配合物共同催化氮杂苯并降冰片二烯与末端炔烃的高对映选择性开环反应

  摘要：

  AbstractA chiral palladium/copper (Pd/Cu) co‐catalytic system which could enable asymmetric ring opening reaction of azabenzonorbornadienes with terminal alkynes is reported. This system comprises palladium(II) acetate [Pd(OAc)2]/(R)‐xyl‐Binap and copper(I) triflate (CuOTf). A good substrate scope was found, with excellent enantioselective outcomes (up to >99.9 % ee). A reaction mechanism involving two metal complexes is also proposed.magnified image

  DOI：

  10.1002/adsc.201300748

文献信息

• Rh-Catalyzed Highly Enantioselective Hydroalkynylation Reaction of Norbornadiene Derivatives
  作者：Baomin Fan、Jianbin Xu、Qingjing Yang、Sifeng Li、Hualei Chen、Shanshan Liu、Lu Yu、Yongyun Zhou、Lin Wang

  DOI：10.1021/ol402804t

  日期：2013.12.6

  The complexes of various Rh precusors with ferrocenyl chiral ligand (R,S)-Cy2PF-PPh2 were found effective catalysts for the asymmetric hydroalkynylation reaction of norbornadiene derivatives. When RhCl3·3H2O was employed, good yields (up to 98%) and high enantioselectivities (up to >99.9% ee) could be obtained for the reactions of a broad scope of substrates.

  发现各种Rh前体与二茂铁基手性配体（R，S）-Cy 2 PF-PPh 2的配合物是降冰片二烯衍生物不对称加氢烷基化反应的有效催化剂。当使用RhCl 3 ·3H 2 O时，对于广泛范围的底物反应，可以获得良好的产率（高达98％）和高的对映选择性（高达> 99.9％ee）。
• Rhodium(III)-Catalyzed Coupling of Arenes with 7-Oxa/Azabenzonorbornadienes by CH Activation
  作者：Zisong Qi、Xingwei Li

  DOI：10.1002/anie.201303507

  日期：2013.8.19

  Under chelation assistance, rhodium(III) complexes can catalyze the redox‐neutral coupling of arenes with 7‐oxabenzonorbornadienes and the oxidative coupling of arenes with 7‐azabenzonorbornadienes (see scheme; Cp*=C5Me5). A seven‐membered rhodacycle containing a RhC(alkyl) bond has been established as the key intermediate.

  在螯合辅助下，铑（III）络合物可以催化芳烃与7-氧杂苯并降冰片二烯的氧化还原-中性偶联，以及芳烃与7-氮杂苯并降冰片二烯的氧化偶联（见方案； Cp * = C 5 Me 5）。含有RH的七元rhodacycle  C（烷基）键已被确立为关键中间体。
• The Use of Silyl Ketene Acetals and Enol Ethers in the Catalytic Enantioselective Alkylative Ring Opening of Oxa/Aza Bicyclic Alkenes
  作者：Lei Zhang、Christine M. Le、Mark Lautens

  DOI：10.1002/anie.201400218

  日期：2014.6.2

  Silyl ketene acetals and enol ethers are employed as reactive and functional group tolerant nucleophiles in the enantioselective rhodium‐catalyzed alkylative ring opening of a diverse class of oxa/azabicyclic alkenes. This method provides access to enantioenriched dihydronaphthalene and cyclohexene scaffolds, which have the potential to be derivatized toward core motifs of naphthoquinone and sesquiterpene

  甲硅烷基乙烯酮缩醛和烯醇醚在各种类型的氧杂/氮杂双环烯烃的对映体选择性铑催化的烷基化开环中用作反应性和官能团耐受性亲核试剂。该方法提供了对映体富集的二氢萘和环己烯支架的途径，它们有可能被衍生为萘醌和倍半萜天然产物的核心图案。
• Novel compounds and a novel process for their preparation
  申请人：Fagnou Keith

  公开号：US20080300271A1

  公开（公告）日：2008-12-04

  The present invention is directed to a procedure for making an enantidimerically enriched compound containing a hydronaphthalene ring structure. The process involves reacting oxabenzonorbornadienes with nuclophiles using rhodium as a catalyst and in the presence of a phosphine ligand. The compounds synthesized may be used in pharmaceutical preparations for the treatment of a variety of diseases and conditions.

  本发明涉及一种制备含有氢化萘环结构的对映二聚体富集化合物的方法。该过程涉及使用铑作为催化剂，以及存在膦配体下的氧化苯并[2.2.1]庚二烯与亲核试剂反应。合成的化合物可用于制备治疗各种疾病和病况的制药制剂。
• US7420003B2
  申请人：——

  公开号：US7420003B2

  公开（公告）日：2008-09-02