(S)-2-heptylcyclopentanone | 553612-01-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-2-heptylcyclopentanone
• 英文别名: (2S)-2-heptylcyclopentan-1-one
• CAS: 553612-01-4
• 化学式: C₁₂H₂₂O
• 分子量: 182.306
• InChiKey: PJXHBTZLHITWFX-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 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)-2-heptylcyclopentanone 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 (S)-δ-dodecalactone
  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：

  (E)-2-n-heptylidenecyclopentanone 在 Ru₂Cl₄((R)-(+)-2,2'-bis(di-p-tolylphosphino)-1,1'-binaphthyl)2*NEt₃ 氢气 作用下， 以 甲醇 为溶剂， 25.0 ℃ 、7.09 MPa 条件下， 反应 12.0h， 以88%的产率得到(S)-2-heptylcyclopentanone
  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％。
• Novozyme 435 Asymmetric Hydrolysis of Enol Ester with Series Acid Moiety
  作者：Quan Li、Weimin Jia、Zhijian Wang、Xiaodan Guo

  DOI：10.14233/ajchem.2014.16200

  日期：——

  (R)-2-pentylcyclopentanone can be synthesized by the asymmetric hydrolysis of enol esters, catalyzed by immobilized candida antarctica (novozyme 435) lipase. Different acid moieties influence the stereoselectivity of lipase. Enol esters can be prepared from anhydrides and 2-pentylcyclopentanone. When introducing optical (S)-(+)-2-methyl-butyric acid, the hydrolysis of optical enol ester showed great enhancement of the specific rotation compared to the racemic enol ester, the specific rotation of product raise from [a]25D-10° (c 0.1, CH3OH) to [a]25D-72° (c 0.1, CH3OH). However, when bringing chiral acid moity, the specific rotation still can not catch up with the value compared to the isobutyric moiety. The specific rotation of (R)-2-pentylcyclopentanone is [a]25D-102.20° (c 0.1, CH3OH), the optimum temperature and pH were 30 °C and 6.5, respectively. Then 81.06 % ee of (R)-d-decalactone was prepared by the Baeyer-Villiger oxidation of (R)-2-pentylcyclopentanone.

  (R)-2-戊基环戊酮可以通过固定化南极假丝酵母 (novozyme 435) 脂肪酶催化烯醇酯的不对称水解来合成。不同的酸部分影响脂肪酶的立体选择性。烯醇酯可由酸酐和2-戊基环戊酮制备。当引入光学(S)-(+)-2-甲基-丁酸时，光学烯醇酯的水解比外消旋烯醇酯表现出比旋光度大大增强，产物的比旋光度从[a]25D-升高10°（c 0.1，CH3OH）至[a]25D-72°（c 0.1，CH3OH）。然而，当引入手性酸部分时，与异丁酸部分相比，比旋光度仍然无法赶上该值。 (R)-2-戊基环戊酮的比旋光度为[a]25D-102.20°(c 0.1,CH3OH)，最适温度和pH分别为30℃和6.5。然后通过(R)-2-戊基环戊酮的Baeyer-Villiger氧化制备81.06％ee的(R)-d-癸内酯。
• 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.