Ethyl 2-[4-(4-phenylbut-3-en-2-yl)piperazin-1-yl]pyrimidine-5-carboxylate | 875138-60-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: Ethyl 2-[4-(4-phenylbut-3-en-2-yl)piperazin-1-yl]pyrimidine-5-carboxylate
• 英文别名: ethyl 2-[4-(4-phenylbut-3-en-2-yl)piperazin-1-yl]pyrimidine-5-carboxylate
• CAS: 875138-60-6
• 化学式: C₂₁H₂₆N₄O₂
• 分子量: 366.463
• InChiKey: XBGHQDFMYPESPP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  58.6
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  O-(四氢-2H-吡喃-2-基)羟基胺 、 Ethyl 2-[4-(4-phenylbut-3-en-2-yl)piperazin-1-yl]pyrimidine-5-carboxylate 在 水 、 sodium hydroxide 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三乙胺 作用下， 以 乙醇 、 四氢呋喃 、 二氯甲烷 为溶剂， 以70%的产率得到N-(oxan-2-yloxy)-2-[4-(4-phenylbut-3-en-2-yl)piperazin-1-yl]pyrimidine-5-carboxamide
  参考文献：
  名称：

  Identification of a series of substituted 2-piperazinyl-5-pyrimidylhydroxamic acids as potent histone deacetylase inhibitors

  摘要：

  Pursuing our efforts in designing 5-pyrimidylhydroxamic acid anti-cancer agents, we have identified a new series of potent histone deacetylase (HDAC) inhibitors. These compounds exhibit enzymatic HDAC inhibiting properties with IC50 values in the nanomolar range and inhibit tumor cell proliferation at similar levels. Good solubility, moderate bioavailability, and promising in vivo activity in xenograft model made this series of compounds interesting starting points to design new potent HDAC inhibitors. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.10.118
• 作为产物：
  描述：

  2-(哌嗪-1-基)嘧啶-5-羧酸乙酯 、 苄叉丙酮 在 titanium(IV) tetraethanolate 作用下， 以 1,2-二氯乙烷 为溶剂， 以8%的产率得到Ethyl 2-[4-(4-phenylbut-3-en-2-yl)piperazin-1-yl]pyrimidine-5-carboxylate
  参考文献：
  名称：

  Identification of a series of substituted 2-piperazinyl-5-pyrimidylhydroxamic acids as potent histone deacetylase inhibitors

  摘要：

  Pursuing our efforts in designing 5-pyrimidylhydroxamic acid anti-cancer agents, we have identified a new series of potent histone deacetylase (HDAC) inhibitors. These compounds exhibit enzymatic HDAC inhibiting properties with IC50 values in the nanomolar range and inhibit tumor cell proliferation at similar levels. Good solubility, moderate bioavailability, and promising in vivo activity in xenograft model made this series of compounds interesting starting points to design new potent HDAC inhibitors. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.10.118

文献信息

• Asymmetric intermolecular allylic C–H amination of alkenes with aliphatic amines
  作者：Kelvin Pak Shing Cheung、Jian Fang、Kallol Mukherjee、Andranik Mihranyan、Vladimir Gevorgyan

  DOI：10.1126/science.abq1274

  日期：2022.12.16

  Aliphatic allylic amines are found in a great variety of complex and biorelevant molecules. The direct allylic C–H amination of alkenes serves as the most straightforward method toward these motifs. However, use of widely available internal alkenes with aliphatic amines in this transformation remains a synthetic challenge. In particular, palladium catalysis faces the twin challenges of inefficient

  脂肪族烯丙胺存在于多种复杂的生物相关分子中。烯烃的直接烯丙基 C-H 胺化是实现这些基序的最直接方法。然而，在这种转化中使用广泛使用的内烯烃和脂肪胺仍然是一个合成挑战。特别是，钯催化面临着双重挑战：Pd(II) 与内部烯烃的配位效率低下，但由于碱性脂肪胺对 Pd(II) 的配位过于紧密，因此抑制配位。我们报告了这些问题的通用解决方案。与经典的 Pd(II/0) 方案相比，所开发的方案通过蓝光诱导的 Pd(0/I/II) 歧管与温和的芳基溴氧化剂进行操作。这种开壳方法还可以实现对映和非对映选择性烯丙基 C-H 胺化。