[(1R,5S)-5-methyl-4-oxocyclohex-2-en-1-yl] (2R)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoate | 1123211-32-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [(1R,5S)-5-methyl-4-oxocyclohex-2-en-1-yl] (2R)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoate
• CAS: 1123211-32-4
• 化学式: C₁₇H₁₇F₃O₄
• 分子量: 342.315
• InChiKey: BEMRSWBOPWZEBF-DETPVDSQSA-N

物化性质

• 沸点：
  439.0±45.0 °C(predicted)
• 密度：
  1.27±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (4R,6S)-4-hydroxy-6-methylcyclohex-2-enone 、 (R)-(+)-α-甲氧基-α-(三氟甲基)苯乙酸 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 168.0h， 以0.6 mg的产率得到[(1R,5S)-5-methyl-4-oxocyclohex-2-en-1-yl] (2R)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoate
  参考文献：
  名称：

  Polyoxygenated Methyl Cyclohexanoids from a Terrestrial Ampelomyces Fungus

  摘要：

  Seven structurally related new polyoxygenated methyl cyclohexanoids, ampelomins A-G (1-7), were isolated from the mycelial solid culture of a soil-derived Ampelornyces fungus. Their structures were determined by spectroscopic and chemical means. Ampelomins A (1), C (3), E (5), and G (7) exhibited weak activity against a-glucosidase with IC50 values of 1.74-5.93 mM, and ampelomin A (1) showed moderate antibacterial activity with MIC90 values ranging from 202.4 to 1015.9 mu M. A plausible polyketide biogenetic pathway is postulated for these compounds.

  DOI：

  10.1021/np800667e

文献信息

• Synthesis of 4-Hydroxy-5-methyl- and 4-Hydroxy-6-methylcyclohexenones by PdII-Catalyzed Oxidation and Lipase-Catalyzed Hydrolysis
  作者：Anne C. Meister、Martin Nieger、Stefan Bräse

  DOI：10.1002/ejoc.201200704

  日期：2012.9

  A short route for the syntheses of methyl-substituted hydroxycyclohexenones, which are building blocks for various natural products, is presented. Both oxygen atoms were introduced as acetates by a palladium(II)-catalyzed 1,4-addition to a 1,3-diene. The distinction between the two acetoxy groups was achieved by regioselective monohydrolysis with lipase from Candida rugosa, which gave 1-acetoxy-4-

  介绍了合成甲基取代的羟基环己烯酮的一条捷径，它们是各种天然产物的基石。通过钯 (II) 催化的 1,4-加成到 1,3-二烯，将两个氧原子作为乙酸盐引入。两个乙酰氧基之间的区别是通过用来自 Candida rugosa 的脂肪酶进行区域选择性单水解来实现的，得到 1-乙酰氧基-4-羟基-5-甲基环己烯及其 6-甲基区域异构体作为可分离的混合物。目标化合物 4-羟基-5-甲基环己-2-烯酮和 4-羟基-6-甲基环己-2-烯酮可以作为非对映体混合物以良好的总产率和适度的对映体过量（31-67%）获得。
• Polyoxygenated Methyl Cyclohexanoids from a Terrestrial <i>Ampelomyces</i> Fungus
  作者：Huiye Zhang、Jinghua Xue、Ping Wu、Liangxiong Xu、Haihui Xie、Xiaoyi Wei

  DOI：10.1021/np800667e

  日期：2009.2.27

  Seven structurally related new polyoxygenated methyl cyclohexanoids, ampelomins A-G (1-7), were isolated from the mycelial solid culture of a soil-derived Ampelornyces fungus. Their structures were determined by spectroscopic and chemical means. Ampelomins A (1), C (3), E (5), and G (7) exhibited weak activity against a-glucosidase with IC50 values of 1.74-5.93 mM, and ampelomin A (1) showed moderate antibacterial activity with MIC90 values ranging from 202.4 to 1015.9 mu M. A plausible polyketide biogenetic pathway is postulated for these compounds.