1-(tert-butoxycarbonyl)-cis-2-methyl-6-n-undecylpiperidine | 132410-14-1

• 分子结构分类: 有机化合物 - 生物碱及其衍生物
• 英文名称: 1-(tert-butoxycarbonyl)-cis-2-methyl-6-n-undecylpiperidine
• 英文别名: tert-butyl (2S,6R)-2-methyl-6-undecylpiperidine-1-carboxylate
• CAS: 132410-14-1
• 化学式: C₂₂H₄₃NO₂
• 分子量: 353.589
• InChiKey: LUTKWGXFQQTXQE-VQTJNVASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8
• 重原子数：
  25
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(tert-butoxycarbonyl)-cis-2-methyl-6-n-undecylpiperidine 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以1.9 g的产率得到isosolenopsin A
  参考文献：
  名称：

  对映体纯净的火蚁毒生物碱的合成：脂溶菌素和异溶脂素A，B和C

  摘要：

  描述了一种简单有效的合成火蚁毒生物碱slenoppsin和isosolenopsin A，B和C对映异构体的方法。这些合成基于对映体纯的α-锂化的2-烷基哌啶的非对映选择性亲电取代。

  DOI：

  10.1002/jhet.5570450112
• 作为产物：
  描述：

  1-溴十一烷 在 palladium on activated charcoal 正丁基锂 、 氢气 、 lithium carbonate 、 sodium cyanoborohydride 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 9.0h， 生成 1-(tert-butoxycarbonyl)-cis-2-methyl-6-n-undecylpiperidine
  参考文献：
  名称：

  Stereocontrolled preparation of cis- and trans-2,6-dialkylpiperidines via 1-acyldihydropyridine intermediates. Synthesis of (.+-.)-solenopsin A and (.+-.)-dihydropinidine

  摘要：

  The stereoselective reduction of 1-(tert-butoxycarbonyl)-4-chloro-2,6-dialkyl-1,2-dihydropyridines 6 and 22 was studied. Reduction of 6 with Et3SiH/TFA gave the cis-2,6-dialkyl-1,2,5,6-tetrahydropyridine 7 as the major product. The stereoselectivity was reversed by reducing 6 with NaBH3CN/TFA, which gave predominantly the trans-2,6-dialkyltetrahydropyridine 10. Catalytic hydrogenation of 7 and 10 gave the corresponding N-Boc-cis(or trans)-2,6-dialkylpiperidines. Regioselective hydrogenation of 6 gave the 1,2,3,4-tetrahydropyridine 18, which on treatment with NaBH3CN/TFA provided a 90:10 mixture of trans- and cis-piperidines 15 and 16. More vigorous hydrogenation of 6 afforded the cis-piperidine 15 with 96% stereoselectivity. Similar stereoselective reductions of dihydropyridine 22 were carried out. Stereoselective reductions of dihydropyridines 6 and 22 were utilized in the synthesis of (+/-)-solenopsin A and (+/-)-dihydropinidine from 4-chloropyridine in six and five steps, respectively.

  DOI：

  10.1021/jo00007a044

文献信息

• Synthesis of enantiomerically pure fire ant venom alkaloids: Solenopsins and isosolenopsins A, B and C
  作者：H. M. T. Bandara Herath、N. P. Dhammika Nanayakkara

  DOI：10.1002/jhet.5570450112

  日期：2008.1

  Concise and efficient methods for the synthesis of enantiomers of fire ant venom alkaloids solenopsin and isosolenopsin A, B, and C are described. These syntheses are based on diastereoselective electrophilic substitution of enatiomerically-pure α-lithiated 2-alkylpiperidine.

  描述了一种简单有效的合成火蚁毒生物碱slenoppsin和isosolenopsin A，B和C对映异构体的方法。这些合成基于对映体纯的α-锂化的2-烷基哌啶的非对映选择性亲电取代。
• Stereocontrolled preparation of cis- and trans-2,6-dialkylpiperidines via 1-acyldihydropyridine intermediates. Synthesis of (.+-.)-solenopsin A and (.+-.)-dihydropinidine
  作者：Daniel L. Comins、Michael A. Weglarz

  DOI：10.1021/jo00007a044

  日期：1991.3

  The stereoselective reduction of 1-(tert-butoxycarbonyl)-4-chloro-2,6-dialkyl-1,2-dihydropyridines 6 and 22 was studied. Reduction of 6 with Et3SiH/TFA gave the cis-2,6-dialkyl-1,2,5,6-tetrahydropyridine 7 as the major product. The stereoselectivity was reversed by reducing 6 with NaBH3CN/TFA, which gave predominantly the trans-2,6-dialkyltetrahydropyridine 10. Catalytic hydrogenation of 7 and 10 gave the corresponding N-Boc-cis(or trans)-2,6-dialkylpiperidines. Regioselective hydrogenation of 6 gave the 1,2,3,4-tetrahydropyridine 18, which on treatment with NaBH3CN/TFA provided a 90:10 mixture of trans- and cis-piperidines 15 and 16. More vigorous hydrogenation of 6 afforded the cis-piperidine 15 with 96% stereoselectivity. Similar stereoselective reductions of dihydropyridine 22 were carried out. Stereoselective reductions of dihydropyridines 6 and 22 were utilized in the synthesis of (+/-)-solenopsin A and (+/-)-dihydropinidine from 4-chloropyridine in six and five steps, respectively.