(+)-2,2-diphenylcyclopentanol | 151715-90-1

• 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: (+)-2,2-diphenylcyclopentanol
• 英文别名: (1S)-2,2-diphenylcyclopentan-1-ol
• CAS: 151715-90-1
• 化学式: C₁₇H₁₈O
• 分子量: 238.329
• InChiKey: TYFASEURNPWTII-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (+)-2,2-diphenylcyclopentanol 在 吡啶 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 (S)-2,2-diphenyl-1-cyclopentyl 2-oxohexanoate
  参考文献：
  名称：

  草酸酯对格氏试剂的不对称合成手性α-酮酯

  摘要：

  在进行含氯代谢物（-）-隐孢子菌素的不对称合成的过程中，需要有效且可靠的手性α-酮酸酯的不对称合成。通过在40°C于四氢呋喃中的对称或混合草酸盐形式的格氏添加剂，可以方便地以51-84％的产率生成这些化合物。该反应与脂肪族或芳香族格氏试剂同样有效。

  DOI：

  10.1016/j.tetasy.2003.08.013
• 作为产物：
  描述：

  (2S,3aR,3R,6R)-hexahydro-6-[(1S)-2,2-diphenylcyclopentyloxy]isoxazolo[2,3-b][1,2]oxazine-2,3-dicarboxylic acid dimethyl ester 在 Raney nickel W-2 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、1.24 MPa 条件下， 反应 48.0h， 以55%的产率得到[1S,2S,7aR]-hexahydro-2-hydroxy-3-oxo-1H-pyrrolizine-1-carboxylic acid methyl ester
  参考文献：
  名称：

  Tandem [4 + 2]/[3 + 2] Cycloadditions with Nitroethylene

  摘要：

  The simplest nitroalkene, nitroethylene, undergoes Lewis acid-promoted [4 + 2] cycloaddition with chiral vinyl ethers to afford cyclic nitronates with high diastereoselectivity. The resulting cyclic nitronates react with electron deficient alkenes to effect a face selective [3 + 2] cycloaddition. The origin of stereocontrol in the [3 + 2] cycloaddition is due to the single ring substituent, a remote acetal center. The scope and limitations of the use of nitroethylene as a 4 pi component in Lewis acid-promoted cycloadditions are documented and discussed. Additionally, concise syntheses of the pyrrolizidine alkaloids (+)-macronecine and (+)-petasinecine are presented.

  DOI：

  10.1021/jo972280f

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.