N1-{(1S,2R,3S,4R)-1,7,7-trimethyl-4'-methylenedihydro-3'H-spiro[bicyclo[2.2.1]heptane-2,2'-furan]-3-yl}-N2-{(1S,2R,3E,4R)-1,7,7-trimethyl-4'-methylenedihydro-3'H-spiro[bicyclo[2.2.1]heptane-2,2'-furan]-3-ylidene}benzene-1,2-diamine | 1016546-18-1

• 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: N1-{(1S,2R,3S,4R)-1,7,7-trimethyl-4'-methylenedihydro-3'H-spiro[bicyclo[2.2.1]heptane-2,2'-furan]-3-yl}-N2-{(1S,2R,3E,4R)-1,7,7-trimethyl-4'-methylenedihydro-3'H-spiro[bicyclo[2.2.1]heptane-2,2'-furan]-3-ylidene}benzene-1,2-diamine
• 英文别名: N¹-{(1S,2R,3S,4R)-1,7,7-trimethyl-4'-methylenedihydro-3'H-spiro[bicyclo[2.2.1]heptane-2,2'-furan]-3-yl}-N²-{(1S,2R,3E,4R)-1,7,7-trimethyl-4'-methylenedihydro-3'H-spiro[bicyclo[2.2.1]heptane-2,2'-furan]-3-ylidene}benzene-1,2-diamine
• CAS: 1016546-18-1
• 化学式: C₃₄H₄₆N₂O₂
• 分子量: 514.751
• InChiKey: IBJAMLKCXVLNTC-FKEASLMXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.88
• 重原子数：
  38.0
• 可旋转键数：
  3.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  42.85
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  N1-{(1S,2R,3S,4R)-1,7,7-trimethyl-4'-methylenedihydro-3'H-spiro[bicyclo[2.2.1]heptane-2,2'-furan]-3-yl}-N2-{(1S,2R,3E,4R)-1,7,7-trimethyl-4'-methylenedihydro-3'H-spiro[bicyclo[2.2.1]heptane-2,2'-furan]-3-ylidene}benzene-1,2-diamine 在 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 20.0h， 以88%的产率得到N¹,N²-bis{(1S,2R,3S,4R)-1,7,7-trimethyl-4'-methylenedihydro-3'H-spiro[bicyclo[2.2.1]heptane-2,2'-furan]-3-yl}benzene-1,2-diamine
  参考文献：
  名称：

  Synthesis of novel C2-symmetric 1,3-bis{(1S,2R,3S,4R)-1,7,7-trimethyl-3′H-spiro[bicyclo[2.2.1]heptane-2,2′-furan]-3-yl}benzoimidazolium tetrafluoroborates

  摘要：

  Two new C-2-symmetric benzoimidazolium tetrafluoroborates 19 and 20 were prepared from (1S)-(+)-camphorquinone 1 in seven and eight steps, respectively. Thus, N-1-((1S,2R,3S,4R)-1,7,7-trimethyl-4'-methylenedihydro-3'H-spiro[bicyclo[2.2.1]heptane-2,2'-furan]-3-yl)benzene-1.2-diamine 11, available in three steps from 1, was first condensed with 1 to afford amino imines 12 and 13/13'. [3 + 2] Cycloaddition of trimethylenemethane (TMM) to 12 or 13/13' gave cycloadduct 17, which was successfully reduced to diamine 4 using NaCNBH3. Catalytic hydrogenation of methylene groups of 4 gave the methyl analogue 18. Finally, cyclization of diamines 4 and 18 with triethyl orthoformate furnished the desired C-2-symmetric benzoimidazolium tetrafluoroborates 19 and 20, respectively. The structures were determined by NMR techniques, NOESY spectroscopy, and X-ray diffraction. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.01.005
• 作为产物：
  描述：

  N1-[(1S,3E,4R)-2-oxo-1,7,7-trimethylbicyclo[2.2.1]hept-3-ylidene]-N2-{(1S,2R,3S,4R)-1,7,7-trimethyl-4'-methylenedihydro-3'H-spiro[bicyclo[2.2.1]heptane-2,2'-furan]-3-yl}benzene-1,2-diamine 、 2-(三甲基硅甲基)烯丙基乙酸酯 在 palladium diacetate 三异丙基亚磷酸酯 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 3.0h， 以69%的产率得到N1-{(1S,2R,3S,4R)-1,7,7-trimethyl-4'-methylenedihydro-3'H-spiro[bicyclo[2.2.1]heptane-2,2'-furan]-3-yl}-N2-{(1S,2R,3E,4R)-1,7,7-trimethyl-4'-methylenedihydro-3'H-spiro[bicyclo[2.2.1]heptane-2,2'-furan]-3-ylidene}benzene-1,2-diamine
  参考文献：
  名称：

  Synthesis of novel C2-symmetric 1,3-bis{(1S,2R,3S,4R)-1,7,7-trimethyl-3′H-spiro[bicyclo[2.2.1]heptane-2,2′-furan]-3-yl}benzoimidazolium tetrafluoroborates

  摘要：

  Two new C-2-symmetric benzoimidazolium tetrafluoroborates 19 and 20 were prepared from (1S)-(+)-camphorquinone 1 in seven and eight steps, respectively. Thus, N-1-((1S,2R,3S,4R)-1,7,7-trimethyl-4'-methylenedihydro-3'H-spiro[bicyclo[2.2.1]heptane-2,2'-furan]-3-yl)benzene-1.2-diamine 11, available in three steps from 1, was first condensed with 1 to afford amino imines 12 and 13/13'. [3 + 2] Cycloaddition of trimethylenemethane (TMM) to 12 or 13/13' gave cycloadduct 17, which was successfully reduced to diamine 4 using NaCNBH3. Catalytic hydrogenation of methylene groups of 4 gave the methyl analogue 18. Finally, cyclization of diamines 4 and 18 with triethyl orthoformate furnished the desired C-2-symmetric benzoimidazolium tetrafluoroborates 19 and 20, respectively. The structures were determined by NMR techniques, NOESY spectroscopy, and X-ray diffraction. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.01.005