3-((R)-2,2-Diphenylcyclopentoxy)-1-propene | 156908-40-6

• 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: 3-((R)-2,2-Diphenylcyclopentoxy)-1-propene
• 英文别名: [(2R)-1-phenyl-2-prop-2-enoxycyclopentyl]benzene
• CAS: 156908-40-6
• 化学式: C₂₀H₂₂O
• 分子量: 278.394
• InChiKey: WFROHNCVTOLBIU-LJQANCHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  21
• 可旋转键数：
  5
• 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：

  3-((R)-2,2-Diphenylcyclopentoxy)-1-propene 以74%的产率得到
  参考文献：
  名称：

  Denmark Scott E., Schnute Mark E., J. Org. Chem, 59 (1994) N 16, S 4576-4595

  摘要：

  DOI：
• 作为产物：
  描述：

  (R)-(-)-2,2-diphenylcyclopentanol 、 3-溴丙烯 在 potassium hydride 作用下， 以 四氢呋喃 为溶剂， 以89%的产率得到3-((R)-2,2-Diphenylcyclopentoxy)-1-propene
  参考文献：
  名称：

  Nitroalkene [4 + 2] Cycloadditions with 2-(Acyloxy)vinyl Ethers. Stereoselective Synthesis of 3-Hydroxy-4-substituted-pyrrolidines

  摘要：

  2-(Acyloxy)vinyl ethers undergo regioselective [4 + 2] cycloadditions with nitroalkenes (promoted by SnCl4) to afford subsutituted 5-acetoxy nitronates in good yields (68-91%). Endo/exo selectivity in the cycloadditions has been found to be dependent on the nitroalkene substitution; 2-aryl-1-nitroalkenes provided exclusively exo cycloadducts while 2-cyclohexyl-1-nitroalkene 28 afforded predominately endo cycloadducts in a ratio of 12:1. The resulting nitronates can be elaborated to N-tosyl-4-substituted-3-hydroxypyrrolidines by hydrogenolysis (160 psi of H-2/PtO2) or to bicyclic alpha-hydroxy lactams by [3 + 2] cycloaddition followed by hydrogenation (14.7 psi of H-2/Raney nickel). A chiral 2-acetoxyvinyl ether derived from (R)-2,2-diphenylcyclopentanol has been employed in the cycloaddition-hydrogenation sequence to prepare an optically active N-tosyl-3-hydroxypyrrolidine in 96% ee.

  DOI：

  10.1021/jo00095a038

文献信息

• Nitroalkene Inter [4 + 2]/Intra [3 + 2] Tandem Cycloadditions. 7. Application of (R)-(-)-2,2-Diphenylcyclopentanol as the Chiral Auxiliary
  作者：Scott E. Denmark、Mark E. Schnute、Lawrence R. Marcin、Atli Thorarensen

  DOI：10.1021/jo00115a042

  日期：1995.5

  Chiral enol ethers derived from (R)-(-)-2,2-diphenylcyclopentanol ((-)-3) have been found to provide high levels of asymmetric induction in tandem inter [4 + 2]/intra [3 + 2] nitroalkene cycloadditions. The chiral auxiliary (>97% ee) is readily prepared in three steps from diphenylacetonitrile employing an asymmetric oxazaborolidine-catalyzed borane reduction. Either enantiomeric series of tandem cycloaddition/hydrogenolysis product 7 is available from the chiral auxiliary of a single absolute configuration by judicious selection of the Lewis acid promoter, Ti(O-i-Pr)(2)Cl-2 (98% ee, (-)-7) or MAPh (93% ee, (+)-7). Propenyl ethers derived from (-)-3 undergo endo selective [4 + 2] cycloadditions (2.3/1 - 8.2/1) in the presence Ti(O-i-Pr)(2)Cl-2; however, exo selective [4 + 2] cycloadditions (10.2/1 - 54.8/1) are observed in the presence of MAPh.
• Denmark Scott E., Schnute Mark E., J. Org. Chem, 59 (1994) N 16, S 4576-4595
  作者：Denmark Scott E., Schnute Mark E.

  DOI：——

  日期：——
• Nitroalkene [4 + 2] Cycloadditions with 2-(Acyloxy)vinyl Ethers. Stereoselective Synthesis of 3-Hydroxy-4-substituted-pyrrolidines
  作者：Scott E. Denmark、Mark E. Schnute

  DOI：10.1021/jo00095a038

  日期：1994.8

  2-(Acyloxy)vinyl ethers undergo regioselective [4 + 2] cycloadditions with nitroalkenes (promoted by SnCl4) to afford subsutituted 5-acetoxy nitronates in good yields (68-91%). Endo/exo selectivity in the cycloadditions has been found to be dependent on the nitroalkene substitution; 2-aryl-1-nitroalkenes provided exclusively exo cycloadducts while 2-cyclohexyl-1-nitroalkene 28 afforded predominately endo cycloadducts in a ratio of 12:1. The resulting nitronates can be elaborated to N-tosyl-4-substituted-3-hydroxypyrrolidines by hydrogenolysis (160 psi of H-2/PtO2) or to bicyclic alpha-hydroxy lactams by [3 + 2] cycloaddition followed by hydrogenation (14.7 psi of H-2/Raney nickel). A chiral 2-acetoxyvinyl ether derived from (R)-2,2-diphenylcyclopentanol has been employed in the cycloaddition-hydrogenation sequence to prepare an optically active N-tosyl-3-hydroxypyrrolidine in 96% ee.