(2S,3R)-2-amino-3-(2-phenylethyl)pent-4-enoic acid | 749927-02-4

• 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: (2S,3R)-2-amino-3-(2-phenylethyl)pent-4-enoic acid
• CAS: 749927-02-4
• 化学式: C₁₃H₁₇NO₂
• 分子量: 219.283
• InChiKey: QLINBMWCYPBCJV-RYUDHWBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  63.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S,3R)-2-amino-3-(2-phenylethyl)pent-4-enoic acid 在 sodium carbonate 作用下， 以 1,4-二氧六环 、 乙醚 、 水 为溶剂， 生成 (2S,3R)-2-tert-Butoxycarbonylamino-3-phenethyl-pent-4-enoic acid methyl ester
  参考文献：
  名称：

  Synthesis of optically active β-alkyl aspartate via [3,3] sigmatropic rearrangement of α-acyloxytrialkylsilane

  摘要：

  The synthesis of four types of optically active beta-carbon-substituted analogs of threo-beta-hydroxy aspartate (THA) and a beta-carbon- substituted analog of threo-beta-benzyloxy aspartate (TBOA), which are potent blockers of excitatory amino acid transporters in the mammalian central nervous system, via the chirality-transferring ester-enolate Claisen rearrangement of alpha-acyloxytrialkylsilane is described. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.05.157
• 作为产物：
  描述：

  (E)-tert-butyldimethyl((5-phenylpent-2-en-1-yl)oxy)silane 在 zinc(II) chloride chromium(VI) oxide 、 4-二甲氨基吡啶 、 tetrafluoroboric acid 、 四甲基乙二胺 、 硫酸 、 仲丁基锂 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 (+)-二异松蒎基氯硼烷 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 、 丙酮 为溶剂， 反应 29.0h， 生成 (2S,3R)-2-amino-3-(2-phenylethyl)pent-4-enoic acid
  参考文献：
  名称：

  Synthesis of optically active β-alkyl aspartate via [3,3] sigmatropic rearrangement of α-acyloxytrialkylsilane

  摘要：

  The synthesis of four types of optically active beta-carbon-substituted analogs of threo-beta-hydroxy aspartate (THA) and a beta-carbon- substituted analog of threo-beta-benzyloxy aspartate (TBOA), which are potent blockers of excitatory amino acid transporters in the mammalian central nervous system, via the chirality-transferring ester-enolate Claisen rearrangement of alpha-acyloxytrialkylsilane is described. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.05.157

文献信息

• Synthesis of optically active β-alkyl aspartate via [3,3] sigmatropic rearrangement of α-acyloxytrialkylsilane
  作者：Kazuhiko Sakaguchi、Masahiro Yamamoto、Tetsuo Kawamoto、Takeshi Yamada、Tetsuro Shinada、Keiko Shimamoto、Yasufumi Ohfune

  DOI：10.1016/j.tetlet.2004.05.157

  日期：2004.7

  The synthesis of four types of optically active beta-carbon-substituted analogs of threo-beta-hydroxy aspartate (THA) and a beta-carbon- substituted analog of threo-beta-benzyloxy aspartate (TBOA), which are potent blockers of excitatory amino acid transporters in the mammalian central nervous system, via the chirality-transferring ester-enolate Claisen rearrangement of alpha-acyloxytrialkylsilane is described. (C) 2004 Elsevier Ltd. All rights reserved.