2-甲基-1-哌啶子基-3-丁烯-1-酮 | 110961-74-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 中文名称: 2-甲基-1-哌啶子基-3-丁烯-1-酮
• 英文名称: 2-Methyl-1-piperidino-3-buten-1-one
• 英文别名: 2-Methyl-1-piperidin-1-ylbut-3-en-1-one
• CAS: 110961-74-5
• 化学式: C₁₀H₁₇NO
• 分子量: 167.251
• InChiKey: AVBDGTJCKCNNRB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  12
• 可旋转键数：
  2
• 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

• 作为反应物：
  描述：

  2-甲基-1-哌啶子基-3-丁烯-1-酮 在 lithium aluminium tetrahydride 、 lithium diisopropyl amide 作用下， 生成 (2R,3S)-5-Hydroxy-2,3-dimethyl-1-piperidin-1-yl-2-vinyl-pentan-1-one
  参考文献：
  名称：

  A stereoselective construction of the adjacent tertiary and quaternary carbons by the Michael addition

  摘要：

  DOI：

  10.1016/s0040-4039(00)95421-2
• 作为产物：
  描述：

  哌啶 以3%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

• Electrophile-Directed Diastereoselective Alkylation of Prochiral Enediolates
  作者：Stephen P. Marsden、Rebecca Newton

  DOI：10.1021/ja073624e

  日期：2007.10.1

  Prochiral substituted enediolates undergo diastereoselective alkylation with β-chiral primary iodohydrin derivatives, with selectivities up to 97:3. The most selective reactions occur with dienediolates, but reasonable selectivities can also be obtained with alkyl- and aryl-substituted enediolates. The presence of the lithioalkoxy substituent on the enolate is crucial for selectivity, as is the presence

  前手性取代的烯二醇与 β-手性伯碘醇衍生物进行非对映选择性烷基化，选择性高达 97:3。选择性最强的反应发生在二烯二醇酯上，但使用烷基和芳基取代的烯二醇酯也可以获得合理的选择性。烯醇化物上锂硫代烷氧基取代基的存在对选择性至关重要，正如亲电试剂中β-氧的存在一样，导致烷基化是通过亲核试剂和亲电试剂的锂配位组装发生的。该反应也适用于手性二级保护碘醇，从而有效构建连续的四级和三级不对称中心。
• 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.
• YAMAGUCHI MASAHIKO; HAMADA MICHIYUKI; NAKASHIMA HISATAKA; MINAMI TORU, TETRAHEDRON LETT., 28,(1987) N 16, 1785-1786
  作者：YAMAGUCHI MASAHIKO、 HAMADA MICHIYUKI、 NAKASHIMA HISATAKA、 MINAMI TORU

  DOI：——

  日期：——