(4R,5S)-1,5-dimethyl-4-phenyl-3-[(3S)-3-phenylbutanoyl]imidazolidin-2-one | 113675-84-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: (4R,5S)-1,5-dimethyl-4-phenyl-3-[(3S)-3-phenylbutanoyl]imidazolidin-2-one
• CAS: 113675-84-6
• 化学式: C₂₁H₂₄N₂O₂
• 分子量: 336.434
• InChiKey: FBZSCSMNEZLCPU-FTRWYGJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (4R,5S)-1,5-dimethyl-4-phenyl-3-[(3S)-3-phenylbutanoyl]imidazolidin-2-one 在 lithium hydroxide 、 三氯化铝 、 草酰氯 作用下， 生成 (S)-3-methyl-1-indanone
  参考文献：
  名称：

  Preparation of chiral indanones and dihydrocoumarins; application to synthesis of (+)-3-(2,6-dimethoxyphenyl) pentanoic acid

  摘要：

  Chiral beta-aryl carboxylic acids, prepared by Michael addition of organocuprates to chiral unsaturated imides, are transformed into chiral 3-alkyl-4-benzoyloxyindan-1-ones via two intramolecular acylations, with intermediate formation of chiral 3-alkylindanones and corresponding dihydrocoumarins. The 3-(S)-ethyl-4-benzoyloxyindanone is transformed into(+)-3-(S)-(2,6-dimethoxyphenyl)pentanoic acid.

  DOI：

  10.1016/s0957-4166(00)80481-4
• 作为产物：
  描述：

  3-苯基-2-丙烯酰氯 在 2,3-二甲基苯胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 16.0h， 生成 (4R,5S)-1,5-dimethyl-4-phenyl-3-[(3S)-3-phenylbutanoyl]imidazolidin-2-one
  参考文献：
  名称：

  Additions diastéréosélectives d'alkyl, alcényl, aryl et allyl cuprates à des imides chirales insaturées

  摘要：

  Some diastereoselective conjugate additions of cuprates to chiral unsaturated imides hearing an imidazolidinyl group (from ephedrine and urea) show an impressive stereoselectivity. The chiral (internal auxiliary dependent) group is easily broken and recycled. The steric course of these reactions seems quite general and its development promising in synthesis.

  DOI：

  10.1016/s0040-4020(01)88188-6

文献信息

• Dibutylboron triflate promoted conjugate addition of benzylic and allylic organocopper reagents to chiral α,β-unsaturated N-acyl imidazolidinones
  作者：Pieter S. van Heerden、Barend C.B. Bezuidenhoudt、Daneel Ferreira

  DOI：10.1016/s0040-4039(97)00160-3

  日期：1997.3

  organocopper-Lewis acid system, RCu-TMEDA-Bu2BOTf, is useful for conjugate addition to highly constrained chiral α,β-unsaturated N-acyl imidazolidinones. In comparison with the corresponding TMSCl-activated reagents, Bu2BOTf exhibits a dramatic increase in reactivity during 1,4-addition of benzylic and allylic organocopper reagents, which react more readily with crotonoyl-, and especially cinnamoyl imides

  有机铜-路易斯酸体系RCu-TMEDA-Bu 2 BOTf可用于将共轭物添加到高度受限的手性α，β-不饱和N-酰基咪唑啉酮中。与相应的TMSC1活化的试剂相比，Bu 2 BOTf在苄基和烯丙基有机铜试剂的1，4-加成期间显示出显着的反应性，其更容易与巴豆酰基-尤其是肉桂酰基酰亚胺反应。
• Asymmetric 1,4 addition of grignard reagents to chiral α,β-unsaturated imides in the presence of lewis acids
  作者：Alessandro Bongini、Giuliana Cardillo、Anna Mingardi、Claudia Tomasini

  DOI：10.1016/0957-4166(96)00163-2

  日期：1996.5

  The asymmetric 1,4 addition of PhMgCl, MeMgBr and ally1MgBr to chiral imides 1 has been studied under various conditions. The presence of a Lewis acid, as AlMe(2)Cl, affords an enhanced diastereoselectivity favouring the formation of the product derived from the attack on the re face. The 1,4 addition of allyl diisopropoxyborate to imides 1 has also been analysed. Copyright (C) 1996 Elsevier Science Ltd