(S)-2-乙基环戊酮 | 133907-27-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: (S)-2-乙基环戊酮
• 英文名称: (S)-2-ethylcyclopentanone
• 英文别名: Ethyl-(2)-cyclopentanon；(2S)-2-ethylcyclopentan-1-one
• CAS: 133907-27-4
• 化学式: C₇H₁₂O
• mdl: MFCD00019314
• 分子量: 112.172
• InChiKey: PPTKUTYPOKHBTL-LURJTMIESA-N

物化性质

• 沸点：
  163.5±8.0 °C(Predicted)
• 密度：
  0.913±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  (E)-2-benzylidenecyclopentan-1-ol 在 sodium periodate 、 rhodium(III) chloride hydrate 、 candida antarcticalipase B 、 C₁₂H₁₆ClO₂Ru 、 sodium carbonate 、 copper(l) chloride 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 甲苯 、 乙腈 为溶剂， 反应 48.42h， 生成 (S)-2-乙基环戊酮
  参考文献：
  名称：

  金属和酶催化从环烯丙基醇制得酮和内酯的对映选择性路线

  摘要：

  已经开发了合成对映体纯的α-取代的酮和相应的内酯的通用且有效的途径。钌和酶催化的动态动力学拆分（DKR）以及随后的Cu催化的α-烯丙基取代是该路线的关键步骤。以高收率和优异的对映体过量获得α-取代的酮。通过随后的Baeyer-Villiger氧化，该方法学被用于合成天然己内酯（R）-10-甲基-6-十一烷醇。

  DOI：

  10.1021/ol302358j

文献信息

• Asymmetric Transformation of Enones with<i>Synechococcus</i>sp. PCC 7942
  作者：Kei Shimoda、Naoji Kubota、Hiroki Hamada、Shin-ya Yamane、Toshifumi Hirata

  DOI：10.1246/bcsj.77.2269

  日期：2004.12

  transformation of enones was investigated with cultured cells of Synechococcus sp. PCC 7942 (a cyanobacterium). The cells reduced both the endocyclic C-C double bond of s-trans enones and the exocyclic C-C double bond of s-cis enones with high enantioselectivity to afford optically active α-substituted (S)-ketones under illumination. In addition, the reduction of the double bond of these enones was accompanied

  用聚球藻的培养细胞研究了烯酮的不对称转化。PCC 7942（一种蓝细菌）。细胞以高对映选择性减少了 s-trans enones 的内环 CC 双键和 s-cis enones 的外环 CC 双键，以在光照下提供光学活性的 α-取代 (S)-酮。此外，这些烯酮双键的还原伴随着饱和醇的形成。细胞优先将简单的脂肪酮而不是环状酮还原为相应的（S）-醇，具有出色的对映选择性。
• Synthetic ligands that modulate the activity of the RhlR quorum sensing receptor
  申请人：Wisconsin Alumni Research Foundation

  公开号：US11247976B2

  公开（公告）日：2022-02-15

  RhlR modulators including agonist and antagonists which are useful for modulating QS phenotypes in Gram-negative bacteria. Certain compounds of general formula A-W-HG having various carbocyclic ad heterocyclic head groups (HG) and various tail groups (A), where —W— is —CO—NH—, —SO2—NH—, —CO—NH—CH2—, or —SO2—NH—CH2— are RhlR agonists or antagonists. The compounds are useful in methods of modulating quorum sensing in Gram-negative bacteria, particularly in Pseudomonas. Compositions including certain RhlR modulators are useful for decreasing the virulence of Gram-negative bacteria. Pharmaceutical compositions comprising certain RhlR modulators are useful for treatment of infections of Gram-negative bacteria.

  RhlR 调节剂，包括激动剂和拮抗剂，可用于调节革兰氏阴性细菌的 QS 表型。通式 A-W-HG 的某些化合物具有各种碳环或杂环头基 (HG) 和各种尾基 (A)，其中 -W- 是 -CO-NH-、-SO2-NH-、-CO-NH-CH2- 或 -SO2-NH-CH2- 是 RhlR 激动剂或拮抗剂。这些化合物可用于调节革兰氏阴性细菌，特别是假单胞菌的法定量感应。包括某些 RhlR 调节剂的组合物有助于降低革兰氏阴性细菌的毒力。包含某些 RhlR 调节剂的药物组合物可用于治疗革兰氏阴性细菌感染。
• Asymmetric reduction of α,β-unsaturated carbonyl compounds with reductases from Nicotiana tabacum
  作者：Kei Shimoda、Naoji Kubota、Hiroki Hamada

  DOI：10.1016/j.tetasy.2004.07.011

  日期：2004.8

  Two reductases, p44 and p90, isolated from Nicotiana tabacum, catalyzed the asymmetric: reduction of alpha,beta-unsaturated carbonyl compounds. The p44 reductase reduced alpha-alkylated enones to (R)-ketones, while the reduction using the p90 reductase gave the (S)-ketones. The p90 reductase reduced beta-alkylated enones with excellent enantioselectivities to afford the (S)-ketones. On the other hand, the hydrogenation of the C-C double bond of 2-methylmaleimide with both enzymes gave (R)-2-methylsuccinimide. (C) 2004 Elsevier Ltd. All rights reserved.
• Synthetic Ligands that Modulate the Activity of the RhlR Quorum Sensing Receptor
  申请人：Wisconsin Alumni Research Foundation

  公开号：US20190144407A1

  公开（公告）日：2019-05-16

  RhlR modulators including agonist and antagonists which are useful for modulating QS phenotypes in Gram-negative bacteria. Certain compounds of general formula A-W-HG having various carbocyclic ad heterocyclic head groups (HG) and various tail groups (A), where —W— is —CO—NH—, —SO 2 —NH—, —CO—NH—CH 2 —, or —SO 2 —NH—CH 2 — are RhlR agonists or antagonists. The compounds are useful in methods of modulating quorum sensing in Gram-negative bacteria, particularly in Pseudomonas . Compositions including certain RhlR modulators are useful for decreasing the virulence of Gram-negative bacteria. Pharmaceutical compositions comprising certain RhlR modulators are useful for treatment of infections of Gram-negative bacteria.
• Enantioselective Route to Ketones and Lactones from Exocyclic Allylic Alcohols via Metal and Enzyme Catalysis
  作者：Madeleine C. Warner、Anuja Nagendiran、Krisztián Bogár、Jan-E. Bäckvall

  DOI：10.1021/ol302358j

  日期：2012.10.5

  A general and efficient route for the synthesis of enantiomerically pure α-substituted ketones and the corresponding lactones has been developed. Ruthenium- and enzyme-catalyzed dynamic kinetic resolution (DKR) with a subsequent Cu-catalyzed α-allylic substitution are the key steps of the route. The α-substituted ketones were obtained in high yields and with excellent enantiomeric excess. The methodology

  已经开发了合成对映体纯的α-取代的酮和相应的内酯的通用且有效的途径。钌和酶催化的动态动力学拆分（DKR）以及随后的Cu催化的α-烯丙基取代是该路线的关键步骤。以高收率和优异的对映体过量获得α-取代的酮。通过随后的Baeyer-Villiger氧化，该方法学被用于合成天然己内酯（R）-10-甲基-6-十一烷醇。