(2R,3R,6R)-3-methoxy-2-methyl-6-(pivaloyloxymethyl)piperidine | 874916-85-5

• 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: (2R,3R,6R)-3-methoxy-2-methyl-6-(pivaloyloxymethyl)piperidine
• 英文别名: [(2R,5R,6R)-5-methoxy-6-methylpiperidin-2-yl]methyl 2,2-dimethylpropanoate
• CAS: 874916-85-5
• 化学式: C₁₃H₂₅NO₃
• 分子量: 243.346
• InChiKey: NWIZNPIGVQZIGA-GMTAPVOTSA-N

物化性质

• 沸点：
  300.1±27.0 °C(Predicted)
• 密度：
  0.99±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,3R,6R)-3-methoxy-2-methyl-6-(pivaloyloxymethyl)piperidine 在 2,6-二甲基吡啶 、 正丁基锂 、 草酰氯 、 三氟甲磺酸三甲基硅酯 、 二异丁基氢化铝 、 二甲基亚砜 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 40.0h， 生成 (2R,3R,6R,1'E,3'E,5'E)-6-(deca-1',3',5'-trienyl)-3-methoxy-2-methylpiperidine
  参考文献：
  名称：

  Enantioselective total synthesis of (2R,3R,6R)-N-methyl-6-(deca-1′,3′,5′-trienyl)-3-methoxy-2-methylpiperidine, an insecticidal alkaloid

  摘要：

  An insecticidal piperidine alkaloid, (2R,3R,6R)-N-methyl-6-(deca-1',3',5-trienyl)-3-methoxy-2-methylpiperidine, was efficiently synthesized in a stereoselective manner starting from D-alanine. Chiral center at C-6 was controlled by hydrogenation of imine and side chain was introduced by Julia olefination. The absolute configuration of natural product was determined to be 2R, 3R, 6R. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.09.121
• 作为产物：
  描述：

  (5R,6R)-6-[(tert-butoxycarbonyl)amino]-5-methoxy-1-heptene 在 palladium on activated charcoal 吡啶 、 四氧化锇 、 重铬酸吡啶 、 4 A molecular sieve 、 氢气 、 N-甲基吗啉氧化物 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 丙酮 、 叔丁醇 为溶剂， 反应 27.67h， 生成 (2R,3R,6R)-3-methoxy-2-methyl-6-(pivaloyloxymethyl)piperidine
  参考文献：
  名称：

  Enantioselective total synthesis of (2R,3R,6R)-N-methyl-6-(deca-1′,3′,5′-trienyl)-3-methoxy-2-methylpiperidine, an insecticidal alkaloid

  摘要：

  An insecticidal piperidine alkaloid, (2R,3R,6R)-N-methyl-6-(deca-1',3',5-trienyl)-3-methoxy-2-methylpiperidine, was efficiently synthesized in a stereoselective manner starting from D-alanine. Chiral center at C-6 was controlled by hydrogenation of imine and side chain was introduced by Julia olefination. The absolute configuration of natural product was determined to be 2R, 3R, 6R. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.09.121

文献信息

• Enantioselective total synthesis of (2R,3R,6R)-N-methyl-6-(deca-1′,3′,5′-trienyl)-3-methoxy-2-methylpiperidine, an insecticidal alkaloid
  作者：Yusuke Nakatani、Jun Oshita、Ken Ishigami、Hidenori Watanabe、Takeshi Kitahara

  DOI：10.1016/j.tet.2005.09.121

  日期：2006.1

  An insecticidal piperidine alkaloid, (2R,3R,6R)-N-methyl-6-(deca-1',3',5-trienyl)-3-methoxy-2-methylpiperidine, was efficiently synthesized in a stereoselective manner starting from D-alanine. Chiral center at C-6 was controlled by hydrogenation of imine and side chain was introduced by Julia olefination. The absolute configuration of natural product was determined to be 2R, 3R, 6R. (c) 2005 Elsevier Ltd. All rights reserved.