cis-N,N'-bis-(prop-2-ynyl)-N,N'-bis-(p-toluenesulfonyl)-1,2-diaminocyclohex-4-ene | 934389-61-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: cis-N,N'-bis-(prop-2-ynyl)-N,N'-bis-(p-toluenesulfonyl)-1,2-diaminocyclohex-4-ene
• 英文别名: 4-methyl-N-[(1S,6R)-6-[(4-methylphenyl)sulfonyl-prop-2-ynylamino]cyclohex-3-en-1-yl]-N-prop-2-ynylbenzenesulfonamide
• CAS: 934389-61-4
• 化学式: C₂₆H₂₈N₂O₄S₂
• 分子量: 496.651
• InChiKey: LOMQNVWVKCMMND-WMPKNSHKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  91.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  cis-N,N'-bis-(prop-2-ynyl)-N,N'-bis-(p-toluenesulfonyl)-1,2-diaminocyclohex-4-ene 、 乙烯 在 Grubbs catalyst first generation 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 以16%的产率得到(R)-1,2,3,6-tetrahydro-2-((S)-1,2,3,6-tetrahydro-1-tosyl-5-vinylpyridin-2-yl)-1-tosyl-5-vinylpyridine
  参考文献：
  名称：

  Alkene and enyne metathesis reactions on allylic and propargylic amines

  摘要：

  Treatment of cis-4,5-diaminocyclohexene derivatives bearing allyl or propargyl groups on the nitrogen atoms, with first or second generation Grubbs metathesis catalysts, results in initiation of metathesis cascades which include ring-opening of the unstrained cyclohexene ring. This contrasts with the previous work on the analogous cyclohexene ethers where metathesis reactions occurred exclusively between the side-chains and no ring-opening of the cyclohexene unit was observed. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.01.092
• 作为产物：
  描述：

  cis-4,5-diaminocyclohexene dihydrochloride 在 sodium hydride 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 cis-N,N'-bis-(prop-2-ynyl)-N,N'-bis-(p-toluenesulfonyl)-1,2-diaminocyclohex-4-ene
  参考文献：
  名称：

  Alkene and enyne metathesis reactions on allylic and propargylic amines

  摘要：

  Treatment of cis-4,5-diaminocyclohexene derivatives bearing allyl or propargyl groups on the nitrogen atoms, with first or second generation Grubbs metathesis catalysts, results in initiation of metathesis cascades which include ring-opening of the unstrained cyclohexene ring. This contrasts with the previous work on the analogous cyclohexene ethers where metathesis reactions occurred exclusively between the side-chains and no ring-opening of the cyclohexene unit was observed. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.01.092

文献信息

• Synthesis of N-heterocyclic compounds via ene–yne metathesis reactions
  作者：Elisabetta Groaz、Donatella Banti、Michael North

  DOI：10.1016/j.tet.2007.10.076

  日期：2008.1

  Propargylamino and allylamino derivatives of cyclohexene and norbornene were subjected to tandem metathesis reactions with first and second generation Grubbs' catalysts 1 and 2. Results show that the method is compatible with suitably protected nitrogen-containing compounds. Cyclohexenes gave intriguing results in terms of the possibility to perform ring rearrangement metathesis (RRM) reactions, showing a difference with the analogous allyl and propargyl ether substrates. (c) 2007 Elsevier Ltd. All rights reserved.