(R)-2,2-Diphenyl-1-(1(Z)-propenyloxy)cyclopentane | 164731-32-2

• 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: (R)-2,2-Diphenyl-1-(1(Z)-propenyloxy)cyclopentane
• 英文别名: [(2R)-1-phenyl-2-[(Z)-prop-1-enoxy]cyclopentyl]benzene
• CAS: 164731-32-2
• 化学式: C₂₀H₂₂O
• 分子量: 278.394
• InChiKey: OJSKMPGSCYMTPN-WPYPGRIHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 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：

  (2E,6E)-methyl 7-nitro-2,6-octadienoate 、 (R)-2,2-Diphenyl-1-(1(Z)-propenyloxy)cyclopentane 在 二异丙氧基二氯化钛 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以95%的产率得到6-<(R)-2,2-Diphenylcyclopentoxy>octahydro-5,7b-dimethyl-1,7-dioxa-7a-azacyclopentindene-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Nitroalkene Inter [4 + 2]/Intra [3 + 2] Tandem Cycloadditions. 7. Application of (R)-(-)-2,2-Diphenylcyclopentanol as the Chiral Auxiliary

  摘要：

  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.

  DOI：

  10.1021/jo00115a042
• 作为产物：
  描述：

  3-((R)-2,2-Diphenylcyclopentoxy)-1-propene 在 RhCl(PPh₃)3 三乙烯二胺 作用下， 以 乙醇 为溶剂， 反应 9.0h， 生成 (R)-2,2-Diphenyl-1-(1(Z)-propenyloxy)cyclopentane 、 (R)-2,2-Diphenyl-1-(1(E)-propenyloxy)cyclopentane
  参考文献：
  名称：

  Nitroalkene Inter [4 + 2]/Intra [3 + 2] Tandem Cycloadditions. 7. Application of (R)-(-)-2,2-Diphenylcyclopentanol as the Chiral Auxiliary

  摘要：

  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.

  DOI：

  10.1021/jo00115a042

文献信息

• 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.
• 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.