(4R,5S)-4-methyl-5-phenyl-3-((2E,4E)-1-oxo-2,4-hexadienyl)-2-oxazolidinone | 220944-25-2

• 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: (4R,5S)-4-methyl-5-phenyl-3-((2E,4E)-1-oxo-2,4-hexadienyl)-2-oxazolidinone
• 英文别名: (4R,5S)-3-[(2E,4E)-hexa-2,4-dienoyl]-4-methyl-5-phenyl-1,3-oxazolidin-2-one
• CAS: 220944-25-2
• 化学式: C₁₆H₁₇NO₃
• 分子量: 271.316
• InChiKey: RWSQIGQIUZDVDR-AXGREFEHSA-N

物化性质

• 沸点：
  390.2±45.0 °C(Predicted)
• 密度：
  1.149±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  (4R,5S)-4-methyl-5-phenyl-3-((2E,4E)-1-oxo-2,4-hexadienyl)-2-oxazolidinone 在 Grubbs catalyst first generation Bu3SnAlEt2 、 sodium hexamethyldisilazane 、 溶剂黄146 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 4.0h， 生成 (1S,2R,3R,6R,7E,9E,11R,12R,13E,17S)-2,11,12-trihydroxy-3-((S)-4-iodopent-4-en-2-yl)-6-methyl-4,20-dioxabicyclo[15.2.1]icosa-7,9,13-trien-5-one
  参考文献：
  名称：

  Total synthesis of amphidinolide E and amphidinolide E stereoisomers

  摘要：

  Four amphidinolide E stereoisomers, amphidinolide E (1), 2-epi-amphidinolide E (2), 19-epi-amphidinolide E (3), and 2-epi-19-epi- amphidinolide E (4), have been synthesized via the judicious union of aldehyde 5, allylsilanes 7 or 8, acids 9 or 10, and vinylstannane 6. The C19 stereocenters of the C19 epimeric allylsilanes 7 and 8 were introduced via crotylboration reactions early in the synthesis. [3+2] Annulation reactions of aldehyde 5 with allylsilanes 7 and 8 were employed to set the core tetrahydrofuran units of 1-4. Finally, the C2 stereo-center was installed by esterification using acid 9, without incident, or with acid 10, in which case an unexpected and completely stereoselective inversion of C2 occurs. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.02.058
• 作为产物：
  描述：

  (4R,5S)-(+)-4-甲基-5-苯基-2-恶唑啉酮 、 在 正丁基锂 作用下， 生成 (4R,5S)-4-methyl-5-phenyl-3-((2E,4E)-1-oxo-2,4-hexadienyl)-2-oxazolidinone
  参考文献：
  名称：

  区域和非对映选择性的硼介导的手性α，β，γ，δ-不饱和N-酰基恶唑烷酮的羟醛反应

  摘要：

  衍生自共轭二烯酸的手性N-酰基恶唑烷酮以高收率，高区域选择性和非对映选择性地进行硼介导的羟醛缩合，从而为引入1，3-二烯亚基提供了便利的方法。还描述了同源三烯衍生物的缩合。

  DOI：

  10.1016/s0957-4166(98)00459-5

文献信息

• Total Synthesis of Amphidinolide E
  作者：Porino Va、William R. Roush

  DOI：10.1021/ja066663j

  日期：2006.12.1

  A convergent and highly stereocontrolled synthesis of amphidinolide E (1) has been accomplished. The synthesis features a highly diastereoselective (>20:1) BF3.Et2O promoted [3+2] annulation reaction between aldehyde 3 and allylsilane 4 to afford substituted tetrahydrofuran 2.

  已经完成了amphidinolide E (1) 的聚合和高度立体控制的合成。该合成具有高度非对映选择性 (>20:1) BF3.Et2O 促进醛 3 和烯丙基硅烷 4 之间的 [3+2] 环化反应，得到取代的四氢呋喃 2。
• Iron-catalyzed enediene carbocyclizations. The total synthesis of (−)-gibboside
  作者：James M. Takacs、Suresh Vayalakkada、Steven J. Mehrman、Celia L. Kingsbury

  DOI：10.1016/s0040-4039(02)01662-3

  日期：2002.11

  The first total synthesis of (−)-gibboside is reported. The route features a novel iron-catalyzed carbocyclization as the key step for the construction of the cis,trans,cis-tetrasubstituted cyclopentane core.

  报告了（-）-糖苷的第一个全合成。该路线以新颖的铁催化的碳环化为特征，是构建顺，反，顺-四取代的环戊烷核心的关键步骤。
• Total synthesis of amphidinolide E and amphidinolide E stereoisomers
  作者：Porino Va、William R. Roush

  DOI：10.1016/j.tet.2007.02.058

  日期：2007.6

  Four amphidinolide E stereoisomers, amphidinolide E (1), 2-epi-amphidinolide E (2), 19-epi-amphidinolide E (3), and 2-epi-19-epi- amphidinolide E (4), have been synthesized via the judicious union of aldehyde 5, allylsilanes 7 or 8, acids 9 or 10, and vinylstannane 6. The C19 stereocenters of the C19 epimeric allylsilanes 7 and 8 were introduced via crotylboration reactions early in the synthesis. [3+2] Annulation reactions of aldehyde 5 with allylsilanes 7 and 8 were employed to set the core tetrahydrofuran units of 1-4. Finally, the C2 stereo-center was installed by esterification using acid 9, without incident, or with acid 10, in which case an unexpected and completely stereoselective inversion of C2 occurs. (C) 2007 Elsevier Ltd. All rights reserved.
• Regio- and diastereoselective boron-mediated aldol reactions of chiral α,β,γ,δ-unsaturated N-acyloxazolidinones
  作者：James M Takacs、Mohamad R Jaber、Benjamin J Swanson、Steven J Mehrman

  DOI：10.1016/s0957-4166(98)00459-5

  日期：1998.12

  Chiral N-acyloxazolidinones derived from conjugated dienoic acids undergo boron-mediated aldol condensation in good yield and with high regio- and diastereoselectivity to provide a convenient method for introducing a 1,3-diene subunit. The condensation of a homologous triene derivative is also described.

  衍生自共轭二烯酸的手性N-酰基恶唑烷酮以高收率，高区域选择性和非对映选择性地进行硼介导的羟醛缩合，从而为引入1，3-二烯亚基提供了便利的方法。还描述了同源三烯衍生物的缩合。