(2'R,4R,Z)-3-(4'-benzyloxyl-2'-allylbut-3'-enoyl)-4,5,5-triphenyloxazolidinone | 1393833-98-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (2'R,4R,Z)-3-(4'-benzyloxyl-2'-allylbut-3'-enoyl)-4,5,5-triphenyloxazolidinone
• 英文别名: (4R)-4,5,5-triphenyl-3-[(2R)-2-[(Z)-2-phenylmethoxyethenyl]pent-4-enoyl]-1,3-oxazolidin-2-one
• CAS: 1393833-98-1
• 化学式: C₃₅H₃₁NO₄
• 分子量: 529.635
• InChiKey: AXGIMUZABURFJF-AXTWEFHOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  40
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2'R,4R,Z)-3-(4'-benzyloxyl-2'-allylbut-3'-enoyl)-4,5,5-triphenyloxazolidinone 在 sodium tetrahydroborate 、 sodium chloride 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 16.0h， 以76%的产率得到
  参考文献：
  名称：

  ‘Syn-effect’ in the diastereoselective alkylation of 3-[(E)-α,β-unsaturated-γ-substituted]-N-acyloxazolidinones

  摘要：

  Synthetic methods for the formation of alkenes usually produce the E-alkene because it is more stable. However, in isomerization reaction (double bond migration) that takes place in alpha, beta-unsaturated carbonyl compounds, when these carbonyl compounds are exposed to strong bases, furnish Z-alkenes highly stereoselective depending on the gamma-substituent in the alpha, beta-unsaturated carbonyl. This stereo-selectivity can be attributed to the known Syn-effect. The synthetic value of this methodology is the achievement of chiral alcohol bearing an electron rich Z-alkene, as well as substituted, which was accomplished via removal of the oxazolidinone moiety under treatment with NaBH4, THF-H2O. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.05.037
• 作为产物：
  描述：

  ethyl 2E-4-(benzyloxy)-2-butenoate 在 三甲基乙酰氯 、 三乙胺 、 lithium chloride 、 lithium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 44.75h， 生成 (2'R,4R,Z)-3-(4'-benzyloxyl-2'-allylbut-3'-enoyl)-4,5,5-triphenyloxazolidinone
  参考文献：
  名称：

  ‘Syn-effect’ in the diastereoselective alkylation of 3-[(E)-α,β-unsaturated-γ-substituted]-N-acyloxazolidinones

  摘要：

  Synthetic methods for the formation of alkenes usually produce the E-alkene because it is more stable. However, in isomerization reaction (double bond migration) that takes place in alpha, beta-unsaturated carbonyl compounds, when these carbonyl compounds are exposed to strong bases, furnish Z-alkenes highly stereoselective depending on the gamma-substituent in the alpha, beta-unsaturated carbonyl. This stereo-selectivity can be attributed to the known Syn-effect. The synthetic value of this methodology is the achievement of chiral alcohol bearing an electron rich Z-alkene, as well as substituted, which was accomplished via removal of the oxazolidinone moiety under treatment with NaBH4, THF-H2O. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.05.037

文献信息

• Diastereoselective alkylations of oxazolidinone vinylogous glycolates
  作者：Jacqueline Jiménez、Rosa L. Meza-León、Fernando Sartillo-Piscil、Francisco J. Meléndez、Estibaliz Sansinenea、Aurelio Ortiz

  DOI：10.1016/j.tetlet.2012.06.133

  日期：2012.8

  A highly Z-selective isomerization (double bond migration) was observed when oxazolidinone vinylogous glycolate was exposed to a strong base to give N-acyl oxazolidinone, bearing an electron rich olefin. The corresponding enolate was exposed to alkyl halides to provide alkylated compounds on the gamma-position with respect to OBn group, with high regioselectivity and moderate diastereoselectivity. However, the nature of the chiral oxazolidinone leads to a significant increase in the reaction diastereoselectivity. A stereospecific formation of cis-olefin was also observed in these alkylated compounds. (c) 2012 Elsevier Ltd. All rights reserved.