(S)-(+)-反式-5-苄氧基-4-氨基-2-戊烯酸乙酯 | 1006036-05-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (S)-(+)-反式-5-苄氧基-4-氨基-2-戊烯酸乙酯
• 英文名称: (S)-(+)-trans-5-benzyloxy-4-amino-2-pentenoic acid ethyl ester
• 英文别名: ethyl (E,4R)-4-amino-5-phenylmethoxypent-2-enoate
• CAS: 1006036-05-0
• 化学式: C₁₄H₁₉NO₃
• 分子量: 249.31
• InChiKey: IKRIVXUCXRKQST-MMQHEFTJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  61.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-(+)-反式-5-苄氧基-4-氨基-2-戊烯酸乙酯 在 N-羟基-7-氮杂苯并三氮唑 、 水 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 生成 ethyl (2S)-2-[(2R,3R,4S)-1-benzyl-5-oxo-4-(2-oxopropyl)-2-(phenylmethoxymethyl)pyrrolidin-3-yl]-2-hydroxyacetate
  参考文献：
  名称：

  Synthesis of densely functionalized pyrrolidinone templates by an intramolecular oxo-Diels–Alder reaction

  摘要：

  Preparation of densely functionalized pyrrolidinone templates, is a challenge for synthetic chemists. These templates are important building blocks for novel conformationally constrained natural products or for library generation of highly functionalized bi or polycyclic compounds. We discovered that trienes 6a-j undergo facile stereoselective intramolecular Diels-Alder reactions to generate densely functionalized cis fused pyrrolidinone templates 1a-j. These reactions allow for directed remote hydroxylation with complete control of stereochemistry. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)01711-2
• 作为产物：
  描述：

  Boc-O-苄基-L-丝氨酸-N，O-二甲基羟乙酰胺 在 lithium aluminium tetrahydride 、 potassium tert-butylate 、 三氟乙酸 作用下， 以 四氢呋喃 为溶剂， 生成 (S)-(+)-反式-5-苄氧基-4-氨基-2-戊烯酸乙酯
  参考文献：
  名称：

  Synthesis of densely functionalized pyrrolidinone templates by an intramolecular oxo-Diels–Alder reaction

  摘要：

  Preparation of densely functionalized pyrrolidinone templates, is a challenge for synthetic chemists. These templates are important building blocks for novel conformationally constrained natural products or for library generation of highly functionalized bi or polycyclic compounds. We discovered that trienes 6a-j undergo facile stereoselective intramolecular Diels-Alder reactions to generate densely functionalized cis fused pyrrolidinone templates 1a-j. These reactions allow for directed remote hydroxylation with complete control of stereochemistry. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)01711-2

文献信息

• Enantiomerically Pure α-Amino Aldehydes from Silylated α-Amino Acids
  作者：Buddy Soto-Cairoli、Jorge Justo de Pomar、John A. Soderquist

  DOI：10.1021/ol7028993

  日期：2008.1.1

  The disilylation of alpha-amino acids 1 to provide 2 (72-87%) was achieved without racemization. An unprecedented borane-mediated semi-reduction strategy was devised to convert 2 to stable, isolable oxazaborolidines 3 (100%) which were hydrolyzed to provide 5 (49-60%) as pure, stable compounds. Analysis of the Mosher amides (8) of the gamma-amino esters 7 reveals that <= 2% racemization occurs in the 1 -> 8 conversions.
• Synthesis of densely functionalized pyrrolidinone templates by an intramolecular oxo-Diels–Alder reaction
  作者：William V. Murray、Pranab K. Mishra、Sengen Sun、Amy Maden

  DOI：10.1016/s0040-4039(02)01711-2

  日期：2002.10

  Preparation of densely functionalized pyrrolidinone templates, is a challenge for synthetic chemists. These templates are important building blocks for novel conformationally constrained natural products or for library generation of highly functionalized bi or polycyclic compounds. We discovered that trienes 6a-j undergo facile stereoselective intramolecular Diels-Alder reactions to generate densely functionalized cis fused pyrrolidinone templates 1a-j. These reactions allow for directed remote hydroxylation with complete control of stereochemistry. (C) 2002 Elsevier Science Ltd. All rights reserved.