(R)-N-methoxy-N,3-dimethyl-5-oxopentanamide | 158041-63-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-N-methoxy-N,3-dimethyl-5-oxopentanamide
• 英文别名: (-)-(R)-3-(formylmethyl)-N-methoxy-N-methylbutanamide；(3R)-N-methoxy-N,3-dimethyl-5-oxopentanamide
• CAS: 158041-63-5
• 化学式: C₈H₁₅NO₃
• 分子量: 173.212
• InChiKey: VJWKZAJKQAIBSE-SSDOTTSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-N-methoxy-N,3-dimethyl-5-oxopentanamide 在 sodium amalgam 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 反应 2.0h， 生成 (3R,5E,7E)-N-methoxy-N,3-dimethylnona-5,7-dienamide
  参考文献：
  名称：

  Enantioselective Total Synthesis of (+)-6-epi-Mevinolin and Its Analogs. Efficient Construction of the Hexahydronaphthalene Moiety by High Pressure-Promoted Intramolecular Diels−Alder Reaction of (R,2Z,8E,10E)-1-[(tert-Butyldimethylsilyl)oxy]-6-methyl-2,8,10-dodecatrien-4-one

  摘要：

  3-Hydroxy-3-methylglutaryl coenzyme A (HMG-CoA) reductase inhibitors, (+)-6-epi-mevinolin (2a) and (+)-6-epi-4a,5-dihydromevinolin (2b), were prepared by combining two nonracemic units, phosphonate 3 and decalin 4, which were prepared from enantiopure 3-substituted pentanedioic acid monoesters 5a and 5b, respectively. Each acid was synthesized from cyclic anhydrides 7a and 7b by diastereoselective ring opening by means of (S)-benzyl mandelate as a common chiral auxiliary. The construction of decalin moiety 4 was accomplished by asymmetric intramolecular Diels-Alder (IMDA) reaction of nonracemic trienone 6 bearing a methyl group as a chiral controller. The IMDA diastereoselectivity of trienone 6 is discussed in terms of the configuration of(E)- and (Z)-dienophiles which are activated by an endogenous carbonyl group. The IMDA reaction of(R)-(Z)-6 under high pressure is highly selective and gives cis-decalins exclusively with preferential formation of 4 over 16. The inhibitory activity of (+)-6-epi-mevinolin (2a) and several analogs against HMG-CoA reductase was compared with mevinolin (1b). (+)-6-epi-Mevinolin (2a) was shown to be half as potent as mevinolin (1b) while (+)-6-epi-4a,5-dihydromevinolin (2b) was as potent as mevinolin.

  DOI：

  10.1021/jo970444m
• 作为产物：
  描述：

  (4R)-4-methyltetrahydro-2H-pyran-2-one 在 重铬酸吡啶 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 25.0 ℃ 、900.0 MPa 条件下， 反应 11.5h， 生成 (R)-N-methoxy-N,3-dimethyl-5-oxopentanamide
  参考文献：
  名称：

  Enantioselective Total Synthesis of (+)-6-epi-Mevinolin and Its Analogs. Efficient Construction of the Hexahydronaphthalene Moiety by High Pressure-Promoted Intramolecular Diels−Alder Reaction of (R,2Z,8E,10E)-1-[(tert-Butyldimethylsilyl)oxy]-6-methyl-2,8,10-dodecatrien-4-one

  摘要：

  3-Hydroxy-3-methylglutaryl coenzyme A (HMG-CoA) reductase inhibitors, (+)-6-epi-mevinolin (2a) and (+)-6-epi-4a,5-dihydromevinolin (2b), were prepared by combining two nonracemic units, phosphonate 3 and decalin 4, which were prepared from enantiopure 3-substituted pentanedioic acid monoesters 5a and 5b, respectively. Each acid was synthesized from cyclic anhydrides 7a and 7b by diastereoselective ring opening by means of (S)-benzyl mandelate as a common chiral auxiliary. The construction of decalin moiety 4 was accomplished by asymmetric intramolecular Diels-Alder (IMDA) reaction of nonracemic trienone 6 bearing a methyl group as a chiral controller. The IMDA diastereoselectivity of trienone 6 is discussed in terms of the configuration of(E)- and (Z)-dienophiles which are activated by an endogenous carbonyl group. The IMDA reaction of(R)-(Z)-6 under high pressure is highly selective and gives cis-decalins exclusively with preferential formation of 4 over 16. The inhibitory activity of (+)-6-epi-mevinolin (2a) and several analogs against HMG-CoA reductase was compared with mevinolin (1b). (+)-6-epi-Mevinolin (2a) was shown to be half as potent as mevinolin (1b) while (+)-6-epi-4a,5-dihydromevinolin (2b) was as potent as mevinolin.

  DOI：

  10.1021/jo970444m

文献信息

• Concise Enantioselective Total Synthesis of Neopeltolide Macrolactone Highlighted by Ether Transfer
  作者：Rendy Kartika、Thomas R. Gruffi、Richard E. Taylor

  DOI：10.1021/ol802254z

  日期：2008.11.6

  A concise total synthesis of neopeltolide macrolactone has been accomplished in 14 steps in the longest linear sequence, 15 steps overall from commercially available materials. The present synthesis was highlighted by successful exploitation of ether transfer methodology and a radical cyclization reaction to directly establish the requisite stereochemistry of the tetrahydropyran core.

  以最长的线性顺序仅用14个步骤即可完成新pelolide大内酯的简明总合成，从市售材料中总共可完成15个步骤。通过成功地利用醚转移方法和自由基环化反应来直接建立四氢吡喃核心的必要立体化学，突出了本发明的合成方法。
• Brown, M. Kevin; Hoveyda, Amir H., Journal of the American Chemical Society, 2008, vol. 130, p. 12904 - 12906
  作者：Brown, M. Kevin、Hoveyda, Amir H.

  DOI：——

  日期：——