(-)-(1R,2S)-2-Phenyl-1-<(2-phenylethynyl)oxy>cyclohexane

• 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: (-)-(1R,2S)-2-Phenyl-1-<(2-phenylethynyl)oxy>cyclohexane
• 英文别名: (-)-(1R,2S)-2-Phenyl-1-[(2-phenylethynyl)oxy]cyclohexane；2-[(1R,2S)-2-phenylcyclohexyl]oxyethynylbenzene
• 化学式: C₂₀H₂₀O
• 分子量: 276.378
• InChiKey: HVDDSEFBXHZGPO-VQTJNVASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (-)-(1R,2S)-2-Phenyl-1-<(2-phenylethynyl)oxy>cyclohexane 生成 (-)-(1R,2S)-2-Phenyl-1-<((Z)-2-phenylethenyl)oxy>cyclohexane
  参考文献：
  名称：

  Denmark Scott E., Marcin Lawrence R., J. Org. Chem, 60 (1995) N 10, S 3221-3235

  摘要：

  DOI：
• 作为产物：
  描述：

  2-氯乙炔基苯 、 (1R,2S)-trans-2-phenylcyclohexanol 在 potassium hydride 作用下， 以 四氢呋喃 为溶剂， 以75%的产率得到(-)-(1R,2S)-2-Phenyl-1-<(2-phenylethynyl)oxy>cyclohexane
  参考文献：
  名称：

  Asymmetric Nitroalkene [4 + 2] Cycloadditions: Enantioselective Synthesis of 3-Substituted and 3,4-Disubstituted Pyrrolidines

  摘要：

  2-Substituted 1-nitroalkenes undergo highly diastereoselective, Lewis-acid-promoted, [4 + 2] cycloaddition with chiral vinyl ethers derived from (R)-2,2-diphenylcyclopentanol and (1R,2S)-2-phenylcyclohexanol to afford cyclic nitronates in high yields. The resulting nitronates were reduced with hydrogen at 160 psi in the presence of platinum oxide to afford enantiomerically enriched pyrrolidines (both as the free base and N-protected derivatives) in good yields. A series of 3-substituted pyrrolidines (71-97% ee) were prepared, as well as (3S,4R)-4-methyl-3-phenyl-N-(p-tolylsulfonyl)pyrrolidine (92% ee) and (3S,4S)-3,4-diphenylpyrrolidine (99% ee). The chiral auxiliaries can be recovered in nearly quantitative yields after hydrogenation.

  DOI：

  10.1021/jo00115a043

文献信息

• Denmark Scott E., Marcin Lawrence R., J. Org. Chem, 60 (1995) N 10, S 3221-3235
  作者：Denmark Scott E., Marcin Lawrence R.

  DOI：——

  日期：——
• Asymmetric Nitroalkene [4 + 2] Cycloadditions: Enantioselective Synthesis of 3-Substituted and 3,4-Disubstituted Pyrrolidines
  作者：Scott E. Denmark、Lawrence R. Marcin

  DOI：10.1021/jo00115a043

  日期：1995.5

  2-Substituted 1-nitroalkenes undergo highly diastereoselective, Lewis-acid-promoted, [4 + 2] cycloaddition with chiral vinyl ethers derived from (R)-2,2-diphenylcyclopentanol and (1R,2S)-2-phenylcyclohexanol to afford cyclic nitronates in high yields. The resulting nitronates were reduced with hydrogen at 160 psi in the presence of platinum oxide to afford enantiomerically enriched pyrrolidines (both as the free base and N-protected derivatives) in good yields. A series of 3-substituted pyrrolidines (71-97% ee) were prepared, as well as (3S,4R)-4-methyl-3-phenyl-N-(p-tolylsulfonyl)pyrrolidine (92% ee) and (3S,4S)-3,4-diphenylpyrrolidine (99% ee). The chiral auxiliaries can be recovered in nearly quantitative yields after hydrogenation.