methyl 5-cyclopropyl-3,5-dioxohexanoate

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl 5-cyclopropyl-3,5-dioxohexanoate
• 英文别名: Methyl 5-cyclopropyl-3,5-dioxopentanoate
• 化学式: C₉H₁₂O₄
• 分子量: 184.192
• InChiKey: HEFAAUVIQPKPGQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  1.0
• 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：

  methyl 5-cyclopropyl-3,5-dioxohexanoate 、 碘甲烷 在 caesium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 12.5h， 以22%的产率得到methyl 5-cyclopropyl-3,5-dioxo-2,2,4,4-tetramethylpentanoate
  参考文献：
  名称：

  Synthesis and characterization of permethylated 1,3,5-tri- and 1,3,5,7-tetracarbonyl compounds

  摘要：

  Permethylated 1,3,5-tri- and 1,3,5,7-tetracarbonyl compounds were prepared and structurally characterized. 2,2,4,4-Tetramethyl-3,5-dioxoesters were prepared by condensation of 1,3-bis(trimethylsilyloxy)-1,3-butadienes with acid chlorides and subsequent reaction with methyl iodide. 2,2,4,4,6,6-Hexa-substituted 3,5-dioxopimelates were prepared by condensation of 1,3-bis(trimethylsilyloxy)-1,3-butadienes with methyl 3-chloro-3-oxopropanoate and subsequent methylation. The use of caesium carbonate as the base for the methylation proved to be important to achieve good yields. The conformation of the products was studied by experimental and theoretical methods (DFT calculations). (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.08.065
• 作为产物：
  描述：

  1,3-bis(trimethylsiloxy)-1-methoxybuta-1,3-diene 、 环丙基甲酰氯 以 二氯甲烷 为溶剂， 以91%的产率得到methyl 5-cyclopropyl-3,5-dioxohexanoate
  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

• Synthesis and characterization of bis-cyclopropanated 1,3,5-tricarbonyl compounds. A combined synthetic, spectroscopic and theoretical study
  作者：Thomas Rahn、Franziska Bendrath、Martin Hein、Wolfgang Baumann、Haijun Jiao、Armin Börner、Alexander Villinger、Peter Langer

  DOI：10.1039/c1ob05455d

  日期：——

  Bis-cyclopropanated 1,3,5-tricarbonyl compounds were prepared by a sequence of Claisen condensations and cyclopropanations. The optimization of the conditions proved to be very important to suppress retro-Claisen reactions. The conformation of these molecules was studied by experimental and computational methods. The syn/syn;syn/syn conformation is present for all derivatives. It is exclusively present in the case of the derivative containing a phenyl group located at the terminal carbon atom. In most cases, equilibria with other conformers are found.

  双环丙烯化的1,3,5-三羰基化合物是通过一系列克莱森缩合反应和环丙烯化反应制备的。优化反应条件被证明对抑制逆克莱森反应非常重要。这些分子的构象通过实验和计算方法进行了研究。所有衍生物均呈现出syn/syn；syn/syn构象。在含有位于末端碳原子的苯基的衍生物中，该构象是独占性的。在大多数情况下，还发现与其他构象体的平衡。
• Heteroarylcarboxamide compounds active against protein tyrosine kinase related disorders
  申请人：Sugen, Inc.

  公开号：US20040102489A1

  公开（公告）日：2004-05-27

  The present invention relates to novel heteroaryl-carboxamides which modulate the activity of protein tyrosine kinases and therefore are expected to be useful in the treatment of abnormal protein tyrosine kinase activity driven disorders including cancer.

  本发明涉及一种新型杂环基-羧酰胺，其可以调节蛋白酪氨酸激酶的活性，因此被期望在治疗异常的蛋白酪氨酸激酶活性驱动的疾病，包括癌症中有用。
• EP1012150A4
  申请人：——

  公开号：EP1012150A4

  公开（公告）日：2002-05-29
• HETEROARYLCARBOXAMIDE COMPOUNDS ACTIVE AGAINST PROTEIN TYROSINE KINASE RELATED DISORDERS
  申请人：Sugen, Inc.

  公开号：EP1012150A1

  公开（公告）日：2000-06-28
• US6316479B1
  申请人：——

  公开号：US6316479B1

  公开（公告）日：2001-11-13