1,3-bis[((S)-1-phenylethyl)]-4(R),5(R),6(S),9(R)-6,9-diethyl-2,3,4,5,6,9-hexahydro-1,3-diazaindene

• 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: 1,3-bis[((S)-1-phenylethyl)]-4(R),5(R),6(S),9(R)-6,9-diethyl-2,3,4,5,6,9-hexahydro-1,3-diazaindene
• 英文别名: (3aR,4S,7R,7aR)-4,7-bis(ethenyl)-1,3-bis[(1S)-1-phenylethyl]-3a,4,7,7a-tetrahydro-2H-benzimidazole
• 化学式: C₂₇H₃₂N₂
• 分子量: 384.564
• InChiKey: BBNGAFLGGDJUJC-RYGRLOLMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  6.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (4R,5R)-N,N'-bis[(1S)-1-phenylethyl]-3,6-divinyl-1,7-octadiene-4,5-diamine 在 Grubbs catalyst first generation magnesium sulfate 、 对甲苯磺酸 、 三氟乙酸 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 77.0h， 生成 1,3-bis[((S)-1-phenylethyl)]-4(R),5(R),6(S),9(R)-6,9-diethyl-2,3,4,5,6,9-hexahydro-1,3-diazaindene
  参考文献：
  名称：

  Progress towards the Stereoselective Synthesis of 3,6-Disubstituted 1,2-Diamino-4-cyclohexenes by Ring Closing Metathesis Reaction

  摘要：

  The ring closing metathesis of 4(R),5(R)-bis[1(S)-phenylethylamino]-3,6-diethenyl-1,7-octadiene required the preliminary formation of the cyclic formaldehyde aminal, then the use of the Grubbs, ruthenium benzylidene complex (10 mol %) in refluxing toluene in the presence of 2 equivalents of trifluoroacetic acid. The cyclic aminal was cleaved in situ after the cyclisation step, so that the final product was the 1,2-diamino-3,6-diethenylcyclohex-4-ene derivative. The predominant C-1-symmetric diastereomer was isolated with 48% yield.

  DOI：

  10.1002/1615-4169(200212)344:10<1068::aid-adsc1068>3.0.co;2-s

文献信息

• Progress towards the Stereoselective Synthesis of 3,6-Disubstituted 1,2-Diamino-4-cyclohexenes by Ring Closing Metathesis Reaction
  作者：Stefano Grilli、Gianluca Martelli、Diego Savoia、Carla Zazzetta

  DOI：10.1002/1615-4169(200212)344:10<1068::aid-adsc1068>3.0.co;2-s

  日期：2002.12

  The ring closing metathesis of 4(R),5(R)-bis[1(S)-phenylethylamino]-3,6-diethenyl-1,7-octadiene required the preliminary formation of the cyclic formaldehyde aminal, then the use of the Grubbs, ruthenium benzylidene complex (10 mol %) in refluxing toluene in the presence of 2 equivalents of trifluoroacetic acid. The cyclic aminal was cleaved in situ after the cyclisation step, so that the final product was the 1,2-diamino-3,6-diethenylcyclohex-4-ene derivative. The predominant C-1-symmetric diastereomer was isolated with 48% yield.