2α,3β,4α,5β-tetramethylcyclopentanone

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2α,3β,4α,5β-tetramethylcyclopentanone
• 英文别名: (2R,3S,4S,5R)-2,3,4,5-tetramethylcyclopentan-1-one
• 化学式: C₉H₁₆O
• 分子量: 140.225
• InChiKey: CMLJQZJBJPNNFR-RULNZFCNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.11
• 重原子数：
  10.0
• 可旋转键数：
  0.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  2α,3β,4α,5β-tetramethylcyclopentanone 在 lithium aluminium tetrahydride 作用下， 生成 (2R,3S,4S,5R)-2,3,4,5-Tetramethyl-cyclopentanol
  参考文献：
  名称：

  Optical resolution of alltrans-2,3,4,5-tetramethylcyclo-pentanone and determination of the configuration of the laevorotatory enantiomer

  摘要：

  alltrans-2,3,4,5-Tetramethylcyclopentanone 4 is reduced to the corresponding alcohol 5. The optical resolution of 5 was carried out by using the phthalate halfester method. The configuration of (-)-4 is determined by CD. The possibility of the application as a chiral auxiliary is demonstrated.

  DOI：

  10.1016/s0957-4166(00)86140-6
• 作为产物：
  描述：

  2,3,4,5-四甲基-2-环戊烯酮 在 lithium aluminium tetrahydride 、 sodium dichromate 、 氨 、 lithium 作用下， 以 乙醚 、 水 为溶剂， 生成 2α,3β,4α,5β-tetramethylcyclopentanone
  参考文献：
  名称：

  Optical resolution of alltrans-2,3,4,5-tetramethylcyclo-pentanone and determination of the configuration of the laevorotatory enantiomer

  摘要：

  alltrans-2,3,4,5-Tetramethylcyclopentanone 4 is reduced to the corresponding alcohol 5. The optical resolution of 5 was carried out by using the phthalate halfester method. The configuration of (-)-4 is determined by CD. The possibility of the application as a chiral auxiliary is demonstrated.

  DOI：

  10.1016/s0957-4166(00)86140-6

文献信息

• A study of the stereochemical factors involved in multistep 1,2-hydride transfers
  作者：Ted S. Sorensen、Steven M. Whitworth

  DOI：10.1021/ja00174a029

  日期：1990.8

  all-trans-1,2,3,4,5-pentamethylcyclopentyl cation have been developed. These cations both undergo very rapid multiple 1,2-hydride shifts, but the rate of this process is about 40 times faster in the all-trans case. This implies that the stereochemistry of the penultimate hydride in the rearrangement cascade can affect the rate of a given 1,2-hydride shift, i.e. that it is better if this penultimate

  已经开发了合成全（顺式和全反式 1,2,3,4,5-五甲基环戊基阳离子。这些阳离子都经历了非常快速的多次 1,2-氢化物转移，但该过程的速率在全反式情况下大约快 40 倍。这意味着重排级联中倒数第二个氢化物的立体化学会影响给定的 1,2-氢化物移位的速率，即如果这个倒数第二个氢化物位于转移到迁移中。这项工作的另一个含义是母体环戊基阳离子中的氢化物转移可能是部分有序的，并且通常快速的多次氢化物转移可能受到相同的标准
• SORENSEN, TED S.;WHITWORTH, STEVEN M., J. AMER. CHEM. SOC. , 112,(1990) N8, C. 6647-6651
  作者：SORENSEN, TED S.、WHITWORTH, STEVEN M.

  DOI：——

  日期：——
• Optical resolution of alltrans-2,3,4,5-tetramethylcyclo-pentanone and determination of the configuration of the laevorotatory enantiomer
  作者：Norbert Hoffmann、Hans-Dieter Scharf

  DOI：10.1016/s0957-4166(00)86140-6

  日期：1991.1

  alltrans-2,3,4,5-Tetramethylcyclopentanone 4 is reduced to the corresponding alcohol 5. The optical resolution of 5 was carried out by using the phthalate halfester method. The configuration of (-)-4 is determined by CD. The possibility of the application as a chiral auxiliary is demonstrated.