(2R,5S)-2-(tert-butyl)-3,5-dimethylimidazolidin-4-one | 156592-72-2

• 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: (2R,5S)-2-(tert-butyl)-3,5-dimethylimidazolidin-4-one
• 英文别名: (2R,5S)-5-methyl-2-tert-butyl-3-methylimidazolidin-4-one；2-tert-Butyl-3,5-dimethyl-4-imidazolidinone, (2R,5S)-；(2R,5S)-2-tert-butyl-3,5-dimethylimidazolidin-4-one
• CAS: 156592-72-2
• 化学式: C₉H₁₈N₂O
• 分子量: 170.255
• InChiKey: MVEIZVYBCWRUDK-POYBYMJQSA-N

物化性质

• 沸点：
  264.2±33.0 °C(Predicted)
• 密度：
  0.953±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  32.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2R,5S)-2-(tert-butyl)-3,5-dimethylimidazolidin-4-one 在 N,N-二异丙基乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 60.75h， 生成 (2S,5S,5αR)-1-Benzoyl-2-tert-butyl-3,5-dimethyl-5-(α-methylbenzyl)imidazolidin-4-one
  参考文献：
  名称：

  New Amino Acids for the Topographical Control of Peptide Conformation: Synthesis of All the Isomers of .alpha.,.beta.-Dimethylphenylalanine and .alpha.,.beta.-Dimethyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylic Acid of High Optical Purity

  摘要：

  The synthesis of all four diastereoisomers of alpha,beta-dimethylphenylalanine (4) as well as those of alpha,beta-dimethyl-1 ,2,3,4,-tetrahydroisoquinoline-3-carboxylic acid (5 and 6) have been accomplished in high yield and high optical purity. Molecular mechanics calculations on the N-alpha-acetyl and N- methylcarboxamide derivatives of (3R,4R)-6 and (3R,4S)-5 indicate large and moderate energy stabilization for the gauche(-) but not the gauche(+) side-chain conformers of (3R,4S)-5 and (3R,4R)-6, respectively. By symmetry rules, the same holds for (3S,4R)-5 and (3S,4S)-6, respectively. Thus, these amino acids are potential building blocks for the topographical design of peptides (Kazmierski et al., J. Am. Chem. Sec. 1991, 113, 2275-2283) by providing acylated 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid derivatives in which a gauche(-) and not a gauche(+) side-chain conformation is energetically more stable for the L amino acid. Synthetic details and implications of these new amino acids for peptide and protein design are discussed.

  DOI：

  10.1021/jo00086a033
• 作为产物：
  描述：

  (S)-2-((2,2-dimethylpropylidene)amino)-N-methylpropanamide 在 乙酰氯 作用下， 以 乙醇 为溶剂， 反应 1.0h， 生成 (2R,5S)-2-(tert-butyl)-3,5-dimethylimidazolidin-4-one
  参考文献：
  名称：

  New Amino Acids for the Topographical Control of Peptide Conformation: Synthesis of All the Isomers of .alpha.,.beta.-Dimethylphenylalanine and .alpha.,.beta.-Dimethyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylic Acid of High Optical Purity

  摘要：

  The synthesis of all four diastereoisomers of alpha,beta-dimethylphenylalanine (4) as well as those of alpha,beta-dimethyl-1 ,2,3,4,-tetrahydroisoquinoline-3-carboxylic acid (5 and 6) have been accomplished in high yield and high optical purity. Molecular mechanics calculations on the N-alpha-acetyl and N- methylcarboxamide derivatives of (3R,4R)-6 and (3R,4S)-5 indicate large and moderate energy stabilization for the gauche(-) but not the gauche(+) side-chain conformers of (3R,4S)-5 and (3R,4R)-6, respectively. By symmetry rules, the same holds for (3S,4R)-5 and (3S,4S)-6, respectively. Thus, these amino acids are potential building blocks for the topographical design of peptides (Kazmierski et al., J. Am. Chem. Sec. 1991, 113, 2275-2283) by providing acylated 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid derivatives in which a gauche(-) and not a gauche(+) side-chain conformation is energetically more stable for the L amino acid. Synthetic details and implications of these new amino acids for peptide and protein design are discussed.

  DOI：

  10.1021/jo00086a033
• 作为试剂：
  描述：

  环己基乙醛 、 溴代丙二酸二乙酯 在 2,6-二甲基吡啶 、 (2R,5S)-2-(tert-butyl)-3,5-dimethylimidazolidin-4-one 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 diethyl 2-(1-cyclohexyl-2-oxoethyl)malonate
  参考文献：
  名称：

  Size-selective mesoporous silica-based Pt(II) complex as efficient and reusable photocatalytic material

  摘要：

  The grafting of a Pt(II) photocatalyst into three different mesoporous silica-based materials with different particle sizes and pore sizes was easily achieved through an amide bond formation. The analysis and results of the different characterization techniques showed that the catalyst is immobilized inside the pores of the materials and the photophysical properties of the catalyst are preserved after the covalent anchoring. The photocatalytic material catalyzed efficiently the debromination reaction of different substrates and is reused without detriment in its catalytic activity. In addition, the incorporation of the catalyst into mesoporous silica materials with different pore size allows the selective debromination of substrates by size discrimination. (C) 2019 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.jcat.2019.04.015

文献信息

• Herstellung enantiomerenreiner<i>cis</i>- oder<i>trans</i>-konfigurierter 2-(<i>tert</i>-Butyl)-3-methylimidazolidin-4-one aus den Aminosäuren (<i>S</i>)-Alanin, (<i>S</i>)-Phenylalanin, (<i>R</i>)-Phenylglycin, (<i>S</i>)-Methionin und (<i>S</i>)-Valin
  作者：Reto Naef、Dieter Seebach

  DOI：10.1002/hlca.19850680117

  日期：1985.2.13

  Preparation of the Enantiomerically Pure cis- and trans-Configurated 2-(tert-Butyl)-3-methylimidazolidin-4-ones from the Amino Acids (S)-Alanine, (S)-Phenylalanine, (R)-Phenylglycine, (S)-Methionine, and (S)-Valine

  对映体纯的制备顺式-和反式-构型的2-（叔丁基）-3-甲基咪唑烷-4-酮从氨基酸（小号） -丙氨酸，（小号） -苯丙氨酸，（- [R ）-苯基甘氨酸，（小号）-蛋氨酸和（S）-缬氨酸
• Tandem Addition/Cyclization of Alkynylzinc Reagents to Enantiopure 2-tert-Butyl-3,5-dimethyl-2,3-dihydroimidazol-4-oneN-Oxide: Potential Precursors of Quaternary α-Amino Acids
  作者：Frédéric Cantagrel、Sandra Pinet、Yves Gimbert、Pierre Y. Chavant

  DOI：10.1002/ejoc.200400861

  日期：2005.7

  A new enantiopure cyclic nitrone, a potential electrophilic alanine synthon, has been prepared. Its reaction with alkynylzinc reagents led to a tandem addition/cyclization reaction with complete regio- and stereoselectivity. The adducts are potential precursors of quaternary α-amino acids. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)

  一种新的对映体纯环硝酮，一种潜在的亲电子丙氨酸合成子，已被制备出来。它与炔基锌试剂的反应导致具有完全区域和立体选择性的串联加成/环化反应。加合物是季α-氨基酸的潜在前体。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)
• [EN] UNNATURAL AMINO ACIDS<br/>[FR] ACIDES AMINÉS NON NATURELS
  申请人：UNIV BRISTOL

  公开号：WO2018109496A3

  公开（公告）日：2018-07-26
• Preparation of the MacMillan imidazolidinones
  作者：Leopold Samulis、Nicholas C.O. Tomkinson

  DOI：10.1016/j.tet.2011.04.009

  日期：2011.6

  A general method for the preparation of the MacMillan imidazolidinones is described. Treatment of an alpha-amino amide with a carbonyl compound in refluxing chloroform in the presence of Yb(OTf)(3) (1 mol %) provides convenient access to the corresponding imidazolidinones. (C) 2011 Elsevier Ltd. All rights reserved.
• New Amino Acids for the Topographical Control of Peptide Conformation: Synthesis of All the Isomers of .alpha.,.beta.-Dimethylphenylalanine and .alpha.,.beta.-Dimethyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylic Acid of High Optical Purity
  作者：Wieslaw M. Kazmierski、Zofia Urbanczyk-Lipkowska、Victor J. Hruby

  DOI：10.1021/jo00086a033

  日期：1994.4

  The synthesis of all four diastereoisomers of alpha,beta-dimethylphenylalanine (4) as well as those of alpha,beta-dimethyl-1 ,2,3,4,-tetrahydroisoquinoline-3-carboxylic acid (5 and 6) have been accomplished in high yield and high optical purity. Molecular mechanics calculations on the N-alpha-acetyl and N- methylcarboxamide derivatives of (3R,4R)-6 and (3R,4S)-5 indicate large and moderate energy stabilization for the gauche(-) but not the gauche(+) side-chain conformers of (3R,4S)-5 and (3R,4R)-6, respectively. By symmetry rules, the same holds for (3S,4R)-5 and (3S,4S)-6, respectively. Thus, these amino acids are potential building blocks for the topographical design of peptides (Kazmierski et al., J. Am. Chem. Sec. 1991, 113, 2275-2283) by providing acylated 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid derivatives in which a gauche(-) and not a gauche(+) side-chain conformation is energetically more stable for the L amino acid. Synthetic details and implications of these new amino acids for peptide and protein design are discussed.