(Z)-4-Benzyloxy-2-bromo-but-2-enoic acid ethyl ester | 552321-92-3

• 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: (Z)-4-Benzyloxy-2-bromo-but-2-enoic acid ethyl ester
• 英文别名: ethyl (Z)-2-bromo-4-phenylmethoxybut-2-enoate
• CAS: 552321-92-3
• 化学式: C₁₃H₁₅BrO₃
• 分子量: 299.164
• InChiKey: PBNVWHLKGUZATQ-WQLSENKSSA-N

物化性质

• 沸点：
  364.0±42.0 °C(Predicted)
• 密度：
  1.352±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (Z)-4-Benzyloxy-2-bromo-but-2-enoic acid ethyl ester 在 lithium aluminium tetrahydride 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.25h， 生成 (3S,4S,5S)-1-Allyl-4-benzyloxymethyl-5-hydroxymethyl-3-(toluene-4-sulfonyl)-pyrrolidin-2-one
  参考文献：
  名称：

  Formal Synthesis of (±)-Trachelanthamidine

  摘要：

  Base-induced coupling-cyclization stepwise [3+2] annulation of alpha-sulfonylacetamide with (Z)-2-bromoacrylate yielded the polysubstituted pyroglutarnate with three contiguous chiral centers with trans-trans orientation in a one-pot synthesis. The pyrrolizidine skeleton was obtained via the ring-closing metathesis (RCM) method. This facile strategy was used to synthesize (+/-)-trachelanthamidine.

  DOI：

  10.3987/com-05-10541
• 作为产物：
  描述：

  苯乙醛 、 ethyl 2-bromo-2-(triphenylphosphoranylidene)acetate 生成 (Z)-4-Benzyloxy-2-bromo-but-2-enoic acid ethyl ester
  参考文献：
  名称：

  Formal Synthesis of (±)-Trachelanthamidine

  摘要：

  Base-induced coupling-cyclization stepwise [3+2] annulation of alpha-sulfonylacetamide with (Z)-2-bromoacrylate yielded the polysubstituted pyroglutarnate with three contiguous chiral centers with trans-trans orientation in a one-pot synthesis. The pyrrolizidine skeleton was obtained via the ring-closing metathesis (RCM) method. This facile strategy was used to synthesize (+/-)-trachelanthamidine.

  DOI：

  10.3987/com-05-10541

文献信息

• A Facile Route to Polysubstituted<i> N</i>-Benzyl Pyroglutamates
  作者：Pei-Pei Sun、Meng-Yang Chang、Michael Y. Chiang、Nein-Chen Chang

  DOI：10.1021/ol0344164

  日期：2003.5.1

  [reaction: see text] Base-induced coupling/cyclization reactions of alpha-sulfonylacetamide with various ethyl (Z)-2-bromo-2-propenoates have been carried out. The polysubstituted pyroglutamate carbon skeleton, with three contiguous asymmetric centers, was built up in one step. A ring-closure mechanism is proposed for the reactions.

  [反应：见正文]已经进行了α-磺酰基乙酰胺与各种（Z）-2-溴-2-丙酸乙酯的碱诱导的偶联/环化反应。一步构建了具有三个连续不对称中心的多取代焦谷氨酸碳骨架。提出了反应的闭环机理。
• Formal Synthesis of (±)-Trachelanthamidine
  作者：Meng-Yang Chang、Dong-Ciao Wu、Nein-Chen Chang

  DOI：10.3987/com-05-10541

  日期：——

  Base-induced coupling-cyclization stepwise [3+2] annulation of alpha-sulfonylacetamide with (Z)-2-bromoacrylate yielded the polysubstituted pyroglutarnate with three contiguous chiral centers with trans-trans orientation in a one-pot synthesis. The pyrrolizidine skeleton was obtained via the ring-closing metathesis (RCM) method. This facile strategy was used to synthesize (+/-)-trachelanthamidine.