(E)-4-Phenyl-1-piperidino-3-buten-1-one | 76006-58-1

• 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: (E)-4-Phenyl-1-piperidino-3-buten-1-one
• 英文别名: 1-(4-phenyl-but-3-enoyl)-piperidine；1-(4-Phenyl-but-3-enoyl)-piperidin；(E)-4-phenyl-1-piperidin-1-ylbut-3-en-1-one
• CAS: 76006-58-1
• 化学式: C₁₅H₁₉NO
• 分子量: 229.322
• InChiKey: PUAOVCBUEBMQIC-JXMROGBWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (E)-4-Phenyl-1-piperidino-3-buten-1-one 、 silver trifluoromethanesulfonate 、 苯甲酰氯 生成 [(E)-4-phenyl-1-piperidin-1-ium-1-ylidenebut-3-enyl] benzoate;trifluoromethanesulfonate
  参考文献：
  名称：

  酰化叔酰胺。1-酰氧基亚胺盐和1-酰氧基亚胺的形成

  摘要：

  在三氟甲磺酸银的存在下，叔羧酰胺在氧原子上被苯甲酰基或乙酰氯酰化；如果所得的1-酰氧基亚胺盐在2或4位上含有氢原子，则可以将其脱质子化，以生成不稳定的1-酰氧基-烯胺或-二烯胺，它们已通过与4-苯基-1,2,4-三唑啉-反应而被捕集3，5-二酮。

  DOI：

  10.1039/c39800000790
• 作为产物：
  描述：

  哌啶 以57%的产率得到
  参考文献：
  名称：

  Mitsudo Take-aki, Suzuki Nobuyoshi, Kondo Teruyuki, Watanabe Yoshihisa, J. Org. Chem, 59 (1994) N 25, S 7759- 7765

  摘要：

  DOI：

文献信息

• Palladium-catalyzed carbonylation of allylamines via C–N bond activation leading to β,γ-unsaturated amides
  作者：Hui Yu、Guoying Zhang、Zong-Jian Liu、Hanmin Huang

  DOI：10.1039/c4ra13939a

  日期：——

  Pd(Xantphos)Cl₂ has been identified as an efficient catalyst for the direct carbonylation of allylamines via C–N bond activation.

  Pd（Xantphos）Cl₂已被确定为直接羰基化联烯胺的高效催化剂，通过C-N键活化实现。
• Ruthenium Complex-Catalyzed Carbonylation of Allylic Compounds
  作者：Take-aki Mitsudo、Nobuyoshi Suzuki、Teruyuki Kondo、Yoshihisa Watanabe

  DOI：10.1021/jo00104a036

  日期：1994.12

  Allylic alkyl carbonates are carbonylated under 40 atm of carbon monoxide at 100-120 degrees C in the presence of a catalytic amount of Ru-3(CO)(12)/1,10-phenanthroline to give alpha,beta- or beta,gamma-unsaturated esters in good to high yields. For example, cinnamyl methyl carbonate afforded the corresponding beta,gamma-unsaturated esters, methyl trans-4-phenyl-3-butenoate (1). in 93% yield. The regioselectivity in the carbonylation of crotyl methyl carbonate is unusual and it depends on the carbon monoxide pressure. The more sterically hindered carbon (gamma-carbon) is predominantly carbonylated at 20-50 atm. When the reaction of cinnamyl methyl carbonate was performed at elevated temperature (150 degrees C) without 1,10-phenanthroline, the dimer of 1, dimethyl 3-benzyl-2-(trans-2-phenylvinyl)glutarate, was obtained in 56% yield. In the presence of secondary amines, allylic alkyl carbonates were carbonylated mainly at alpha-carbon to give alpha,beta- or beta,gamma-unsaturated amides in high yields.
• Staudinger; Mueller, Chemische Berichte, 1923, vol. 56, p. 713
  作者：Staudinger、Mueller

  DOI：——

  日期：——
• BOTTOMLEY W. E.; BOYD G. V., J. CHEM. SOC. CHEM. COMMUN., 1980, NO 16, 790-791
  作者：BOTTOMLEY W. E.、 BOYD G. V.

  DOI：——

  日期：——
• Acylation of tertiary amides. Formation of 1-acyloxyiminium salts and 1-acyloxyenamines
  作者：William E. Bottomley、Gerhard V. Boyd

  DOI：10.1039/c39800000790

  日期：——

  Tertiary carboxamides are acylated at the oxygen atom by benzoyl or acetyl chloride in the presence of silver trifluoromethanesulphonate; if the resulting 1-acyloxyiminium salts contain hydrogen atoms at positions 2 or 4 they can be deprotonated to yield unstable 1-acyloxy-enamines or -dienamines, which have been trapped by reaction with 4-phenyl-1,2,4-triazoline-3,5-dione.

  在三氟甲磺酸银的存在下，叔羧酰胺在氧原子上被苯甲酰基或乙酰氯酰化；如果所得的1-酰氧基亚胺盐在2或4位上含有氢原子，则可以将其脱质子化，以生成不稳定的1-酰氧基-烯胺或-二烯胺，它们已通过与4-苯基-1,2,4-三唑啉-反应而被捕集3，5-二酮。