2-环丙基-3-氧代丙酸甲酯 | 72306-36-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-环丙基-3-氧代丙酸甲酯
• 英文名称: methyl 2-cyclopropyl-3-aldehydeacetate
• 英文别名: methyl 2-cyclopropyl-3-oxopropanoate；Methyl-α-formyl-cyclopropyl-acetat
• CAS: 72306-36-6
• 化学式: C₇H₁₀O₃
• 分子量: 142.155
• InChiKey: JGNGDWDHTUVQIJ-UHFFFAOYSA-N

物化性质

• 沸点：
  65-70 °C(Press: 1.6 Torr)
• 密度：
  1.158±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 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：

  2-环丙基-3-氧代丙酸甲酯 在 N,N-二异丙基乙胺 、 三氯氧磷 作用下， 以 四氢呋喃 、 甲醇 、 异丙醇 为溶剂， 生成 N-(3-((2-chloro-5-cyclopropylpyrimidin-4-yl)amino)propyl)cyclobutanecarboxamide
  参考文献：
  名称：

  Synthesis and structure–activity relationships of a novel series of pyrimidines as potent inhibitors of TBK1/IKKε kinases

  摘要：

  The design, synthesis and structure-activity relationships of a novel series of 2,4-diamino-5-cyclopropyl pyrimidines is described. Starting from BX795, originally reported to be a potent inhibitor of PDK1, we have developed compounds with improved selectivity and drug-like properties. These compounds have been evaluated in a range of cellular and in vivo assays, enabling us to probe the putative role of the TBK1/IKK epsilon pathway in inflammatory diseases. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.09.063
• 作为产物：
  描述：

  甲基环丙基醋酸 、 甲酸乙酯 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以90%的产率得到2-环丙基-3-氧代丙酸甲酯
  参考文献：
  名称：

  发现新型的4-（2-嘧啶基氨基）苯甲酰胺衍生物作为高效和可口服的刺猬信号通路抑制剂

  摘要：

  基于以前报道的4-（2-嘧啶基氨基）苯甲酰胺的支架，通过结构修饰设计了一系列新颖的刺猬信号途径抑制剂。描述了该系列的SAR，许多衍生物显示出有效的抑制活性。在这些化合物中，化合物12af和12bf被确定具有高效力和最佳PK分布。尽管化合物12af和12bf在LS-174T裸鼠模型中均未显示出强大的抗肿瘤功效，但由于它们对Hh信号通路的强大效力和出色的PK特性，它们有望成为Hh信号抑制剂的候选者，值得在其他Hh信号手术中进一步评估肿瘤模型。

  DOI：

  10.1016/j.ejmech.2016.01.018

文献信息

• 作为Hedgehog信号传导的嘧啶胺类和吡啶胺 类抑制剂
  申请人：江苏先声药业有限公司

  公开号：CN103864770B

  公开（公告）日：2019-06-11

  本发明涉及作为Hedgehog信号传导的嘧啶胺类和吡啶胺类抑制剂，其为具式（I）结构的化合物或其药学上可接受的盐，本发明还涉及这些化合物可以作为hedgehog信号传导抑制剂的医药用途。
• The discovery of novel N-(2-pyrimidinylamino) benzamide derivatives as potent hedgehog signaling pathway inhibitors
  作者：Minhang Xin、Jun Wen、Feng Tang、Chongxing Tu、Han Shen、Xinge Zhao

  DOI：10.1016/j.bmcl.2013.10.022

  日期：2013.12

  Hedgehog signaling pathway inhibitors are emerging as new therapeutic intervention against cancer. A novel series of N-(2-pyrimidinylamino) benzamide derivatives as hedgehog signaling pathway inhibitors were designed and synthesized. Most compounds presented significant inhibitory effect on hedgehog signaling pathway, among which 21 compounds exhibited more potent than vismodegib. Furthermore, compound 6a showed moderate pharmacokinetic properties in vivo, representing a promising lead compound for further exploration. (C) 2013 Elsevier Ltd. All rights reserved.
• Basnak,I.; Farkas,J., Collection of Czechoslovak Chemical Communications, 1979, vol. 44, p. 2426 - 2437
  作者：Basnak,I.、Farkas,J.

  DOI：——

  日期：——
• BASNAK I.; FARKAS J., COLLECT. CZECH. CHEM. COMMUN., 1979, 44, NO 8, 2426-2437
  作者：BASNAK I.、 FARKAS J.

  DOI：——

  日期：——
• Synthesis and structure–activity relationships of a novel series of pyrimidines as potent inhibitors of TBK1/IKKε kinases
  作者：Edward G. McIver、Justin Bryans、Kristian Birchall、Jasveen Chugh、Thomas Drake、Stephen J. Lewis、Joanne Osborne、Ela Smiljanic-Hurley、William Tsang、Ahmad Kamal、Alison Levy、Michelle Newman、Debra Taylor、J. Simon C. Arthur、Kristopher Clark、Philip Cohen

  DOI：10.1016/j.bmcl.2012.09.063

  日期：2012.12

  The design, synthesis and structure-activity relationships of a novel series of 2,4-diamino-5-cyclopropyl pyrimidines is described. Starting from BX795, originally reported to be a potent inhibitor of PDK1, we have developed compounds with improved selectivity and drug-like properties. These compounds have been evaluated in a range of cellular and in vivo assays, enabling us to probe the putative role of the TBK1/IKK epsilon pathway in inflammatory diseases. (C) 2012 Elsevier Ltd. All rights reserved.