tert-butyl N-[(2S)-4-methyl-1-oxopent-4-en-2-yl]-N-prop-2-enylcarbamate | 954379-01-2

• 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: tert-butyl N-[(2S)-4-methyl-1-oxopent-4-en-2-yl]-N-prop-2-enylcarbamate
• CAS: 954379-01-2
• 化学式: C₁₄H₂₃NO₃
• 分子量: 253.342
• InChiKey: IJETYKLULXLFRL-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl N-[(2S)-4-methyl-1-oxopent-4-en-2-yl]-N-prop-2-enylcarbamate 在 platinum(IV) oxide 、 Grubbs catalyst first generation 、 2-甲基-2-丁烯 sodium chlorite 、 sodium dihydrogenphosphate 、 氢气 、 碳酸氢钠 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 46.0h， 生成 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：

  (2S,3S)-N-allyl-N-(tert-butoxycarbonyl)-3-amino-5-methyl-5-hexen-1,2-diol 在 sodium periodate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 5.0h， 生成 tert-butyl N-[(2S)-4-methyl-1-oxopent-4-en-2-yl]-N-prop-2-enylcarbamate
  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