cis-2,6-Diisobutylpiperidine | 198898-73-6

• 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: cis-2,6-Diisobutylpiperidine
• 英文别名: (2R,6S)-2,6-bis(2-methylpropyl)piperidine
• CAS: 198898-73-6
• 化学式: C₁₃H₂₇N
• 分子量: 197.364
• InChiKey: UMEAZVHLJSCGNV-BETUJISGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  环氧乙烷 、 cis-2,6-Diisobutylpiperidine 在 盐酸 作用下， 以80%的产率得到2-[(2R,6S)-2,6-bis(2-methylpropyl)piperidin-1-yl]ethanol
  参考文献：
  名称：

  Transformations of pyridine and deuteropyridine under the action of trimethallylborane and alcohols. Synthesis oftrans- andcis-2,6-dimethallyl-1,2,3,6-tetrahydropyridines and theirN-derivatives

  摘要：

  Reductive trans-2,6-dimethallylation of pyridine and deuteropyridine with trimethallylborane in the presence of alcohols proceeds at room temperature, i.e., under substantially milder conditions than the analogous reaction with the participation of triallylborane. trans-2,6-Di(2-methylallyl)-1 ,2,3,6-tetrahydropyridine (3) was obtained in a yield of 87%. When heated with trimethallylborane (130-135 degrees C, 2.5 h), compound 3 underwent isomerization to cis-2,6-di(2-methylallyl)-1,2,3,6-tetrahydropyridine (4). Hydrogenation of trans-(3) and cis-isomers (4) yielded trans-and cis-2,6-diisobutylpiperidines, respectively. The heterocycles obtained were N-functionalized by reactions with Mel, PhCH2Cl, ethylene oxide, and perfluoropropyloxirane. The stereochemistry of the cis-and trans-isomers (3 and 4) was established based on the NMR spectra of their N,N-dimethyl salts and the products of the reaction with ethylene oxide. trans-2,6-Dimethallyl-2,3,4,5,6-pentadeutero,2,3, 6-tetrahydropyridine and a number of its derivatives were prepared from the complex of trimethallylborane with C5D5N A probable mechanism of the reductive trans-2,6-diallylation of pyridines with allylboranes in the presence of alcohols is discussed.

  DOI：

  10.1007/bf02495933
• 作为产物：
  描述：

  (2S,6R)-2,6-bis(2-methylprop-2-enyl)-1,2,5,6-tetrahydropyridine 在 镍 甲醇 、 sodium hydroxide 、 氢气 、 tris(2-methyl-2-propenyl)borane 作用下， 以 溶剂黄146 为溶剂， 反应 13.5h， 生成 cis-2,6-Diisobutylpiperidine
  参考文献：
  名称：

  Transformations of pyridine and deuteropyridine under the action of trimethallylborane and alcohols. Synthesis oftrans- andcis-2,6-dimethallyl-1,2,3,6-tetrahydropyridines and theirN-derivatives

  摘要：

  Reductive trans-2,6-dimethallylation of pyridine and deuteropyridine with trimethallylborane in the presence of alcohols proceeds at room temperature, i.e., under substantially milder conditions than the analogous reaction with the participation of triallylborane. trans-2,6-Di(2-methylallyl)-1 ,2,3,6-tetrahydropyridine (3) was obtained in a yield of 87%. When heated with trimethallylborane (130-135 degrees C, 2.5 h), compound 3 underwent isomerization to cis-2,6-di(2-methylallyl)-1,2,3,6-tetrahydropyridine (4). Hydrogenation of trans-(3) and cis-isomers (4) yielded trans-and cis-2,6-diisobutylpiperidines, respectively. The heterocycles obtained were N-functionalized by reactions with Mel, PhCH2Cl, ethylene oxide, and perfluoropropyloxirane. The stereochemistry of the cis-and trans-isomers (3 and 4) was established based on the NMR spectra of their N,N-dimethyl salts and the products of the reaction with ethylene oxide. trans-2,6-Dimethallyl-2,3,4,5,6-pentadeutero,2,3, 6-tetrahydropyridine and a number of its derivatives were prepared from the complex of trimethallylborane with C5D5N A probable mechanism of the reductive trans-2,6-diallylation of pyridines with allylboranes in the presence of alcohols is discussed.

  DOI：

  10.1007/bf02495933

文献信息

• Transformations of pyridine and deuteropyridine under the action of trimethallylborane and alcohols. Synthesis oftrans- andcis-2,6-dimethallyl-1,2,3,6-tetrahydropyridines and theirN-derivatives
  作者：Yu. N. Bubnov、E. E. Demina、A. V. Ignatenko

  DOI：10.1007/bf02495933

  日期：1997.7

  Reductive trans-2,6-dimethallylation of pyridine and deuteropyridine with trimethallylborane in the presence of alcohols proceeds at room temperature, i.e., under substantially milder conditions than the analogous reaction with the participation of triallylborane. trans-2,6-Di(2-methylallyl)-1 ,2,3,6-tetrahydropyridine (3) was obtained in a yield of 87%. When heated with trimethallylborane (130-135 degrees C, 2.5 h), compound 3 underwent isomerization to cis-2,6-di(2-methylallyl)-1,2,3,6-tetrahydropyridine (4). Hydrogenation of trans-(3) and cis-isomers (4) yielded trans-and cis-2,6-diisobutylpiperidines, respectively. The heterocycles obtained were N-functionalized by reactions with Mel, PhCH2Cl, ethylene oxide, and perfluoropropyloxirane. The stereochemistry of the cis-and trans-isomers (3 and 4) was established based on the NMR spectra of their N,N-dimethyl salts and the products of the reaction with ethylene oxide. trans-2,6-Dimethallyl-2,3,4,5,6-pentadeutero,2,3, 6-tetrahydropyridine and a number of its derivatives were prepared from the complex of trimethallylborane with C5D5N A probable mechanism of the reductive trans-2,6-diallylation of pyridines with allylboranes in the presence of alcohols is discussed.