(4S)-1-phenyl-4-phenylmethyl-2-imidazolidinone | 195198-33-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (4S)-1-phenyl-4-phenylmethyl-2-imidazolidinone
• 英文别名: 2-Imidazolidinone, 1-phenyl-4-(phenylmethyl)-, (4S)-；(4S)-4-benzyl-1-phenylimidazolidin-2-one
• CAS: 195198-33-5
• 化学式: C₁₆H₁₆N₂O
• 分子量: 252.316
• InChiKey: CUEALDSWWAZCNP-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  32.3
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (4S)-1-phenyl-4-phenylmethyl-2-imidazolidinone 在 三氟甲磺酸二丁硼 、 potassium tert-butylate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.25h， 生成 (S)-4-Benzyl-3-((2S,3R)-3-hydroxy-2,4-dimethyl-pentanoyl)-1-phenyl-imidazolidin-2-one
  参考文献：
  名称：

  l-缬氨醇和l-苯丙氨醇衍生的2-咪唑啉酮作为不对称羟醛反应中的手性助剂

  摘要：

  从1-缬氨醇和1-苯丙氨醇分三步合成手性N-丙酰基-2-咪唑啉酮，其烯醇硼与醛的醛醇缩合反应以高非对映选择性进行。

  DOI：

  10.1016/s0040-4039(99)02325-4
• 作为产物：
  描述：

  (S)-N-[1-phenyl-3-(phenylamino)prop-2-yl]propionamide 在 sodium hydroxide 、 sodium hexamethyldisilazane 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 0.67h， 生成 (4S)-1-phenyl-4-phenylmethyl-2-imidazolidinone
  参考文献：
  名称：

  N-acylimidazolidin-2-ones: new chiral auxiliaries for carboxylic acid alkylation

  摘要：

  Chiral N-acylated imidazolidin-2-ones, readily available from aminoethanols in three steps through the nucleophilic opening of oxazoline intermediates, have been demonstrated to undergo highly diastereoselective benzylations and methylations via their sodium enolates. In most cases, the resulting products are highly crystalline, and the chiral auxiliaries can be readily recycled. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00255-3

文献信息

• Conformationally Programmable Chiral Foldamers with Compact and Extended Domains Controlled by Monomer Structure
  作者：Zachariah Lockhart、Peter C. Knipe

  DOI：10.1002/anie.201802822

  日期：2018.7.9

  Foldamers are an important class of abiotic macromolecules, with potential therapeutic applications in the disruption of protein–protein interactions. The majority adopt a single conformational motif such as a helix. A class of foldamer is now introduced where the choice of heterocycle within each monomer, coupled with a strong conformation‐determining dipole repulsion effect, allows both helical and

  折叠剂是一类重要的非生物大分子，在破坏蛋白质间相互作用方面具有潜在的治疗应用。大多数采用单个构象基序，例如螺旋。现在引入一类折叠剂，其中每个单体中杂环的选择以及强大的构象决定偶极排斥效应，可以选择螺旋构象和扩展构象。将这些单体结合成杂聚物，可以对构象空间进行高度受控的探索，并沿着多个载体投影侧链。折叠剂通过重复的脱保护-交叉偶联序列快速构建，并通过X射线晶体学，NMR和CD光谱分析了它们的固相和溶液相构象。
• Acid-mediated topological control in a functionalized foldamer
  作者：Peter C. Knipe、Sam Thompson、Andrew D. Hamilton

  DOI：10.1039/c6cc01496h

  日期：——

  Induced conformational change provides a powerful mechanism to modulate the structure and function of molecules. Here we describe the synthesis of chiral, surface-functionalized oligomeric pyridine/imidazolidin-2-one foldamers, and interrogate their acid-...

  诱导的构象变化提供了调节分子结构和功能的强大机制。在这里，我们描述了手性的，表面官能化的低聚吡啶/咪唑烷基-2-酮折叠剂的合成，并审问它们的酸-...
• Investigation of the Mitsunobu Reaction of<i>N</i>-(2-Hydroxyethyl)-<i>N′</i>-Phenyl-Ureas
  作者：Taek Hyeon Kim、Gue-Jae Lee、Mi-Hyun Cha

  DOI：10.1080/00397919908086441

  日期：1999.8

  The Mitsunobu reaction of N-(2-hydroxyethyl)-ureas 1 using PPh3 and EtO2CN=NCO2Et led to the mixture of N- and O-alkylation products or a single isomer depending on the substrates.
• Regiocontrolled Cyclization Reaction of <i>N</i>-(2-Hydroxyethyl)ureas by Transfer of Activation:  One-Pot Synthesis of 2-Imidazolidinones
  作者：Taek Hyeon Kim、Gue-Jae Lee

  DOI：10.1021/jo9820061

  日期：1999.4.1
• Diastereoselective alkylation of chiral 2-imidazolidinone glycolates: asymmetric synthesis of α-hydroxy carboxylic acids
  作者：Chong Chul Chun、Gue-Jae Lee、Jae Nyoung Kim、Taek Hyeon Kim

  DOI：10.1016/j.tetasy.2005.07.036

  日期：2005.9

  Sodium enolates of chiral 2-imidazolidinone glycolates reacted with alkyl halides to produce alpha-alkylated products with high diastereoselectivities, which were readily removed by simple alkaline hydrolysis and were converted to the protected alpha-hydroxy carboxylic acids. The new stereogenic center was assigned the (R) -configuration by comparison with known compounds. (C) 2005 Published by Elsevier Ltd.