(R)-2-n-hexylcyclopentanone | 214335-64-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-2-n-hexylcyclopentanone
• 英文别名: (R)-2-hexylcyclopentanone；(2R)-2-hexylcyclopentan-1-one
• CAS: 214335-64-5
• 化学式: C₁₁H₂₀O
• 分子量: 168.279
• InChiKey: JTHVYOIHZNYRCC-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 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：

  (R)-2-n-hexylcyclopentanone 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 生成 (R)-δ-undecalactone
  参考文献：
  名称：

  Synthesis and odor of optically active 2-n-hexyl- and 2-n-heptylcyclopentanone and the corresponding δ-lactones

  摘要：

  Enantiomeric 2-n-hexyl- and 2-n-heptylcyclopentanones (3) and (4) have been synthesized by asymmetric hydrogenation of 2-n-hexylidene and 2-n-heptylidenecyclopentanones (1) and (2) with Ru2Cl4[p-tolyl-binap](2)NEt3 complexes. The differences in odor qualities between enantiomeric pairs of the ketones 3 and 4 have been found to be small, and the same odor threshold values have been observed between the enantiomeric pairs, although the corresponding delta-undeca- and delta-dodecalactones (6) and (7), synthesized by Baeyer-Villiger oxidation of the chiral ketones 3 and 4, showed a fairly large difference in the threshold values between the enantiomeric pairs. (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(02)02312-2
• 作为产物：
  描述：

  正己醛 在 Ru₂Cl₄((S)-(-)-2,2'-bis(di-p-tolylphosphino)-1,1'-binaphthyl)2*NEt₃ calcium hydroxide 、 氢气 作用下， 以 甲醇 为溶剂， 25.0 ℃ 、7.09 MPa 条件下， 反应 12.0h， 生成 (R)-2-n-hexylcyclopentanone
  参考文献：
  名称：

  Synthesis and odor of optically active 2-n-hexyl- and 2-n-heptylcyclopentanone and the corresponding δ-lactones

  摘要：

  Enantiomeric 2-n-hexyl- and 2-n-heptylcyclopentanones (3) and (4) have been synthesized by asymmetric hydrogenation of 2-n-hexylidene and 2-n-heptylidenecyclopentanones (1) and (2) with Ru2Cl4[p-tolyl-binap](2)NEt3 complexes. The differences in odor qualities between enantiomeric pairs of the ketones 3 and 4 have been found to be small, and the same odor threshold values have been observed between the enantiomeric pairs, although the corresponding delta-undeca- and delta-dodecalactones (6) and (7), synthesized by Baeyer-Villiger oxidation of the chiral ketones 3 and 4, showed a fairly large difference in the threshold values between the enantiomeric pairs. (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(02)02312-2

文献信息

• Cascade Biotransformations via Enantioselective Reduction, Oxidation, and Hydrolysis: Preparation of (<i>R</i>)-δ-Lactones from 2-Alkylidenecyclopentanones
  作者：Ji Liu、Zhi Li

  DOI：10.1021/cs400101v

  日期：2013.5.3

  cascade biotransformation involving enantioselective reduction of a C═C double bond, Baeyer–Villiger oxidation, and lactone hydrolysis was developed as a green and sustainable tool for synthesizing enantiopure δ-lactones. One-pot cascade biotransformations were achieved with Acinetobacter sp. RS1 containing a novel enantioselective reductase and an enantioselective lactone hydrolase and Escherichia coli

  作为涉及绿色和可持续的合成对映纯δ-内酯的工具，首次涉及级联生物转化涉及C═C双键的对映选择性还原，Baeyer-Villiger氧化和内酯水解。不动杆菌属一锅级联生物转化。RS1含有新颖的对映选择性还原酶和对映体选择性内酯水解酶和大肠杆菌共表达的环己酮单加氧酶和葡糖脱氢酶，转换容易获得的2- alkylidenecyclopentanones 1 - 2成相应的有价值的香精香料（[R）-δ-内酯5 - 6在高ee中。一锅法合成优于报道的两步法制备。该概念对于开发其他包含C═C双键的底物的氧化还原级联反应很有用。
• Enoyl acyl carrier protein reductase (FabI) catalyzed asymmetric reduction of the CC double bond of α,β-unsaturated ketones: preparation of (R)-2-alkyl-cyclopentanones
  作者：Ji Liu、Jinchuan Wu、Zhi Li

  DOI：10.1039/c4cc04150j

  日期：——

  Enoyl-ACP reductase (FabI) was identified as a non-OYE 'ene'-reductase for asymmetric reduction of the C=C double bond of alpha, beta-unsaturated ketones. Reduction of several 2-alkylidenecyclopentanones with A-FabI and E-FabI gave (R)-2-alkylcyclopentanones in 95-90% and 70-81% ee, respectively. The product ee was improved to 99-98% in high yield by subsequent one-pot biooxidation.

  烯丙基ACP还原酶（FabI）被鉴定为非OYE'烯'还原酶，用于不对称还原α，β-不饱和酮的C = C双键。用A-FabI和E-FabI还原几种2-亚烷基环戊酮，分别得到95-90％和70-81％ee的（R）-2-烷基环戊酮。通过随后的一锅式生物氧化，产物ee以高产率提高至99-98％。
• Enantio- and Regioselective Baeyer−Villiger Oxidations of 2- and 3-Substituted Cyclopentanones Using Engineered Bakers' Yeast
  作者：Margaret M. Kayser、Gang Chen、Jon D. Stewart

  DOI：10.1021/jo980737v

  日期：1998.10.1
• Synthesis and odor of optically active 2-n-hexyl- and 2-n-heptylcyclopentanone and the corresponding δ-lactones
  作者：Takeshi Yamamoto、Miharu Ogura、Akira Amano、Kenichiro Adachi、Toshimitsu Hagiwara、Tsuneyoshi Kanisawa

  DOI：10.1016/s0040-4039(02)02312-2

  日期：2002.12

  Enantiomeric 2-n-hexyl- and 2-n-heptylcyclopentanones (3) and (4) have been synthesized by asymmetric hydrogenation of 2-n-hexylidene and 2-n-heptylidenecyclopentanones (1) and (2) with Ru2Cl4[p-tolyl-binap](2)NEt3 complexes. The differences in odor qualities between enantiomeric pairs of the ketones 3 and 4 have been found to be small, and the same odor threshold values have been observed between the enantiomeric pairs, although the corresponding delta-undeca- and delta-dodecalactones (6) and (7), synthesized by Baeyer-Villiger oxidation of the chiral ketones 3 and 4, showed a fairly large difference in the threshold values between the enantiomeric pairs. (C) 2002 Published by Elsevier Science Ltd.