methyl (2S)-4-methyl-2-[(2-methylpropan-2-yl)oxycarbonyl-prop-2-enylamino]pent-4-enoate | 954379-02-3

• 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)-4-methyl-2-[(2-methylpropan-2-yl)oxycarbonyl-prop-2-enylamino]pent-4-enoate
• CAS: 954379-02-3
• 化学式: C₁₅H₂₅NO₄
• 分子量: 283.368
• InChiKey: REFAVKDDAXHIOE-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 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)-4-methyl-2-[(2-methylpropan-2-yl)oxycarbonyl-prop-2-enylamino]pent-4-enoate 在 Grubbs catalyst first generation 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以97%的产率得到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
• 作为产物：
  描述：

  (2S,3S)-N-allyl-N-(tert-butoxycarbonyl)-3-amino-5-methyl-5-hexen-1,2-diol 在 2-甲基-2-丁烯 sodium chlorite 、 sodium periodate 、 sodium dihydrogenphosphate 、 碳酸氢钠 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 41.0h， 生成 methyl (2S)-4-methyl-2-[(2-methylpropan-2-yl)oxycarbonyl-prop-2-enylamino]pent-4-enoate
  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).