(S,S)-1,3-dimethyl-4,5-diphenylimidazolidin-2-one | 188299-19-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (S,S)-1,3-dimethyl-4,5-diphenylimidazolidin-2-one
• 英文别名: 2-Imidazolidinone, 1,3-dimethyl-4,5-diphenyl-, (4S,5S)-；(4S,5S)-1,3-dimethyl-4,5-diphenylimidazolidin-2-one
• CAS: 188299-19-6
• 化学式: C₁₇H₁₈N₂O
• 分子量: 266.343
• InChiKey: VDNQPGJZCBMFEH-HOTGVXAUSA-N

物化性质

• 沸点：
  411.4±45.0 °C(Predicted)
• 密度：
  1.130±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  23.6
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (S,S)-1,3-dimethyl-4,5-diphenylimidazolidin-2-one 在 草酰氯 、 氨 作用下， 以 甲醇 、 甲苯 、 乙腈 为溶剂， 生成 (4S,5S)-1,3-dimethyl-4,5-diphenyl-2-iminoimidazolidine
  参考文献：
  名称：

  Pentanidium 催化的对映选择性相转移共轭加成反应

  摘要：

  一种新的手性实体戊烷已被证明是一种出色的手性相转移催化剂。甘氨酸叔丁酯-二苯甲酮席夫碱与各种α,β-不饱和受体的对映选择性迈克尔加成反应提供了具有高对映选择性的加合物。在 0.05 mol% 的低催化剂负载下成功的克级实验表明该方法具有实际应用的潜力。磷酸甘氨酸酯类似物也可用作迈克尔供体，提供富含对映体的 α-氨基膦酸衍生物和 (S)-脯氨酸的膦酸类似物。

  DOI：

  10.1021/ja1098353
• 作为产物：
  描述：

  (4S,5S)-diphenylimidazolidin-2-one 、 碘甲烷 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 以2.1 g的产率得到(S,S)-1,3-dimethyl-4,5-diphenylimidazolidin-2-one
  参考文献：
  名称：

  Pentanidium 催化的对映选择性相转移共轭加成反应

  摘要：

  一种新的手性实体戊烷已被证明是一种出色的手性相转移催化剂。甘氨酸叔丁酯-二苯甲酮席夫碱与各种α,β-不饱和受体的对映选择性迈克尔加成反应提供了具有高对映选择性的加合物。在 0.05 mol% 的低催化剂负载下成功的克级实验表明该方法具有实际应用的潜力。磷酸甘氨酸酯类似物也可用作迈克尔供体，提供富含对映体的 α-氨基膦酸衍生物和 (S)-脯氨酸的膦酸类似物。

  DOI：

  10.1021/ja1098353

文献信息

• Guanidinium Ylide Mediated Aziridination:  Identification of a Spiro Imidazolidine-Oxazolidine Intermediate
  作者：Wannaporn Disadee、Tsutomu Ishikawa、Masatoshi Kawahata、Kentaro Yamaguchi

  DOI：10.1021/jo060531r

  日期：2006.8.1

  We successfully isolated a spiro imidazolidine-oxazolidine intermediate in the reaction of guanidinium ylide mediated aziridination using α-bromocinnamaldehyde. X-ray crystallographic analysis unambiguously revealed that the stereogenic centers of the spiro intermediate were in a trans configuration. The role of the spiro compound as an intermediate in the aziridination reaction was confirmed by observation

  我们成功地分离了螺亚胺唑烷-恶唑烷中间体，并利用α-溴肉桂醛在胍基内鎓盐介导的叠氮化反应中进行了反应。X射线晶体学分析清楚地表明，螺中间体的立体中心为反式构型。通过观察到螺环化合物顺利地化学转化成氮丙啶产物，证实了螺环化合物在叠氮反应中​​作为中间体的作用。
• [EN] NOVEL PHASE TRANSFER CATALYSTS<br/>[FR] NOUVEAUX CATALYSEURS DE TRANSFERT DE PHASE
  申请人：UNIV SINGAPORE

  公开号：WO2012057709A1

  公开（公告）日：2012-05-03

  Compounds of formula (I): wherein R1 to R8, and X- are defined herein. Also disclosed are methods of making and using these compounds.

  式（I）的化合物：其中R1至R8和X-在此定义。还公开了制备和使用这些化合物的方法。
• Chirality Transfer from Guanidinium Ylides to 3-Alkenyl (or 3-Alkynyl) Aziridine-2-carboxylates and Application to the Syntheses of (2<i>R</i>,3<i>S</i>)-3-Hydroxyleucinate and <scp>d</scp>-<i>e</i><i>rythro</i>-Sphingosine
  作者：Wannaporn Disadee、Tsutomu Ishikawa

  DOI：10.1021/jo051495j

  日期：2005.11.1

  Reaction of chiral guanidinium ylides with alpha,beta-unsaturated aldehydes gives 3-(alpha,beta-unsaturated) aziridine-2-carboxylates in high diastereo- and enantioselectivities (up to 93% diastereomeric excess and 98% enantiomeric excess). 3-(l-Methylvinyl)- and 3-[(E)-pentadec-1-enyllaziridine-2-carboxylates were successfully employed to prepare (2R,3S)-3-hydroxyleucinate and D-erythro-sphingosine, respectively.
• Simple preparation of chiral 1,3-dimethyl-2-iminoimidazolidines (monocyclic guanidines) and applications to asymmetric alkylative esterification
  作者：Toshio Isobe、Keiko Fukuda、Tsutomu Ishikawa

  DOI：10.1016/s0957-4166(98)00152-9

  日期：1998.5

  New chiral 1,3-dimethyl-2-iminoimidazolidines (monocyclic guanidines) were simply prepared by the action of primary amines on 2-chloro-1,3-dimethylimidazolinium chlorides, derived from the corresponding urea, in high yields. Modest asymmetric induction in alkylative esterification of benzoic acid with (1-bromoethyl)benzene was observed when the 1,3-dimethyl-4,5-diphenyl-2-[(1-phenyl-or 1-naphthyl)ethylimino]imidazolidines with all S (or R) configurations were used as bases. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Pentanidium–Catalyzed Enantioselective α-Hydroxylation of Oxindoles Using Molecular Oxygen
  作者：Yuanyong Yang、Farhana Moinodeen、Willy Chin、Ting Ma、Zhiyong Jiang、Choon-Hong Tan

  DOI：10.1021/ol302030v

  日期：2012.9.21

  Pentanidium-catalyzed alpha-hydroxylation of 3-substituted-2-oxindoles using molecular oxygen has been developed with good yields and enantioselectivities. This reaction does not require an additional reductant such as triethyl phosphite, which was typically added to reduce the peroxide intermediate. The reaction was demonstrated to consist of two-steps: an enantioselective formation of hydroperoxide oxindole and a kinetic resolution of the hydroperoxicle oxindole via reduction with enolates generated from the oxindoles.