(4R)-3-cyclohexa-1,5-dien-1-yl-4-propan-2-yl-1,3-oxazolidin-2-one | 1453222-59-7

• 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)-3-cyclohexa-1,5-dien-1-yl-4-propan-2-yl-1,3-oxazolidin-2-one
• CAS: 1453222-59-7
• 化学式: C₁₂H₁₇NO₂
• 分子量: 207.272
• InChiKey: XMOUQVCZYSEELN-NSHDSACASA-N

物化性质

• 沸点：
  288.1±43.0 °C(predicted)
• 密度：
  1.125±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-戊烯-3-酮 、 (4R)-3-cyclohexa-1,5-dien-1-yl-4-propan-2-yl-1,3-oxazolidin-2-one 在 四氯化锡 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以76%的产率得到(R)-4-isopropyl-3-((1S,4S,5S)-5-propionylbicyclo[2.2.2]oct-2-en-2-yl)oxazolidin-2-one
  参考文献：
  名称：

  A Highly Stereoselective Diels–Alder Cycloaddition of Enones with Chiral Cyclic 2-Amidodienes Derived from Allenamides

  摘要：

  Lewis acid promoted Diels-Alder cycloadditions of a series of de novo chiral cyclic 2-amidodienes are described. These cyclic 2-amidodienes are derived from chiral alpha-allyl allenamides via a sequence of E-selective 1,3-H shift and 6 pi-electron pericyclic ring closure. With enones serving as effective dienophiles, these cycloadditions can be highly diastereoselective depending upon the chiral amide substituent, thereby representing a facile entry to optically enriched [2.2.2]bicyclic manifolds.

  DOI：

  10.1021/ol402254p

文献信息

• Stereoselective Synthesis of Isoquinuclidines through an Aza-[4 + 2] Cycloaddition of Chiral Cyclic 2-Amidodienes
  作者：Li-Chao Fang、Richard P. Hsung

  DOI：10.1021/ol500390a

  日期：2014.3.21

  A highly stereoselective aza-[4 + 2] cycloaddition of chiral cyclic 2-amidodienes with N-sulfonyl aldimines is described. While this Lewis acid promoted heterocycloaddition provides an efficient strategy for constructing optically enriched isoquinuclidines, it is mechanistically intriguing. The cycloaddition favored the endo-II pathway in the absence of a viable bidentate coordination. This represents

  描述了手性环状2-酰胺二烯与N-磺酰醛亚胺的高度立体选择性氮杂-[4+2]环加成。虽然这种路易斯酸促进的杂环加成为构建光学富集的异奎宁环提供了有效的策略，但它在机制上很有趣。在缺乏可行的二齿配位的情况下，环加成有利于内切 II途径。这代表了与全碳环加成中获得的预期内切 I选择性的意外转变。
• A Highly Stereoselective Diels–Alder Cycloaddition of Enones with Chiral Cyclic 2-Amidodienes Derived from Allenamides
  作者：Li-Chao Fang、Richard P. Hsung、Zhi-Xiong Ma、William R. Presser

  DOI：10.1021/ol402254p

  日期：2013.9.20

  Lewis acid promoted Diels-Alder cycloadditions of a series of de novo chiral cyclic 2-amidodienes are described. These cyclic 2-amidodienes are derived from chiral alpha-allyl allenamides via a sequence of E-selective 1,3-H shift and 6 pi-electron pericyclic ring closure. With enones serving as effective dienophiles, these cycloadditions can be highly diastereoselective depending upon the chiral amide substituent, thereby representing a facile entry to optically enriched [2.2.2]bicyclic manifolds.