(4S)-3-((2R)-methyl-5-hexenoyl)-4-phenyl-2-oxazolidinone | 154499-37-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (4S)-3-((2R)-methyl-5-hexenoyl)-4-phenyl-2-oxazolidinone
• 英文别名: (4S)-3-<(2R)-methyl-5-hexenoyl>-4-phenyl-2-oxazolidinone；(S)-3-((R)-2-methylhex-5-enoyl)-4-phenyloxazolidin-2-one；(4S)-3-[(2R)-2-methylhex-5-enoyl]-4-phenyl-1,3-oxazolidin-2-one
• CAS: 154499-37-3
• 化学式: C₁₆H₁₉NO₃
• 分子量: 273.332
• InChiKey: MIDPQJOTBKSTIT-TZMCWYRMSA-N

物化性质

• 沸点：
  430.6±44.0 °C(predicted)
• 密度：
  1.135±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 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：

  (4S)-3-((2R)-methyl-5-hexenoyl)-4-phenyl-2-oxazolidinone 在 lithium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 2.0h， 以84%的产率得到(R)-2-methylhex-5-enoic acid
  参考文献：
  名称：

  Wu, Ming-Jung; Yeh, Jiann-Yih, Organic Preparations and Procedures International, 1994, vol. 26, # 6, p. 671 - 674

  摘要：

  DOI：
• 作为产物：
  描述：

  (4S)-3-(2-methyl-2-propenoyl)-4-phenyl-2-oxazolidinone 、 烯丙基三甲基硅烷 在 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以88%的产率得到(4S)-3-((2R)-methyl-5-hexenoyl)-4-phenyl-2-oxazolidinone
  参考文献：
  名称：

  Conjugate addition of allylsilanes to α,β-unsaturated N-acyloxazolidinones

  摘要：

  The conjugate addition of allyltrimethylsilane to alpha,beta-unsaturated N-acyloxazolidinone at -78 degrees C in the presence of TiCl4 gave the allylation product 3. However, when the reaction was carded out at room temperature, a small amount of cyclopentane adduct 4 was observed. The cyclopentane product formation can be prevented by employing BF3.OEt(2) as a Lewis acid. The enantioselective synthesis of optically pure 3-substituted-5-hexenoic acids was achieved by employing chiral oxazolidinone as a chiral auxiliary.

  DOI：

  10.1016/s0040-4020(01)80818-8

文献信息

• Total Synthesis of the Macrocyclic <i>N</i>-Methyl Enamides Palmyrolide A and 2<i>S</i>-Sanctolide A
  作者：Andrew D. Wadsworth、Daniel P. Furkert、Margaret A. Brimble

  DOI：10.1021/jo502238r

  日期：2014.11.21

  details of the total syntheses of the initially reported and revised structures of the neuroprotective agent palmyrolide A are reported. The key macrocyclization step was achieved using a sequential ring-closing metathesis/olefin isomerization reaction. Furthermore, the total synthesis of the related macrolide (2S)-sanctolide A is reported. The synthesis used key elements from the synthesis of palmyrolide

  报道了神经保护剂棕榈酰吡咯烷酮A的最初报道和修改的结构的全部合成的全部细节。关键的大环化步骤是使用顺序的闭环复分解/烯烃异构化反应实现的。此外，已经报道了相关的大环内酯（2S）-三萜内酯A的全合成。合成过程中使用了棕榈油酸酯A合成中的关键元素，包括RCM /烯烃异构化序列。本文所述的合成工作用于促进天然产物Sanctolide A的立体化学分配，并证明了该方法在合成大环叔烯酰胺天然产物中的效用。
• Conjugate addition of allylsilanes to α,β-unsaturated N-acyloxazolidinones
  作者：Ming-Jung Wu、Jiann-Yih Yeh

  DOI：10.1016/s0040-4020(01)80818-8

  日期：1994.1

  The conjugate addition of allyltrimethylsilane to alpha,beta-unsaturated N-acyloxazolidinone at -78 degrees C in the presence of TiCl4 gave the allylation product 3. However, when the reaction was carded out at room temperature, a small amount of cyclopentane adduct 4 was observed. The cyclopentane product formation can be prevented by employing BF3.OEt(2) as a Lewis acid. The enantioselective synthesis of optically pure 3-substituted-5-hexenoic acids was achieved by employing chiral oxazolidinone as a chiral auxiliary.
• Wu, Ming-Jung; Yeh, Jiann-Yih, Organic Preparations and Procedures International, 1994, vol. 26, # 6, p. 671 - 674
  作者：Wu, Ming-Jung、Yeh, Jiann-Yih

  DOI：——

  日期：——