(R)-4-isopropyl-3-[(E)-(3-phenylacryloyl)]oxazolidin-2-one | 1240326-57-1

• 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: (R)-4-isopropyl-3-[(E)-(3-phenylacryloyl)]oxazolidin-2-one
• 英文别名: (R)-3-cinnamoyl-4-isopropyloxazolidin-2-one
• CAS: 1240326-57-1
• 化学式: C₁₅H₁₇NO₃
• 分子量: 259.305
• InChiKey: PNZYNDNOSVFRMU-XEHSLEBBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  46.61
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1-(苄氧基)-2-溴-4-甲基苯 、 (R)-4-isopropyl-3-[(E)-(3-phenylacryloyl)]oxazolidin-2-one 在 magnesium 、 copper(I) bromide 作用下， 以 四氢呋喃 为溶剂， 以23%的产率得到(R)-3-[(R)-3-(2-benzyloxy-5-methylphenyl)-3-phenylpropionyl]-4-isopropyloxazolidin-2-one
  参考文献：
  名称：

  Conjugate addition of aryl nucleophiles to α,β-unsaturated cinnamic acid derivatives containing Evans type chiral auxiliaries

  摘要：

  Cinnamides containing oxazolidin-2-one type auxiliaries have been prepared. A novel pathway to chiral 4-aryl-6-methyl-3,4-dihydrocoumrines via the asymmetric conjugate addition of arylmagnesium bromides to these cinnamides is described. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2016.07.003
• 作为产物：
  描述：

  肉桂酸 在 正丁基锂 、 氯化亚砜 作用下， 以 四氢呋喃 为溶剂， 反应 1.83h， 生成 (R)-4-isopropyl-3-[(E)-(3-phenylacryloyl)]oxazolidin-2-one
  参考文献：
  名称：

  Conjugate addition of aryl nucleophiles to α,β-unsaturated cinnamic acid derivatives containing Evans type chiral auxiliaries

  摘要：

  Cinnamides containing oxazolidin-2-one type auxiliaries have been prepared. A novel pathway to chiral 4-aryl-6-methyl-3,4-dihydrocoumrines via the asymmetric conjugate addition of arylmagnesium bromides to these cinnamides is described. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2016.07.003

文献信息

• <i>N</i>-Acylation of Oxazolidinones via Aerobic Oxidative NHC Catalysis
  作者：Linda Ta、Anton Axelsson、Henrik Sundén

  DOI：10.1021/acs.joc.8b01723

  日期：2018.10.5

  synthetically useful oxazolidinones with aldehydes using aerobic oxidative NHC catalysis is reported. The reaction offers a broad scope of functionalized oxazolidinones in good to excellent yields. Careful choice of electron transfer mediators proved pivotal to achieve efficient aerobic N-acylation, which has previously proven difficult using NHC catalysis. The methodology allows a mild entry to acylated oxazolidinones

  报道了使用好氧氧化NHC催化合成有用的恶唑烷酮与醛的第一个N-酰化反应。该反应以良好至优异的产率提供了广泛范围的官能化的恶唑烷酮。仔细选择电子传递介体被证明对实现有效的好氧N酰化至关重要，以前证明使用NHC催化是困难的。该方法允许温和地进入酰化的恶唑烷酮，避免使用危险的和反应性的预官能化底物。
• Electroreductive Coupling of Optically Active α,β-Unsaturated Carbonyl Compounds with Diaryl Ketones: Asymmetric Synthesis of 4,5,5-Trisubstituted γ-Butyrolactones
  作者：Naoki Kise、Yusuke Hamada、Toshihiko Sakurai

  DOI：10.1021/ol5013789

  日期：2014.6.20

  The electroreductive coupling of optically active N-E-crotonoyl- and N-cinnamoylimidazolidin-2-ones and oxazolidin-2-ones with diaryl ketones in the presence of chlorotrimethylsilane gave adducts with high diastereoselectivity. The adducts were readily transformed to optically active 4,5,5-trisubstituted γ-butyrolactones by treatment with TBAF.

  在氯代三甲基硅烷的存在下，光学活性的N - E-巴豆酰基-和N-肉桂酰咪唑烷-2-酮和恶唑烷-2-酮与二芳基酮的电还原偶联产生具有高非对映选择性的加合物。通过用TBAF处理，将加合物容易地转化为旋光的4,5,5-三取代的γ-丁内酯。