Ethyl 4,5-dimethyl-3-oxooctanoate | 910561-20-5

• 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: Ethyl 4,5-dimethyl-3-oxooctanoate
• 英文别名: ethyl 4,5-dimethyl-3-oxooctanoate
• CAS: 910561-20-5
• 化学式: C₁₂H₂₂O₃
• 分子量: 214.305
• InChiKey: AUJGBGNNDRUEAA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  15
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  乙酸铵 、 Ethyl 4,5-dimethyl-3-oxooctanoate 在 乙酸酐 作用下， 以 吡啶 、 甲醇 为溶剂， 以77%的产率得到C₁₅H₂₇NO₃
  参考文献：
  名称：

  The efficient synthesis of (3R,4R,5R)-3-amino-4,5-dimethyl-octanoic acid, a chiral β-amino acid with potent affinity for the α2δ protein

  摘要：

  A chiral beta-amino acid containing three contiguous chiral centers was synthesized efficiently in 11 steps, employing enantio-enriched beta-ketoester as a key intermediate, via stereoselective catalytic hydrogenation of the corresponding enamide. Stereoselective 1,4-addition of a methyl group and protonation were key to the preparation of the desired acid 12. Mild and efficient reaction conditions were applied to the enamine formation and protection to avoid epimerization at C-4 of compounds 13 and 14. The final compound was found to display potent affinity for the alpha(2)delta-protein that is a recognized drug target for the treatment of a variety of diseases. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.12.111
• 作为产物：
  描述：

  2,3-二甲基己酸 、 ethyl potassium malonate 在 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 为溶剂， 以57%的产率得到Ethyl 4,5-dimethyl-3-oxooctanoate
  参考文献：
  名称：

  The efficient synthesis of (3R,4R,5R)-3-amino-4,5-dimethyl-octanoic acid, a chiral β-amino acid with potent affinity for the α2δ protein

  摘要：

  A chiral beta-amino acid containing three contiguous chiral centers was synthesized efficiently in 11 steps, employing enantio-enriched beta-ketoester as a key intermediate, via stereoselective catalytic hydrogenation of the corresponding enamide. Stereoselective 1,4-addition of a methyl group and protonation were key to the preparation of the desired acid 12. Mild and efficient reaction conditions were applied to the enamine formation and protection to avoid epimerization at C-4 of compounds 13 and 14. The final compound was found to display potent affinity for the alpha(2)delta-protein that is a recognized drug target for the treatment of a variety of diseases. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.12.111

文献信息

• [EN] PREPARATION OF BETA-AMINO ACID PRECURSORS VIA INDIUM (III) MEDIATED MARKOVNIKOV ADDITION AND KNOEVENAGEL CONDENSATION<br/>[FR] PREPARATION DE PRECURSEURS DE BETA-AMINOACIDE PAR ADDITION DE MARKOVNIKOV ET CONDENSATION DE KNOEVENAGEL A MEDIATION ASSUREE PAR DE L'INDIUM (III)
  申请人：WARNER LAMBERT CO

  公开号：WO2006100606A2

  公开（公告）日：2006-09-28

  (EN) Disclosed are materials and methods for preparing precursors of optically active &bgr;-amino acids, which bind to the alpha-2-delta (&agr;2&dgr;) subunit of a calcium channel and are useful for treating pain, fibromyalgia, and a variety of psychiatric and sleep disorders. The method includes reacting a malonate derivative with a terminal alkyne in the presence of an In(III) catalyst.(FR) L'invention concerne des matériaux et des procédés pour la préparation de précurseurs de ß-aminoacides optiquement actifs, qui se lient à la sous-unité alpha-2-delta (a2d) d'un canal calcique et qui sont utiles pour le traitement de la douleur, de la fibromyalgie, et de divers troubles psychiatriques ou du sommeil. Le procédé de l'invention consiste à faire réagir un dérivé de malonate avec un alcyne terminal en présence d'un catalyseur In(III).
• The efficient synthesis of (3R,4R,5R)-3-amino-4,5-dimethyl-octanoic acid, a chiral β-amino acid with potent affinity for the α2δ protein
  作者：Ji Zhang、Peter G. Blazecka、Derek A. Pflum、Joseph Bozelak、Derek Vrieze、Norman L. Colbry、Garrett Hoge、David C. Boyles、Brian Samas、Timothy T. Curran、Augustine T. Osuma、Paul Johnson、Suzanne Kesten、Jacob B. Schwarz、Annise Goodman、Mark Plummer、Anne Akin、Yun Huang、Michael Lovdahl、Andrew J. Thorpe

  DOI：10.1016/j.tetlet.2008.12.111

  日期：2009.3

  A chiral beta-amino acid containing three contiguous chiral centers was synthesized efficiently in 11 steps, employing enantio-enriched beta-ketoester as a key intermediate, via stereoselective catalytic hydrogenation of the corresponding enamide. Stereoselective 1,4-addition of a methyl group and protonation were key to the preparation of the desired acid 12. Mild and efficient reaction conditions were applied to the enamine formation and protection to avoid epimerization at C-4 of compounds 13 and 14. The final compound was found to display potent affinity for the alpha(2)delta-protein that is a recognized drug target for the treatment of a variety of diseases. (C) 2009 Elsevier Ltd. All rights reserved.