1,1'-(1,4-phenylenebis(methylene))bis(piperidin-4-one)

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 1,1'-(1,4-phenylenebis(methylene))bis(piperidin-4-one)
• 英文别名: 1,1'-(1,4-phenylenebis(methylene))dipiperidin-4-one
• 化学式: C₁₈H₂₄N₂O₂
• 分子量: 300.401
• InChiKey: XEVODAWDJGWKLF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.02
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  40.62
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1,1'-(1,4-phenylenebis(methylene))bis(piperidin-4-one) 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 生成 1,1'-[1,4-phenylenebis(methylene)]dipiperidin-4-ol
  参考文献：
  名称：

  超声促进的新型两足和三脚哌啶-4-酮的合成，以及二氧化硅介导的向其哌啶-4-醇的转化：合成和结构限制。

  摘要：

  通过使4-哌啶酮盐酸盐一水合物与不同的烷基化剂和酰化剂反应，进行了超声促进的新型两足和三足哌啶蛋白-4-酮的合成。优选通过使用氯化硅的超声辐射将其还原为相应的哌啶-4-醇，其通过充当有效的载体聚合物而保持较高的产率。哌啶-4-酮的位阻邻苯二甲酰基衍生物是通过超声辐射合成的，这是常规方法难以做到的。

  DOI：

  10.1016/j.ultsonch.2011.10.018
• 作为产物：
  描述：

  1,4-二(溴甲基)苯 、 4-氧代哌啶酮盐酸盐 在 sodium carbonate 作用下， 以 乙腈 为溶剂， 反应 0.33h， 以92%的产率得到1,1'-(1,4-phenylenebis(methylene))bis(piperidin-4-one)
  参考文献：
  名称：

  超声促进的新型两足和三脚哌啶-4-酮的合成，以及二氧化硅介导的向其哌啶-4-醇的转化：合成和结构限制。

  摘要：

  通过使4-哌啶酮盐酸盐一水合物与不同的烷基化剂和酰化剂反应，进行了超声促进的新型两足和三足哌啶蛋白-4-酮的合成。优选通过使用氯化硅的超声辐射将其还原为相应的哌啶-4-醇，其通过充当有效的载体聚合物而保持较高的产率。哌啶-4-酮的位阻邻苯二甲酰基衍生物是通过超声辐射合成的，这是常规方法难以做到的。

  DOI：

  10.1016/j.ultsonch.2011.10.018

文献信息

• Polyaldol Synthesis by Direct Organocatalyzed Crossed Polymerization of Bis(ketones) and Bis(aldehydes)
  作者：Na Liu、Anthony Martin、Frédéric Robert、Jean-Marc Vincent、Yannick Landais、Joan Vignolle、Henri Cramail、Daniel Taton

  DOI：10.1021/ma402108y

  日期：2014.1.28

  Synthesis of polyaldols consisting of beta-keto alcohol monomer units is described. These polymers were obtained by direct step-growth polymerization of purposely designed bifunctional enolizable bis(ketone) monomers playing the role of nucleophilic donors, and activated nonenolizable bis(aldehyde)s serving as electrophilic acceptors. Monofunctional ketone and aldehyde homologues were first synthesized as models to establish the aldol reaction conditions using reaction partners at stoichiometry. A bifunctional organocatalytic system consisting of pyrrolidine in conjunction with acetic acid allowed performing polyaldolizations of stoichiometric amounts of the bis(aldehyde) and the bis(ketone) in solution in THF, DMSO, or DMF, at room temperature. However, polar solvents and/or prolonged reaction time induced further aldol reactions between aldol units of polymer chains, as indicated by the relatively broad molecular weight distribution of related polyaldols observed by size exclusion chromatography. Analysis by NMR spectroscopy confirmed the formation of beta-keto alcohol units, but also evidenced that the latter were also partly dehydrated into conjugated ketones via a crotonization reaction (from 20 to 33% depending on the structure of the initial monomers).