α-Methylcrotonsaeurepiperidid | 54533-29-8

• 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: α-Methylcrotonsaeurepiperidid
• 英文别名: 1-(2-methyl-1-oxobut-2-enyl)piperidine；2-Buten-1-one, 2-methyl-1-(1-piperidinyl)-；(E)-2-methyl-1-piperidin-1-ylbut-2-en-1-one
• CAS: 54533-29-8
• 化学式: C₁₀H₁₇NO
• 分子量: 167.251
• InChiKey: AASUNBIGKXSKNF-YCRREMRBSA-N

物化性质

• 沸点：
  302.3±9.0 °C(Predicted)
• 密度：
  0.974±0.06 g/cm3(Predicted)
• LogP：
  1.562 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  哌啶 、 一氧化碳 、 (E)-crotyl methyl carbonate 在 十二羰基三钌 1,10-菲罗啉 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 100.0 ℃ 、4.05 MPa 条件下， 反应 10.0h， 以26%的产率得到(E)-1-(piperidin-1-yl)pent-3-en-1-one
  参考文献：
  名称：

  Ruthenium Complex-Catalyzed Carbonylation of Allylic Compounds

  摘要：

  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.

  DOI：

  10.1021/jo00104a036

文献信息

• HETEROCYCLIC COMPOUND
  申请人：Takeda Pharmaceutical Company Limited

  公开号：EP3287441A1

  公开（公告）日：2018-02-28

  The present invention relates to a compound which can be useful for the treatment or prevention of SPT-related diseases including cancer and congenital diseases associated with sphingolipid accumulation (including Niemann-Pick disease).

  本发明涉及一种化合物，该化合物可用于治疗或预防与 SPT 有关的疾病，包括癌症和与鞘脂蓄积有关的先天性疾病（包括尼曼-皮克病）。
• 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.