(1S,3S,4S,6R)-3,7,7-trimethylbicyclo[4.1.0]heptane-3,4-diamine | 1310549-32-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1S,3S,4S,6R)-3,7,7-trimethylbicyclo[4.1.0]heptane-3,4-diamine
• CAS: 1310549-32-6
• 化学式: C₁₀H₂₀N₂
• 分子量: 168.282
• InChiKey: KGDDYCGZGJQMBA-VEVYYDQMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  52
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3,8,8-三甲基-4-氧杂三环[5.1.0.03,5]辛烷 在 lithium aluminium tetrahydride 、 sodium azide 、 cerium(III) chloride heptahydrate 、 氯化铵 、 三苯基膦 作用下， 以 1,4-二氧六环 、 甲醇 、 甲基叔丁基醚 、 水 、 乙腈 为溶剂， 反应 39.92h， 生成 (1S,3S,4S,6R)-3,7,7-trimethylbicyclo[4.1.0]heptane-3,4-diamine
  参考文献：
  名称：

  Synthesis of new enantiopure trans-3,4-diaminocaranes from (+)-3-carene

  摘要：

  A synthetic strategy to obtain new enantiopure trans-3,4-diaminocaranes derived from (+)-3-carene via a stereoselective methodology is described. The stereoselective preparation of 3,4-alpha-carene- or 3,4-beta-carene-epoxide is followed by a ring opening by sodium azide to obtain the azido-alcohols. Subsequent cyclization affords the corresponding aziridine diastereoisomers, which are converted to azido amines by opening of the aziridine rings by sodium azide and then reduced to the final diamine diastereoisomers. The absolute configurations of the final diamines and of novel intermediates are established by H-1 NMR spectra correlated with conformational analysis supported by molecular modeling. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.02.027

文献信息

• Synthesis of new enantiopure trans-3,4-diaminocaranes from (+)-3-carene
  作者：Cristina Cimarelli、Davide Fratoni、Gianni Palmieri

  DOI：10.1016/j.tetasy.2011.02.027

  日期：2011.3

  A synthetic strategy to obtain new enantiopure trans-3,4-diaminocaranes derived from (+)-3-carene via a stereoselective methodology is described. The stereoselective preparation of 3,4-alpha-carene- or 3,4-beta-carene-epoxide is followed by a ring opening by sodium azide to obtain the azido-alcohols. Subsequent cyclization affords the corresponding aziridine diastereoisomers, which are converted to azido amines by opening of the aziridine rings by sodium azide and then reduced to the final diamine diastereoisomers. The absolute configurations of the final diamines and of novel intermediates are established by H-1 NMR spectra correlated with conformational analysis supported by molecular modeling. (C) 2011 Elsevier Ltd. All rights reserved.