(S)-3-Pentyl-cyclopentanone | 102776-41-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-3-Pentyl-cyclopentanone
• 英文别名: (3S)-3-pentylcyclopentan-1-one
• CAS: 102776-41-0
• 化学式: C₁₀H₁₈O
• 分子量: 154.252
• InChiKey: GWSPTFQZKGLWES-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (S)-3-Pentyl-cyclopentanone 在 1,4-dihydronicotinamide adenine dinucleotide 、 horse liver alcohol dehydrogenase 作用下， 以 异丙醇 为溶剂， 生成 (1R,3R)-3-Pentyl-cyclopentanol 、 (1S,3R)-3-Pentyl-cyclopentanol
  参考文献：
  名称：

  Use of shift reagent with MTPA derivatives in19F NMR spectrocopy: IV—Determination of enantiomeric composition for a variety of secondary cycloalkanols. A survey

  摘要：

  AbstractChiral secondary cycloalkanols (monocyclic alcohols) are derivatized to the corresponding (R)‐α‐methoxy‐α‐trifluoromethyl‐α‐phenylacetic acid [(R)‐MTPA] esters and analysed by 19F NMR in the presence of tris(6,6,7,7,8,8,8‐heptafluoro‐2,2‐dimethyl‐3,5‐octanedionato) europium(III) [Eu(fod)3]. Using this method the enantiomeric composition can be measured for several cyclopentanols, cyclohexanols and cycloheptanols, with a variety of substitution patterns. It is shown that a mixture of four stereoisomeric cycloalkanols, such as cis and trans disubstituted alcohols, can be analysed simultaneously.

  DOI：

  10.1002/omr.1270210609
• 作为产物：
  描述：

  (R)-2-Chloro-4-pentyl-cyclopent-2-enone 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 以80%的产率得到(S)-3-Pentyl-cyclopentanone
  参考文献：
  名称：

  二氯乙烯酮与手性烯醇醚的环加成反应中的不对称诱导。光学活性环戊烯酮衍生物的通用方法。

  摘要：

  在二氯乙烯与手性烯醇醚的环加成反应中观察到明显的不对称诱导。所得非对映体环丁酮已被转化为旋光形式的合成上有用的α-氯环戊烯酮。

  DOI：

  10.1016/s0040-4039(01)80878-9

文献信息

• GREENE, A. E.;CARBONNIER, F., TETRAHEDRON LETT., 1985, 26, N 45, 5525-5528
  作者：GREENE, A. E.、CARBONNIER, F.

  DOI：——

  日期：——
• Asymmetric induction in the cycloaddition reaction of dichloroketene with chiral enol ethers. A versatile approach to optically active cyclopentenone derivatives.
  作者：Andrew E. Greene、Florence Charbonnier

  DOI：10.1016/s0040-4039(01)80878-9

  日期：1985.1

  Significant asymmetric induction has been observed in the cycloaddition reaction of dichloroketene with chiral enol ethers. The resultant diastereomeric cyclobutanones have been converted to synthetically useful α-chlorocyclopentenones in optically active form.

  在二氯乙烯与手性烯醇醚的环加成反应中观察到明显的不对称诱导。所得非对映体环丁酮已被转化为旋光形式的合成上有用的α-氯环戊烯酮。
• Use of shift reagent with MTPA derivatives in19F NMR spectrocopy: IV—Determination of enantiomeric composition for a variety of secondary cycloalkanols. A survey
  作者：E. M. Merckx、J. A. Lepoivre、G. L. Lemière、F. C. Alderweireldt

  DOI：10.1002/omr.1270210609

  日期：1983.6

  AbstractChiral secondary cycloalkanols (monocyclic alcohols) are derivatized to the corresponding (R)‐α‐methoxy‐α‐trifluoromethyl‐α‐phenylacetic acid [(R)‐MTPA] esters and analysed by 19F NMR in the presence of tris(6,6,7,7,8,8,8‐heptafluoro‐2,2‐dimethyl‐3,5‐octanedionato) europium(III) [Eu(fod)3]. Using this method the enantiomeric composition can be measured for several cyclopentanols, cyclohexanols and cycloheptanols, with a variety of substitution patterns. It is shown that a mixture of four stereoisomeric cycloalkanols, such as cis and trans disubstituted alcohols, can be analysed simultaneously.