3-Isopropenyl-6-oxo-heptansaeure | 4436-82-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: 3-Isopropenyl-6-oxo-heptansaeure
• 英文别名: (L)-4-methyl-3-(3-oxo-butyl)-pent-4-enoic acid；(L)-4-Methyl-3-(3-oxo-butyl)-pent-4-ensaeure；(-)(R)-6-Oxo-3-isopropenyl-heptansaeure-(1)；(3R)-3-isopropenyl-6-oxoheptanoic acid；(3R)-6-oxo-3-prop-1-en-2-ylheptanoic acid
• CAS: 4436-82-2
• 化学式: C₁₀H₁₆O₃
• 分子量: 184.235
• InChiKey: NJOIWWRMLFSDTM-SECBINFHSA-N

物化性质

• LogP：
  1.40

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2918300090

反应信息

• 作为反应物：
  描述：

  3-Isopropenyl-6-oxo-heptansaeure 在 4-二甲氨基吡啶 、 N,N-二异丙基乙胺 、 对甲苯磺酰氯 、 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以76%的产率得到(1S,2R,5R)-5-methyl-2-(prop-1-en-2-yl)-6-oxabicyclo[3.2.0]heptan-7-one
  参考文献：
  名称：

  A Diastereoselective, Nucleophile-Promoted Aldol-Lactonization of Ketoacids Leading to Bicyclic-β-Lactones

  摘要：

  An improved, tandem acid activation/aldol-lactonization process is described. This more practical protocol shortens reaction times for the construction of bicyclic beta-lactones from ketoacids and implements the use of commercially available reagents p-toluenesulfonyl chloride (p-TsC1) as activator and 4-dimethylaminopyridine (4-DMAP) as nucleophllic promoter (Lewis base). Substrates with beta-substituents, with respect to the carboxylic acid, consistently showed excellent levels of diastereoselectivity during the bis-cyclization event.

  DOI：

  10.1021/jo202252y
• 作为产物：
  描述：

  (4S)-1-methyl-4-(prop-1-en-2-yl)-7,8,9-trioxabicyclo[4.2.1]nonane 在 盐酸 作用下， 以 异丙醇 为溶剂， 生成 3-Isopropenyl-6-oxo-heptansaeure
  参考文献：
  名称：

  Ozonolytic Transformation of (S)-(–)-Limonene in HCl–Isopropanol

  摘要：

  (S)-(–)-柠檬烯 (ee 50%) 在环己烷:异丙醇中于 2–4°C 进行部分臭氧分解，形成 1,2,4-三氧戊环，为 3:2 比例的非对映异构体混合物。 HCl 的 i-PrOH 溶液在过氧化物分解过程中充当裂解剂，在非对映体 1,2,4-取代环己烷形成过程中充当环化剂。

  DOI：

  10.1007/s10600-015-1206-y

文献信息

• Probe compound for detecting and isolating enzymes and means and methods using the same
  申请人：Helmholtz-Zentrum für Infektionsforschung GmbH

  公开号：EP2230312A1

  公开（公告）日：2010-09-22

  The present invention relates to a probe compound that can comprise any substrate or metabolite of an enzymatic reaction in addition to an indicator component, such as, for example, a fluorescence dye, or the like. Moreover, the present invention relates to means for detecting enzymes in form of an array, which comprises any number of probe compounds of the invention which each comprise a different metabolite of interconnected metabolites representing the central pathways in all forms of life. Moreover, the present invention relates to a method for detecting enzymes involving the application of cell extracts or the like to the array of the invention which leads to reproducible enzymatic reactions with the substrates. These specific enzymatic reactions trigger the indicator (e.g. a fluorescence signal) and bind the enzymes to the respective cognate substrates. Moreover, the invention relates to means for isolating enzymes in form of nanoparticles coated with the probe compound of the invention. The immobilisation of the cognate substrates or metabolites on the surface of nanoparticles by means of the probe compounds allows capturing and isolating the respective enzyme, e.g. for subsequent sequencing.

  本发明涉及一种探针化合物，它可以包括酶反应的任何底物或代谢物，此外还包括指示成分，例如荧光染料或类似物。此外，本发明还涉及以阵列形式检测酶的方法，该阵列由任意数量的本发明探针化合物组成，每种探针化合物由代表所有生命形式中中心途径的相互关联的代谢物中的不同代谢物组成。此外，本发明还涉及一种检测酶的方法，该方法涉及将细胞提取物或类似物应用于本发明的阵列，从而导致与底物发生可重复的酶反应。这些特定的酶反应会触发指示剂（如荧光信号），并将酶与各自的同源底物结合。此外，本发明还涉及以涂覆有本发明探针化合物的纳米颗粒形式分离酶的方法。通过探针化合物将同源底物或代谢物固定在纳米颗粒表面，可以捕获和分离相应的酶，例如用于后续测序。
• Schmidt, Chemische Berichte, 1949, vol. 82, p. 11,13, 15
  作者：Schmidt

  DOI：——

  日期：——
• Total Synthesis of (+)-Omphadiol
  作者：Gang Liu、Daniel Romo

  DOI：10.1002/anie.201102289

  日期：2011.8.8
• Ozonolytic Transformation of (S)-(–)-Limonene in HCl–Isopropanol
  作者：G. Yu. Ishmuratov、Yu. V. Legostaeva、L. R. Garifullina、R. R. Muslukhov、L. P. Botsman、G. G. Kozlova

  DOI：10.1007/s10600-015-1206-y

  日期：2015.1

  Partial ozonolysis of (S)-(–)-limonene (ee 50%) in cyclohexane:isopropanol at 2–4°C formed the 1,2,4-trioxolane as a mixture of diastereomers in a 3:2 ratio. A solution of HCl in i-PrOH acted as a cleaving agent during decomposition of the peroxides and a cyclizing agent during formation of the diastereomeric 1,2,4-substituted cyclohexanes.

  (S)-(–)-柠檬烯 (ee 50%) 在环己烷:异丙醇中于 2–4°C 进行部分臭氧分解，形成 1,2,4-三氧戊环，为 3:2 比例的非对映异构体混合物。 HCl 的 i-PrOH 溶液在过氧化物分解过程中充当裂解剂，在非对映体 1,2,4-取代环己烷形成过程中充当环化剂。
• A Diastereoselective, Nucleophile-Promoted Aldol-Lactonization of Ketoacids Leading to Bicyclic-β-Lactones
  作者：Gang Liu、Morgan E. Shirley、Daniel Romo

  DOI：10.1021/jo202252y

  日期：2012.3.2

  An improved, tandem acid activation/aldol-lactonization process is described. This more practical protocol shortens reaction times for the construction of bicyclic beta-lactones from ketoacids and implements the use of commercially available reagents p-toluenesulfonyl chloride (p-TsC1) as activator and 4-dimethylaminopyridine (4-DMAP) as nucleophllic promoter (Lewis base). Substrates with beta-substituents, with respect to the carboxylic acid, consistently showed excellent levels of diastereoselectivity during the bis-cyclization event.