(4S)-3-(3-methyl-5-hexenoyl)-4-phenyl-2-oxazolidinone | 142078-06-6

• 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-(3-methyl-5-hexenoyl)-4-phenyl-2-oxazolidinone
• 英文别名: (4S)-3-[(3S)-3-methylhex-5-enoyl]-4-phenyl-1,3-oxazolidin-2-one
• CAS: 142078-06-6
• 化学式: C₁₆H₁₉NO₃
• 分子量: 273.332
• InChiKey: FFPRJVNQCKOWND-GXTWGEPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 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

• 作为产物：
  描述：

  氯丙烯镁 、 (4S)-N-crotonyl-4-phenyloxazolidin-2-one 在 copper(I) bromide dimethylsulfide complex 、 三氟化硼乙醚 作用下， 以 四氢呋喃 为溶剂， 以85%的产率得到(4S)-3-(3-methyl-5-hexenoyl)-4-phenyl-2-oxazolidinone
  参考文献：
  名称：

  有机铜试剂与N-烯酰恶唑烷酮的共轭加成中的非对映体选择

  摘要：

  据报道，对N-烯基-4-取代的恶唑烷酮类化合物中山本有机铜试剂的共轭加成进行了调查。具有相同相对构型的4-苯基和4-苄基恶唑烷酮的非对映选择性相反。链烯铜试剂在使用4-苯基恶唑烷酮辅助剂的不对称添加中显示出优异的结果。

  DOI：

  10.1016/s0040-4039(98)01966-2

文献信息

• Biogenetically Inspired Total Syntheses of<i>Lycopodium</i>Alkaloids, (+)-Flabellidine and (−)-Lycodine
  作者：Masayuki Azuma、Tetsuya Yoshikawa、Noriyuki Kogure、Mariko Kitajima、Hiromitsu Takayama

  DOI：10.1021/ja507016g

  日期：2014.8.20

  The first asymmetric total synthesis of (+)-flabellidine (2) and the shortest total synthesis of (-)-lycodine (3) were accomplished by a strategy featuring the one-pot construction of a tetracyclic lycodine skeleton from a linear precursor, which was inspired by the biosynthetic consideration of Lycopodium alkaloids.

  (+)-flabellidine (2) 的第一个不对称全合成和 (-)-lycodine 的最短全合成 (3) 是通过一种策略完成的，该策略的特点是从线性前体中一锅法构建四环 lycodine 骨架，其中灵感来自石松生物碱的生物合成考虑。
• Lewis acid promoted asymmetric 1,4-addition of allyltrimethylsilanes to chiral α,β-unsaturated n-acylamides
  作者：Ming-Jung Wu、Chi-Cheng Wu、Pei-Chen Lee

  DOI：10.1016/s0040-4039(00)92238-x

  日期：1992.4

  The 1,4-addition reaction of allyltrimethylsilane to alpha,beta-unsaturated N-acyloxazolidinones or N-enoyl-sultams in the presence of Lewis acid proceeds in good chemical yield with high diastereomeric excess. The absolute configuration of the new asymmetric center is controlled by the nature of the Lewis acid via transition state A or B.
• 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.