(2S,5S,1'R)-1-benzoyl-2-tert-butyl-5-methyl-3-(α-methylbenzyl)-1,3-imidazolidin-4-one | 170309-41-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2S,5S,1'R)-1-benzoyl-2-tert-butyl-5-methyl-3-(α-methylbenzyl)-1,3-imidazolidin-4-one
• 英文别名: (2R,5S)-1-benzoyl-2-tert-butyl-5-methyl-3-[(1R)-1-phenylethyl]imidazolidin-4-one
• CAS: 170309-41-8
• 化学式: C₂₃H₂₈N₂O₂
• 分子量: 364.488
• InChiKey: OKJXVRXXCLIPOW-JLHGSKIFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 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：

  (2S,5S,1'R)-1-benzoyl-2-tert-butyl-5-methyl-3-(α-methylbenzyl)-1,3-imidazolidin-4-one 在 正丁基锂 、 氯化铵 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以63%的产率得到(2S,5R,1'R)-1-benzoyl-2-tert-butyl-5-methyl-3-(α-methylbenzyl)-1,3-imidazolidin-4-one
  参考文献：
  名称：

  Highly Diastereoselective Alkylation of 1-Benzoyl-2-alkyl-3-(1'-methylbenzyl)imidazolidin-4-ones

  摘要：

  The synthetic utility of 2-alkyl-substituted 1,3-imidazolidinones for the enantioselective preparation of a-amino acids is now well documented in the literature. Incorporation of a N(3)-phenethyl group in these heterocycles leads to substantial enhancements in the diastereoselectivity of alkylation of the corresponding lithium enolates, so that stereoselectivities in the order of 19:1 to 49:1 are observed for 2-isopropyl and 2-tert-butyl derivatives, respectively. X-ray crystallographic analysis on five N(3)-phenethyl-substituted imidazolidinones provided evidence that the long-distance effect of that chiral moiety is the result of conformational changes provoked by steric interactions between the 2-alkyl and the N(3)-phenethyl groups. No additivity of the stereodirecting effects by the stereogenic centers at C(2) and C(1') was noticed, Thus, as it could have been anticipated from basic principles, intramolecular combinations of stereogenic centers do not necessarily lead to ''matched'' and ''mismatched'' joint stereoinducing effects.

  DOI：

  10.1021/jo00125a029
• 作为产物：
  描述：

  特戊醛 在 正丁基锂 、 三乙胺 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 12.0h， 生成 (2S,5S,1'R)-1-benzoyl-2-tert-butyl-5-methyl-3-(α-methylbenzyl)-1,3-imidazolidin-4-one
  参考文献：
  名称：

  Highly Diastereoselective Alkylation of 1-Benzoyl-2-alkyl-3-(1'-methylbenzyl)imidazolidin-4-ones

  摘要：

  The synthetic utility of 2-alkyl-substituted 1,3-imidazolidinones for the enantioselective preparation of a-amino acids is now well documented in the literature. Incorporation of a N(3)-phenethyl group in these heterocycles leads to substantial enhancements in the diastereoselectivity of alkylation of the corresponding lithium enolates, so that stereoselectivities in the order of 19:1 to 49:1 are observed for 2-isopropyl and 2-tert-butyl derivatives, respectively. X-ray crystallographic analysis on five N(3)-phenethyl-substituted imidazolidinones provided evidence that the long-distance effect of that chiral moiety is the result of conformational changes provoked by steric interactions between the 2-alkyl and the N(3)-phenethyl groups. No additivity of the stereodirecting effects by the stereogenic centers at C(2) and C(1') was noticed, Thus, as it could have been anticipated from basic principles, intramolecular combinations of stereogenic centers do not necessarily lead to ''matched'' and ''mismatched'' joint stereoinducing effects.

  DOI：

  10.1021/jo00125a029

文献信息

• Highly Diastereoselective Alkylation of 1-Benzoyl-2-alkyl-3-(1'-methylbenzyl)imidazolidin-4-ones
  作者：Eusebio Juaristi、Jose Luis Anzorena、Alois Boog、Domingo Madrigal、Dieter Seebach、Efren V. Garcia-Baez、Oscar Garcia-Barradas、Barbara Gordillo、A. Kramer

  DOI：10.1021/jo00125a029

  日期：1995.10

  The synthetic utility of 2-alkyl-substituted 1,3-imidazolidinones for the enantioselective preparation of a-amino acids is now well documented in the literature. Incorporation of a N(3)-phenethyl group in these heterocycles leads to substantial enhancements in the diastereoselectivity of alkylation of the corresponding lithium enolates, so that stereoselectivities in the order of 19:1 to 49:1 are observed for 2-isopropyl and 2-tert-butyl derivatives, respectively. X-ray crystallographic analysis on five N(3)-phenethyl-substituted imidazolidinones provided evidence that the long-distance effect of that chiral moiety is the result of conformational changes provoked by steric interactions between the 2-alkyl and the N(3)-phenethyl groups. No additivity of the stereodirecting effects by the stereogenic centers at C(2) and C(1') was noticed, Thus, as it could have been anticipated from basic principles, intramolecular combinations of stereogenic centers do not necessarily lead to ''matched'' and ''mismatched'' joint stereoinducing effects.