(E)-(4S,5R)-4-methyl-3-(3'-phenyl-2'-propenoyl)-5-phenyl-2-oxazolidinone | 130272-30-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-(4S,5R)-4-methyl-3-(3'-phenyl-2'-propenoyl)-5-phenyl-2-oxazolidinone
• 英文别名: (4S,5R)-4-methyl-5-phenyl-3-[(E)-3-phenylprop-2-enoyl]-1,3-oxazolidin-2-one
• CAS: 130272-30-9
• 化学式: C₁₉H₁₇NO₃
• 分子量: 307.349
• InChiKey: GHIOEFKDVQJFHP-RMCBBKKWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 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：

  (E)-(4S,5R)-4-methyl-3-(3'-phenyl-2'-propenoyl)-5-phenyl-2-oxazolidinone 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 90.0h， 生成 2,5-Dimethyl-6-phenyl-cyclohex-3-enecarbothioic acid S-benzyl ester
  参考文献：
  名称：

  Cleavage of N-acyl oxazolidones

  摘要：

  DOI：

  10.1016/0040-4039(90)80164-h
• 作为产物：
  描述：

  去甲麻黄碱 在 四氯化锡 sodium hydride 、 sodium carbonate 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 20.0h， 生成 (E)-(4S,5R)-4-methyl-3-(3'-phenyl-2'-propenoyl)-5-phenyl-2-oxazolidinone
  参考文献：
  名称：

  (S)-4-Isopropyl-5,5-dimethyl-1,3-oxazolidinethione as chiral auxiliary for the intramolecular sulfur transfer in α,β-unsaturated N-acylimides, promoted by NbCl5

  摘要：

  The 1,3-oxazolidinethi one 4 has been synthesized from (S)-valine and used in the intramolecular sulfur transfer in its N-enoyl derivatives in the presence of NbCl5 as catalyst, which, moreover, works as an indicator of the course of the reaction. The adducts have subsequently been transformed into the corresponding beta-mercapto esters by action of Sm(OTf)(3) in methanol. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)02837-x

文献信息

• Stereoselective Conjugate Radical Additions:  Application of a Fluorous Oxazolidinone Chiral Auxiliary for Efficient Tin Removal
  作者：Jason E. Hein、Jake Zimmerman、Mukund P. Sibi、Philip G. Hultin

  DOI：10.1021/ol050956k

  日期：2005.6.1

  A series of asymmetric free-radical-mediated intermolecular conjugate additions using a fluorous oxazolidinone chiral auxiliary has been completed. The fluorous auxiliary facilitated product isolation using fluorous solid phase extractions (FSPE), effectively removing excess organic and organometallic reagents. Parallel reactions carried out with a similar but nonfluorous norephedrine-derived oxazoldinone demonstrated the superior stereoselectivity and purification obtainable with the fluorous chiral auxiliary.
• Enantioselective synthesis of dimethyl 3,4-diphenyladipate by electroreductive hydrocoupling of chiral N-trans-cinnamoyl-2-oxazolidones
  作者：Naoki Kise、Mitsuaki Echigo、Tatsuya Shono

  DOI：10.1016/s0040-4039(00)73190-x

  日期：1994.3

  Dimethyl(3R,4R)- and (3S,4S)-diphenyladipate were synthesized enantioselectively by electroreductive intermolecular hydrocoupling of chiral N-trans-cinnamoyl-2-oxazolidones and subsequent methanolysis.
• Stereoselective Hydrocoupling of Optically Active 3-<i>trans</i>-Cinnamoyloxazolidinones by Electroreduction
  作者：Naoki Kise、Syun-ichiro Mashiba、Nasuo Ueda

  DOI：10.1021/jo981231f

  日期：1998.10.1

  Reductive hydrocoupling of chiral 3-trans-cinnamoyloxazolidinones was studied by an electro chemical method. The electroreduction was performed conveniently at a constant current using an undivided cell. The stereoselectivity of the hydrodimers was strongly affected by the electrolyte employed. Electroreduction of (S)-4-isobutyl-3-trans-cinnamoyloxazolidinone 1a in 0.3 M Et4NOTs/AN gave a mixture of two diastereomers of all-trans cyclized hydrodimer 2a, and the selectivity was R,S,R/S,R,S = 85:15. On the other hand, the reduction of 1a in 1.7 M LiClO4/THF afforded a diastereomeric mixture of hydrodimers in a selectivity of R,R/S,S/R,S = 5:52:43. The stereoselectivities were explained by considering stable conformations of intermediate anion radicals, that is, syn-Z type for naked anion radicals and anti-Z type for lithiated anion radicals. Semiempirical calculations also supported this hypothesis. Electroreductions of (S)-4-isobutyl-3-cis-cinnamoyloxazolidinone and (S)-4-isobutyl-3-phenylpropioloyloxazolidinone gave 2a in the same stereoselectivity as electroreduction of 1a did. The electroreductive hydrocoupling was not inhibited by para and meta substitution on the aryl group of 3-trans-cinnamoyloxazolidinones. An ortho substitution, however, hindered the hydrocoupling and lowered the stereoselectivity of the hydrodimers. Electroreduction of 3-trans-cinnamoyloxazolidinethione and thiazolidinethione gave trans-3,4-diphenylcyclopentanone as a product, and the stereoselectivities were similar to that obtained from the corresponding oxazolidinone.
• Stereoselective coupling of optically active 3-trans-cinnamoyl-2-oxazolidinones with acid anhydrides by electroreduction
  作者：Naoki Kise、Yoshihiko Hirata、Takaaki Hamaguchi、Nasuo Ueda

  DOI：10.1016/s0040-4039(99)01720-7

  日期：1999.11

  The electronduction of chiral 3-trans-cinnamoyl-2-oxazolidinones with acid anhydrides gave beta-acylated products stereoselectively. The products were transformed to optically active cis-beta,gamma-disubstituted-gamma-lactones. (C) 1999 Elsevier Science Ltd. All rights reserved.