3-trans-cinnamoyl-(4R)-diphenylmethyl-2-oxazolidinone

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-trans-cinnamoyl-(4R)-diphenylmethyl-2-oxazolidinone
• 英文别名: (4R)-4-benzhydryl-3-[(E)-3-phenylprop-2-enoyl]-1,3-oxazolidin-2-one
• 化学式: C₂₅H₂₁NO₃
• 分子量: 383.447
• InChiKey: LXIZFADVVAUGRW-QWYDYZLZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  3-trans-cinnamoyl-(4R)-diphenylmethyl-2-oxazolidinone 在 lithium hydroxide 、 三乙基硼 、 双氧水 、 氧气 、 三正丁基氢锡 、 ytterbium(III) triflate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 (S)-4-methyl-3-phenylpentanoic acid
  参考文献：
  名称：

  自由基介导的分子间共轭添加。路易斯酸、手性助剂和添加剂对非对映选择性的影响

  摘要：

  我们开发了一种高度非对映选择性的方法，用于使用 Bu3SnH 作为链载体和 Et3B/O2 作为自由基引发剂，将碳自由基共轭加成到手性 α,β-不饱和 N-烯酰基恶唑烷酮。路易斯酸已经过筛选，并且 Yb(OTf)3 证明在化学产率（1a 为 88%，1b 为 94%）和非对映选择性（1a 为 25:1，1b 为 46:1）方面均提供了优化结果。选择性取决于溶剂，CH2Cl2-THF 是理想的组合。不需要非常干燥的溶剂或反应条件。亚化学计量量的 Yb(OTf)3 提供了有效的反应，同时对非对映选择性的影响最小。具有合理亲核性的碳自由基通常是成功的，包括官能化自由基，如乙酰基或甲氧基甲基。亲电自由基不成功。

  DOI：

  10.1021/ja991205e

文献信息

• Stereoselective electrochemical carboxylation: 2-phenylsuccinates from chiral cinnamic acid derivatives
  作者：Monica Orsini、Marta Feroci、Giovanni Sotgiu、Achille Inesi

  DOI：10.1039/b500570a

  日期：——

  Chiral 2-phenyl succinic ester derivatives have been obtained under mild conditions, in short times and with satisfactory yields by electrochemical reduction of chiral cinnamic acid derivatives under a CO2 atmosphere. When 4R-(diphenylmethyl)-oxazolidin-2-one was used as a chiral auxiliary the two diastereoisomers could be easily separated by flash chromatography and the R-isomer was obtained as major product.

  通过在二氧化碳气氛下对手性肉桂酸衍生物进行电化学还原，在温和的条件下获得了手性 2-苯基琥珀酸酯衍生物，而且时间短、收率高。当使用 4R-（二苯基甲基）-噁唑烷-2-酮作为手性助剂时，两种非对映异构体很容易通过闪速色谱法分离，并获得 R-异构体作为主要产物。
• Enantioselective synthesis of peperomins A, C, D, and analogs — Examination of diastereoselective cuprate conjugate additions to <i>N</i>-enoyl-4-diphenylmethyl-2-oxazolidinones
  作者：Mukund P. Sibi、Michael D. Johnson、T. Punniyamurthy

  DOI：10.1139/cjc-79-11-1546

  日期：——

  A concise and general route to secolignans has been developed. The first total synthesis of secolignans peperomin A (1a), peperomin C (1b), and peperomin D (1c) was accomplished in similar to 28% overall yield over five synthetic steps. Peperomin analogs (1d) and (1e), possessing two differentially substituted aryl groups, were synthesized by a highly selective conjugate addition. The overall yield for the analogs 1d and 1e were 27 and 26%, respectively.
• Sibi, Mukund P.; Jasperse, Craig P.; Ji, Jianguo, Journal of the American Chemical Society, 1995, vol. 117, # 43, p. 10779 - 10780
  作者：Sibi, Mukund P.、Jasperse, Craig P.、Ji, Jianguo

  DOI：——

  日期：——
• Lewis acid mediated diastereoselective and enantioselective cyclopropanation of Michael acceptors with sulfur ylides
  作者：Ahmed Mamai、Jose S Madalengoitia

  DOI：10.1016/s0040-4039(00)01534-3

  日期：2000.11

  The reaction of N-enoyloxazolidinones with diphenylsulfonium isoproylide in the presence of Lewis acids is explored. The diastereoselectivity of the reaction of N-enoyloxazolidinones 1a and 1b with diphenylsulfonium isopropylide could be mediated by the addition of some Lewis acids. The reaction of N-enoyloxazolidinone 4 with diphenylsulfonium isoproylide was also explored with chiral Lewis acids. When this reaction was run with bis(oxazoline) ligand 6 and a number of Lewis acids, product was obtained in as high as 95% ee. A loss of stereoselectivity was observed with less than stoichiometric amounts of Lewis acid. (C) 2000 Published by Elsevier Science Ltd.
• A new chiral oxazolidinone derived from diphenylalaninol. Aldol, alkylation, and diels-alder reactions
  作者：Mukund P. Sibi、Prasad K. Deshpande、Jianguo Ji

  DOI：10.1016/0040-4039(95)01984-p

  日期：1995.12

  The chemistry of a new chiral oxazolidinone derived from D-diphenylalaninol is described. Aldol, alkylation, and Diets-Alder reactions using this auxiliary proceed in good chemical and excellent optical yields.