3,5-二羰基-辛酸甲酯 | 36568-09-9

• 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
• 中文名称: 3,5-二羰基-辛酸甲酯
• 英文名称: Methyl 3,5-dioxooctanoate
• 英文别名: Methyl-3,5-dioxooctanoat
• CAS: 36568-09-9
• 化学式: C₉H₁₄O₄
• 分子量: 186.208
• InChiKey: WIOUGEQKWPFNOB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  13
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  60.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,5-二羰基-辛酸甲酯 在 Ru₂Cl₄-(S)-(2,2'-bis(diphenylphosphino)-1,1'-binaphthyl)2*NEt₃ 正丁基锂 、 氢气 、 对甲苯磺酸 作用下， 反应 48.0h， 生成 (Z)-(S)-5-Hydroxy-oct-2-enoic acid ((R)-1-phenyl-ethyl)-amide
  参考文献：
  名称：

  Asymmetric hydrogenation of 3,5-Dioxoesters catalyzed by Ru-binap complex: A short step asymmetric synthesis of 6-substituted 5,6-dihydro-2-pyrones

  摘要：

  Asymmetric hydrogenation of 3,5-dioxoesters 1a-c using Ru2Cl4((R) or (S)-binap)2(NEt3) as the catalyst gave dominantly anti 3,5-dihydroxyesters 2, which were then converted into unsaturated lactones 5a-b (ca. 80% e.e.). The pathway of the hydrogenation reaction was also investigated by asymmetric hydrogenation of (R)- or (S)-5-hydroxy-3-oxoesters 8a-c. It was revealed that the Ru-binap catalyzed hydrogenation of 1a-b proceed dominantly via the beta-diketone mode. A convenient asymmetric synthesis of hydroxylactone 3c and unsaturated lactone 5c was presented.

  DOI：

  10.1016/s0040-4020(01)86300-6
• 作为产物：
  描述：

  1,3-bis(trimethylsiloxy)-1-methoxybuta-1,3-diene 、 丁酰氯 以 二氯甲烷 为溶剂， 以69%的产率得到3,5-二羰基-辛酸甲酯
  参考文献：
  名称：

  1,3-双（甲硅烷基烯醇醚）与酰氯的缩合反应合成1,3,5-三羰基衍生物

  摘要：

  在温和的条件下，通过1,3-双（甲硅烷基烯醇醚）与酰氯的反应，可以制得各种1,3,5-三羰基衍生物。这包括芳族和脂族酰氯与双（酰氯）的反应。收率根据所用酰氯的类型而变化。

  DOI：

  10.1021/jo062153w

文献信息

• The Acylation of β-Keto Ester Dianions
  作者：Stuart Nicholas Huckin、Larry Weiler

  DOI：10.1139/v74-205

  日期：1974.4.15

  A method for the successful acylation of the dianion of simple β-keto esters to yield β,δ-diketo esters has been developed. The dianion of methyl acetoacetate also reacts with the monoanion of meth...

  已经开发了一种成功酰化简单 β-酮酯的二价阴离子以产生 β,δ-二酮酯的方法。乙酰乙酸甲酯的双阴离子也与甲基的单阴离子反应...
• PYRIDAZINE AMIDE COMPOUNDS AND THEIR USE AS SYK INHIBITORS
  申请人：F. Hoffmann-La Roche AG

  公开号：EP2802567B1

  公开（公告）日：2017-03-01
• [EN] PYRIDAZINE AMIDE COMPOUNDS AND THEIR USE AS SYK INHIBITORS<br/>[FR] COMPOSÉS DE PYRIDAZINAMIDE ET LEUR UTILISATION EN TANT QU'INHIBITEURS DE SYK
  申请人：HOFFMANN LA ROCHE

  公开号：WO2013104573A1

  公开（公告）日：2013-07-18

  The present invention relates to the use of novel triazolopyridine derivatives of formula (I): wherein all variable substituents are defined as described herein, which are SYK inhibitors and are useful for the treatment of auto-immune and inflammatory diseases.
• Asymmetric hydrogenation of 3,5-Dioxoesters catalyzed by Ru-binap complex: A short step asymmetric synthesis of 6-substituted 5,6-dihydro-2-pyrones
  作者：Liming Shao、Hiroyuki Kawano、Masahiko Saburi、Yasuzo Uchida

  DOI：10.1016/s0040-4020(01)86300-6

  日期：1993.3

  Asymmetric hydrogenation of 3,5-dioxoesters 1a-c using Ru2Cl4((R) or (S)-binap)2(NEt3) as the catalyst gave dominantly anti 3,5-dihydroxyesters 2, which were then converted into unsaturated lactones 5a-b (ca. 80% e.e.). The pathway of the hydrogenation reaction was also investigated by asymmetric hydrogenation of (R)- or (S)-5-hydroxy-3-oxoesters 8a-c. It was revealed that the Ru-binap catalyzed hydrogenation of 1a-b proceed dominantly via the beta-diketone mode. A convenient asymmetric synthesis of hydroxylactone 3c and unsaturated lactone 5c was presented.
• Synthesis of 1,3,5-Tricarbonyl Derivatives by Condensation of 1,3-Bis(silyl enol ethers) with Acid Chlorides
  作者：Thomas Rahn、Van T. H. Nguyen、T. H. Tam Dang、Zafar Ahmed、Karen Methling、Michael Lalk、Christine Fischer、Anke Spannenberg、Peter Langer

  DOI：10.1021/jo062153w

  日期：2007.3.1

  A variety of 1,3,5-tricarbonyl derivatives were prepared by reaction of 1,3-bis(silyl enol ethers) with acid chlorides under mild conditions. This includes reactions of both aromatic and aliphatic acid chlorides and bis(acid chlorides). The yields vary depending on the type of acid chloride employed.

  在温和的条件下，通过1,3-双（甲硅烷基烯醇醚）与酰氯的反应，可以制得各种1,3,5-三羰基衍生物。这包括芳族和脂族酰氯与双（酰氯）的反应。收率根据所用酰氯的类型而变化。