methyl (2S)-N-(tert-butoxycarbonyl)-1,2,3,6-tetrahydro-4-methylpyridine-2-carboxylate | 954379-03-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl (2S)-N-(tert-butoxycarbonyl)-1,2,3,6-tetrahydro-4-methylpyridine-2-carboxylate
• 英文别名: 1-O-tert-butyl 2-O-methyl (2S)-4-methyl-3,6-dihydro-2H-pyridine-1,2-dicarboxylate
• CAS: 954379-03-4
• 化学式: C₁₃H₂₁NO₄
• 分子量: 255.314
• InChiKey: IKZVRDUFADRMSQ-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (2S)-N-(tert-butoxycarbonyl)-1,2,3,6-tetrahydro-4-methylpyridine-2-carboxylate 在 platinum(IV) oxide 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 4.0h， 生成 methyl (2S,4S)-N-(tert-butoxycarbonyl)-4-methylpipecolate 、 methyl (-)-(2S,4R)-N-(tert-butoxycarbonyl)-4-methylpipecolate
  参考文献：
  名称：

  Enantioselective Synthesis of trans-4-Methylpipecolic Acid

  摘要：

  [GRAPHICS]An asymmetric synthesis for the preparation of both enantiomers of trans-methylpipecolic acids is described. It is based on Sharpless epoxidation as a chirality source, regioselective ring opening with allylamine, and ring-closing metathesis to construct the piperidine ring. The stereogenic center at C-4 is set by stereoselective hydrogenation that is directed by the alcohol functionality of an intermediate and proceeds with good diastereomeric control (trans/cis 16/1). Crystallization of the Boc-protected amino acid afforded the target products with excellent chemical (98% de) and enantiomeric purity (99% ee).

  DOI：

  10.1021/jo071220z
• 作为产物：
  描述：

  二碳酸二叔丁酯 在 Grubbs catalyst first generation 、 2-甲基-2-丁烯 、 lithium perchlorate sodium chlorite 、 sodium periodate 、 sodium dihydrogenphosphate 、 碳酸氢钠 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 乙腈 、 叔丁醇 为溶剂， 反应 85.0h， 生成 methyl (2S)-N-(tert-butoxycarbonyl)-1,2,3,6-tetrahydro-4-methylpyridine-2-carboxylate
  参考文献：
  名称：

  Enantioselective Synthesis of trans-4-Methylpipecolic Acid

  摘要：

  [GRAPHICS]An asymmetric synthesis for the preparation of both enantiomers of trans-methylpipecolic acids is described. It is based on Sharpless epoxidation as a chirality source, regioselective ring opening with allylamine, and ring-closing metathesis to construct the piperidine ring. The stereogenic center at C-4 is set by stereoselective hydrogenation that is directed by the alcohol functionality of an intermediate and proceeds with good diastereomeric control (trans/cis 16/1). Crystallization of the Boc-protected amino acid afforded the target products with excellent chemical (98% de) and enantiomeric purity (99% ee).

  DOI：

  10.1021/jo071220z

文献信息

• Enantioselective Synthesis of <i>trans</i>-4-Methylpipecolic Acid
  作者：Carlos Alegret、Ferran Santacana、Antoni Riera

  DOI：10.1021/jo071220z

  日期：2007.9.1

  [GRAPHICS]An asymmetric synthesis for the preparation of both enantiomers of trans-methylpipecolic acids is described. It is based on Sharpless epoxidation as a chirality source, regioselective ring opening with allylamine, and ring-closing metathesis to construct the piperidine ring. The stereogenic center at C-4 is set by stereoselective hydrogenation that is directed by the alcohol functionality of an intermediate and proceeds with good diastereomeric control (trans/cis 16/1). Crystallization of the Boc-protected amino acid afforded the target products with excellent chemical (98% de) and enantiomeric purity (99% ee).