(1S,2S)-2-Furan-2-yl-cyclopropanecarboxylic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester | 196609-10-6

• 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,2S)-2-Furan-2-yl-cyclopropanecarboxylic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester
• 英文别名: [(1R,2S,5R)-5-methyl-2-(2-phenylpropan-2-yl)cyclohexyl] (1S,2S)-2-(furan-2-yl)cyclopropane-1-carboxylate
• CAS: 196609-10-6
• 化学式: C₂₄H₃₀O₃
• 分子量: 366.5
• InChiKey: YYWFHDKSPWRNLC-XJESJRCUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  39.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1S,2S)-2-Furan-2-yl-cyclopropanecarboxylic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 14.0h， 以76%的产率得到(+)-(1S,2S)-2-(furan-2-yl)cyclopropylmethanol
  参考文献：
  名称：

  High-Diastereoselective and Enantioselective Cyclopropanation of α,β-Unsaturated Fischer Carbene Complexes:  Synthesis of Chiral 1,2-Disubstituted and 1,2,3-Trisubstituted Cyclopropanes

  摘要：

  Reaction of chiral vinylcarbene complexes 1 with in situ-generated iodomethyllithium or dibromomethyllithium gives cyclopropylcarbene complexes 4 and 13, respectively, with high diastereoselectivity (de > 91%). Different enantiopure 1,2-disubstituted and 1,2,3-trisubstituted cyclopropanes are obtained starting from chiral carbene complexes 4 and 13, respectively.

  DOI：

  10.1021/jo9708708
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 吡啶-N-氧化物 作用下， 以 四氢呋喃 为溶剂， 反应 14.0h， 生成 (1S,2S)-2-Furan-2-yl-cyclopropanecarboxylic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester
  参考文献：
  名称：

  High-Diastereoselective and Enantioselective Cyclopropanation of α,β-Unsaturated Fischer Carbene Complexes:  Synthesis of Chiral 1,2-Disubstituted and 1,2,3-Trisubstituted Cyclopropanes

  摘要：

  Reaction of chiral vinylcarbene complexes 1 with in situ-generated iodomethyllithium or dibromomethyllithium gives cyclopropylcarbene complexes 4 and 13, respectively, with high diastereoselectivity (de > 91%). Different enantiopure 1,2-disubstituted and 1,2,3-trisubstituted cyclopropanes are obtained starting from chiral carbene complexes 4 and 13, respectively.

  DOI：

  10.1021/jo9708708

文献信息

• High-Diastereoselective and Enantioselective Cyclopropanation of α,β-Unsaturated Fischer Carbene Complexes:  Synthesis of Chiral 1,2-Disubstituted and 1,2,3-Trisubstituted Cyclopropanes
  作者：José Barluenga、Pablo L. Bernad、José M. Concellón、Alejandro Piñera-Nicolás and、Santiago García-Granda

  DOI：10.1021/jo9708708

  日期：1997.10.1

  Reaction of chiral vinylcarbene complexes 1 with in situ-generated iodomethyllithium or dibromomethyllithium gives cyclopropylcarbene complexes 4 and 13, respectively, with high diastereoselectivity (de > 91%). Different enantiopure 1,2-disubstituted and 1,2,3-trisubstituted cyclopropanes are obtained starting from chiral carbene complexes 4 and 13, respectively.