methyl (2E,4S)-4-(N-tert-butoxycarbonyl-N-hydroxymethyl)amino-5-phenylpent-2-enoate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl (2E,4S)-4-(N-tert-butoxycarbonyl-N-hydroxymethyl)amino-5-phenylpent-2-enoate
• 英文别名: methyl (E,4S)-4-[hydroxymethyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]-5-phenylpent-2-enoate
• 化学式: C₁₈H₂₅NO₅
• 分子量: 335.4
• InChiKey: FMGOIKVKYYHWHT-AUECHBEKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  76.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl (2E,4S)-4-(N-tert-butoxycarbonyl-N-hydroxymethyl)amino-5-phenylpent-2-enoate 在 甲醇 、 4-二甲氨基吡啶 、 重铬酸吡啶 、 5%-palladium/activated carbon 、 水 、 氢气 、 双氧水 、 magnesium sulfate 、 potassium carbonate 、 对甲苯磺酸 、 三乙胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 二氯甲烷 、 水 、 乙酸乙酯 为溶剂， 20.0 ℃ 、1.01 MPa 条件下， 反应 79.0h， 生成 (3R,4S)-4-(tert-butoxycarbonylamino)-3-hydroxy-5-phenylpentanoic acid
  参考文献：
  名称：

  Stereodivergent approach to both syn- and anti-isomers of γ-amino-β-hydroxy acids: (3S,4S)- and (3R,4S)-AHPPA derivatives

  摘要：

  A stereodivergent approach employing an N-hydroxymethyl group has been utilized to produce both diastereomeric derivatives of (3S,4S)-AHPPA 3 and (312,4S)-AHPPA 4, via an intramolecular conjugate addition and an intramolecular epoxidation, respectively. The selectivity of the intramolecular conjugate addition was more than 10:1 while that of the intramolecular epoxidation was more than 1:20. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.09.021
• 作为产物：
  描述：

  甲氧羰基亚甲基三苯基正膦 、 (4S)-4-benzyl-3-(tert-butoxycarbonyl)-5-hydroxyoxazolidine 以 苯 为溶剂， 反应 2.0h， 以94%的产率得到methyl (2E,4S)-4-(N-tert-butoxycarbonyl-N-hydroxymethyl)amino-5-phenylpent-2-enoate
  参考文献：
  名称：

  Stereodivergent approach to both syn- and anti-isomers of γ-amino-β-hydroxy acids: (3S,4S)- and (3R,4S)-AHPPA derivatives

  摘要：

  A stereodivergent approach employing an N-hydroxymethyl group has been utilized to produce both diastereomeric derivatives of (3S,4S)-AHPPA 3 and (312,4S)-AHPPA 4, via an intramolecular conjugate addition and an intramolecular epoxidation, respectively. The selectivity of the intramolecular conjugate addition was more than 10:1 while that of the intramolecular epoxidation was more than 1:20. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.09.021

文献信息

• Intramolecular Nucleophilic Epoxidation of γ-Amino-α,β-Unsaturated Esters with an<i>N</i>-Hydroperoxymethyl Group
  作者：Young Gyu Kim、Dongwon Yoo、Hyeonjeong Kim

  DOI：10.1055/s-2005-871558

  日期：——

  Intramolecular nucleophilic epoxidation reactions of γ-amino-α,β-unsaturated esters have been studied for the first time with a hydroperoxymethyl group attached to the nitrogen atom. The epoxidation was fast under mild basic conditions and highly anti selective (>20:1) when the alkyl group is small.

  首次研究了γ-氨基-α,β-不饱和酯的分子内亲核环氧化反应，其中氢过氧甲基与氮原子相连。环氧化在弱碱性条件下快速，当烷基较小时具有高抗选择性（>20:1）。
• Stereodivergent approach to both syn- and anti-isomers of γ-amino-β-hydroxy acids: (3S,4S)- and (3R,4S)-AHPPA derivatives
  作者：Dongwon Yoo、Jeeyun Song、Moon Sung Kang、Eun-Sil Kang、Young Gyu Kim

  DOI：10.1016/j.tetasy.2011.09.021

  日期：2011.9

  A stereodivergent approach employing an N-hydroxymethyl group has been utilized to produce both diastereomeric derivatives of (3S,4S)-AHPPA 3 and (312,4S)-AHPPA 4, via an intramolecular conjugate addition and an intramolecular epoxidation, respectively. The selectivity of the intramolecular conjugate addition was more than 10:1 while that of the intramolecular epoxidation was more than 1:20. (C) 2011 Elsevier Ltd. All rights reserved.