(1S,2R,3S,4R)-1,7,7-trimethyl-4'-methylene-N-phenyl-dihydro-3'H-spiro[bicyclo[2.2.1]heptane-2,2'-furan]-3-amine | 960216-96-0

• 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,2R,3S,4R)-1,7,7-trimethyl-4'-methylene-N-phenyl-dihydro-3'H-spiro[bicyclo[2.2.1]heptane-2,2'-furan]-3-amine
• 英文别名: (1R,2S,3R,4S)-4,7,7-trimethyl-4'-methylidene-N-phenylspiro[bicyclo[2.2.1]heptane-3,2'-oxolane]-2-amine
• CAS: 960216-96-0
• 化学式: C₂₀H₂₇NO
• 分子量: 297.44
• InChiKey: ZKRDPYCBFHEBLE-ZULIPRJHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  21.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1S,2R,3S,4R)-1,7,7-trimethyl-4'-methylene-N-phenyl-dihydro-3'H-spiro[bicyclo[2.2.1]heptane-2,2'-furan]-3-amine 、 3,6-二-2-吡啶基-1,2,4,5-四嗪 以 甲苯 为溶剂， 反应 30.0h， 以45%的产率得到(6R,9R,10S,11R,14S)-10-anilino-1,4-bis(pyridin-2-yl)-11:14-isopropylidene-14-methyl-2,3-diaza-8-oxadispiro[5.1.5.2]pentadeca-1,4-diene
  参考文献：
  名称：

  Stereoselective [4+2] cycloadditions of tetrazines to 3-oxo- and 3-arylimino-4′-methylenedihydro-3′H-spiro[bicyclo[2.2.1]heptane-2,2′-furans]

  摘要：

  Stereo selective inverse-demand [4+2] cycloadditions of 3,6-bis(pyridin-2-yl)-1,2,4,5-tetrazine and dimethyl 1,2,4,5-tetrazine3,6-dicarboxylate to 4'-methylenedihydro-3'H-spiro[bicyclo[2.2.1]heptane-2,2'-furans] and 4'-methylene-1'-(4-nitrophenyl)spiro[bicyclo(2.2.1]heptane-3,2'-pyrrolidine] were studied. Cycloadditions took place stereoselectively at the exocyclic C=C double bonds to give novel 11: 14-isopropylidene-14-methyl-2,3-diaza-8-oxadi spi to [5.1.5.2]pentadecane and 11: 14-isopropylidene-11-methyl-2,3,8-triazadispiro[5.1.5.2]pentadecane derivatives in 50-98% de. The structures of the novel dispiro compounds were determined by NMR techniques, NOESY spectroscopy and X-ray diffraction. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.11.012
• 作为产物：
  描述：

  (1S,4R)-1,7,7-trimethyl-3-(phenylimino)bicyclo[2.2.1]heptan-2-one 在 palladium diacetate lithium aluminium tetrahydride 、 三异丙基亚磷酸酯 作用下， 以 四氢呋喃 、 乙醚 、 甲苯 为溶剂， 反应 3.0h， 生成 (1S,2R,3S,4R)-1,7,7-trimethyl-4'-methylene-N-phenyl-dihydro-3'H-spiro[bicyclo[2.2.1]heptane-2,2'-furan]-3-amine
  参考文献：
  名称：

  经由三亚甲基甲烷向（1 S，3 EZ，4 R）-3-arylimino-1,7,7-的立体选择性环加成反应合成螺[bicyclo [2.2.1]庚烷-2,2'-呋喃] -3-胺三甲基双环[2.2.1]庚烷-2-酮

  摘要：

  三亚甲基甲烷（TMM）的立体选择性[3 + 2]环加成与（1 S，3 EZ，4 R）-3-芳基-1,7,7-三甲基双环[2.2.1]庚烷-的环外CO和CN双键2-one给出了相应的螺[双环[2.2.1]庚烷-2,2'-呋喃]和螺[双环[2.2.1]庚烷-3,2'-吡咯烷]衍生物。这些环加合物中CN或CO键的进一步立体选择性还原提供了新的手性胺，二胺和新的氨基醇。的CN双键的所有环加成和减少发生在从较少受阻内的（1 -面小号，3 EZ，4 - [R）-3-芳基氨基-1,7,7-三甲基双环[2.2.1]庚基-2-酮，因此以100％的de给出相应的产物。通过NMR，NOESY光谱和通过X射线衍射确定结构。

  DOI：

  10.1016/j.tetasy.2007.09.018

文献信息

• Stereoselective [4+2] cycloadditions of tetrazines to 3-oxo- and 3-arylimino-4′-methylenedihydro-3′H-spiro[bicyclo[2.2.1]heptane-2,2′-furans]
  作者：Uroš Grošelj、Anton Meden、Branko Stanovnik、Jurij Svete

  DOI：10.1016/j.tetasy.2007.11.012

  日期：2007.11

  Stereo selective inverse-demand [4+2] cycloadditions of 3,6-bis(pyridin-2-yl)-1,2,4,5-tetrazine and dimethyl 1,2,4,5-tetrazine3,6-dicarboxylate to 4'-methylenedihydro-3'H-spiro[bicyclo[2.2.1]heptane-2,2'-furans] and 4'-methylene-1'-(4-nitrophenyl)spiro[bicyclo(2.2.1]heptane-3,2'-pyrrolidine] were studied. Cycloadditions took place stereoselectively at the exocyclic C=C double bonds to give novel 11: 14-isopropylidene-14-methyl-2,3-diaza-8-oxadi spi to [5.1.5.2]pentadecane and 11: 14-isopropylidene-11-methyl-2,3,8-triazadispiro[5.1.5.2]pentadecane derivatives in 50-98% de. The structures of the novel dispiro compounds were determined by NMR techniques, NOESY spectroscopy and X-ray diffraction. (c) 2007 Elsevier Ltd. All rights reserved.
• Synthesis of spiro[bicyclo[2.2.1]heptane-2,2′-furan]-3-amines via stereoselective cycloadditions of trimethylenemethane to (1S,3EZ,4R)-3-arylimino-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ones
  作者：Uroš Grošelj、Anton Meden、Branko Stanovnik、Jurij Svete

  DOI：10.1016/j.tetasy.2007.09.018

  日期：2007.9

  7,7-trimethylbicyclo[2.2.1]heptan-2-ones gave the corresponding spiro[bicyclo[2.2.1]heptane-2,2′-furan] and spiro[bicyclo[2.2.1]heptane-3,2′-pyrrolidine] derivatives. Further stereoselective reductions of the CN or CO bond in these cycloadducts furnished new chiral amines, diamines, and a new aminoalcohol. All cycloadditions and reductions of the CN double bonds took place from the less hindered endo-face

  三亚甲基甲烷（TMM）的立体选择性[3 + 2]环加成与（1 S，3 EZ，4 R）-3-芳基-1,7,7-三甲基双环[2.2.1]庚烷-的环外CO和CN双键2-one给出了相应的螺[双环[2.2.1]庚烷-2,2'-呋喃]和螺[双环[2.2.1]庚烷-3,2'-吡咯烷]衍生物。这些环加合物中CN或CO键的进一步立体选择性还原提供了新的手性胺，二胺和新的氨基醇。的CN双键的所有环加成和减少发生在从较少受阻内的（1 -面小号，3 EZ，4 - [R）-3-芳基氨基-1,7,7-三甲基双环[2.2.1]庚基-2-酮，因此以100％的de给出相应的产物。通过NMR，NOESY光谱和通过X射线衍射确定结构。