(4S,5R)-1,5-dimethyl-4-phenyl-3-prop-2-ynylimidazolidin-2-one | 943253-14-3

• 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,5R)-1,5-dimethyl-4-phenyl-3-prop-2-ynylimidazolidin-2-one
• CAS: 943253-14-3
• 化学式: C₁₄H₁₆N₂O
• 分子量: 228.294
• InChiKey: ULSUFAUJXBVHIM-DGCLKSJQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  23.6
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (4S,5R)-1,5-dimethyl-4-phenyl-3-prop-2-ynylimidazolidin-2-one 在 platinum on activated charcoal 、 Crabtree's catalyst sodium tetrahydroborate 、 potassium tert-butylate 、 氢气 、 sodium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 乙腈 为溶剂， 20.0~80.0 ℃ 、103.42 kPa 条件下， 反应 52.0h， 生成 (4R,5S)-1-[(2S,3S,6R)-6-[(2R)-1-[tert-butyl(diphenyl)silyl]oxypropan-2-yl]-3-methyloxan-2-yl]-3,4-dimethyl-5-phenylimidazolidin-2-one
  参考文献：
  名称：

  A Formal Total Synthesis of (+)-Zincophorin. Observation of an Unusual Urea-Directed Stork−Crabtree Hydrogenation

  摘要：

  A formal total synthesis of (+)-zincophorin via interception of Miyashita's advanced intermediates is described here. This effort features the first synthetic application of an inverse demand hetero [4 + 2] cycloaddition of a chiral allenamide, and the observation of an unusual urea directed Stork-Crabtree hydrogenation.

  DOI：

  10.1021/ol070791a
• 作为产物：
  描述：

  (4S,5R)-(+)-1,5-二甲基-4-苯基-2-咪唑啉酮 、 3-溴丙炔 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以98%的产率得到(4S,5R)-1,5-dimethyl-4-phenyl-3-prop-2-ynylimidazolidin-2-one
  参考文献：
  名称：

  Studies on a Urea-Directed Stork−Crabtree Hydrogenation. Synthesis of the C1−C9 Subunit of (+)-Zincophorin

  摘要：

  [GRAPHICS]A detailed account on the stereoselective synthesis of the C1-C9 subunit of (+)-zincophorin is described here. This approach features the first application of a stereoselective inverse electron demand hetero-[4 + 2] cycloaddition of chiral allenamides in natural product synthesis. The C1-C9 subunit matches Cossy's intermediate, thereby constituting a formal total synthesis. In addition, details of an unusual urea-directed Stork-Crabtree hydrogenation observed during these efforts are also disclosed here.

  DOI：

  10.1021/jo7017922

文献信息

• Studies on a Urea-Directed Stork−Crabtree Hydrogenation. Synthesis of the C1−C9 Subunit of (+)-Zincophorin
  作者：Zhenlei Song、Richard P. Hsung、Ting Lu、Andrew G. Lohse

  DOI：10.1021/jo7017922

  日期：2007.12.1

  [GRAPHICS]A detailed account on the stereoselective synthesis of the C1-C9 subunit of (+)-zincophorin is described here. This approach features the first application of a stereoselective inverse electron demand hetero-[4 + 2] cycloaddition of chiral allenamides in natural product synthesis. The C1-C9 subunit matches Cossy's intermediate, thereby constituting a formal total synthesis. In addition, details of an unusual urea-directed Stork-Crabtree hydrogenation observed during these efforts are also disclosed here.
• A Formal Total Synthesis of (+)-Zincophorin. Observation of an Unusual Urea-Directed Stork−Crabtree Hydrogenation
  作者：Zhenlei Song、Richard P. Hsung

  DOI：10.1021/ol070791a

  日期：2007.5.1

  A formal total synthesis of (+)-zincophorin via interception of Miyashita's advanced intermediates is described here. This effort features the first synthetic application of an inverse demand hetero [4 + 2] cycloaddition of a chiral allenamide, and the observation of an unusual urea directed Stork-Crabtree hydrogenation.