cis-2,4,5-triphenyl-2-imidazoline | 573-33-1

• 物质功能分类: 有机原料 - 杂环化合物
• 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: cis-2,4,5-triphenyl-2-imidazoline
• 英文别名: amarine；cis-2,4,5-triphenylimidazoline；(4S,5R)-2,4,5-triphenyl-4,5-dihydro-1H-imidazole
• CAS: 573-33-1
• 化学式: C₂₁H₁₈N₂
• 分子量: 298.387
• InChiKey: UCCFUHZMGXEALP-BGYRXZFFSA-N

物化性质

• 熔点：
  134.5°C
• 沸点：
  429.8°C (rough estimate)
• 密度：
  1.0750 (rough estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  24.4
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 海关编码：
  2933290090

反应信息

• 作为反应物：
  描述：

  cis-2,4,5-triphenyl-2-imidazoline 140.0~160.0 ℃ 、13.33 Pa 条件下， 以55%的产率得到2,4,5-三苯基咪唑
  参考文献：
  名称：

  闪蒸真空热解芳基甲基叠氮化物合成N，N-二（芳基亚甲基）芳基甲烷二胺

  摘要：

  闪蒸真空热解芳基甲基叠氮化物7a - d得到高产率（76-92％）的2,4-二氮杂戊二烯5a - d。的热环化5A - d得到顺-imidazolines 1A - d，进一步加热或Swern氧化1A - d给脱氢产物，咪唑2A - d。

  DOI：

  10.1016/j.tet.2004.06.082
• 作为产物：
  描述：

  三苯甲醛缩二胺 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 以90%的产率得到cis-2,4,5-triphenyl-2-imidazoline
  参考文献：
  名称：

  摘要：

  Novel data were obtained concerning the reaction of aromatic aldehydes with ammonia. A preparative method for the synthesis of new substituted 1,3,5-triaryl-2,4-diazapenta-1,4-dienes was developed. These products are the starting reactants for syntheses of cis- and trans-2,4,5-triaryl-2-imidazolines and 2,4,5-triarylimidazoles.

  DOI：

  10.1023/a:1023915024572

文献信息

• Substituted Dihydroimidazoles and their Use in the Treatment of Tumors
  申请人：Chamoin Sylvie

  公开号：US20100075966A1

  公开（公告）日：2010-03-25

  The invention relates to dihydroimidazoles of formula rac-(I), wherein the radicals and symbols are as defined herein; their use as inhibitors of the interaction of the MDM2 protein with a p53-like peptide, new pharmaceutical formulations comprising said compounds, said compounds for use in the therapeutic treatment of warm-blooded animals, especially humans, their use in the treatment of proliferative diseases or for the manufacture of pharmaceutical formulations useful in the treatment of proliferative diseases that respond to modulation of the interaction of the MDM2 protein with a p53-like peptide, a pharmaceutical formulation e.g. useful in the treatment of proliferative diseases that respond to modulation of the interaction of the MDM2 protein with a p53-like peptide comprising said compound, methods of treatment comprising administration of said compounds to a warm-blooded animal, and/or processes for the manufacture of said compounds.

  该发明涉及式rac-(I)的二氢咪唑，其中基团和符号如本文所定义；它们作为MDM2蛋白与类p53肽的相互作用抑制剂的用途，包括所述化合物的新药物配方，所述化合物用于治疗温血动物，特别是人类，它们用于治疗增殖性疾病或用于制造对MDM2蛋白与类p53肽相互作用调节有响应的药物配方，例如用于治疗对MDM2蛋白与类p53肽相互作用调节有响应的增殖性疾病的药物配方，包括所述化合物，包括所述化合物的治疗方法，包括将所述化合物用于温血动物的给药，和/或所述化合物的制造方法。
• Stereoselective synthesis of 1,2-diamino-1,2-diarylethane derivatives
  作者：I. V. Bessonov、N. A. Lozinskaya、V. R. Katashova、M. V. Proskurnina、N. S. Zefirov

  DOI：10.1007/s11172-005-0238-z

  日期：2005.1

  A procedure was developed for selective opening of the cis-2,4,5-triarylimidazoline ring to form erythro-1,2-diamino-1,2-diarylethane derivatives. These ring-opening products, erythro-ethylenediamine derivatives, can undergo quantitative isomerization to threo-ethylenediamine derivatives in the presence of strong bases in DMSO.

  开发了一种选择性打开 cis-2,4,5-三芳基咪唑啉环的方法，以形成 erythro-1,2-二氨基-1,2-二芳基乙烷衍生物。这些开环产物，即 erythro-乙二胺衍生物，可以在 DMSO 中在强碱的存在下发生定量异构化，生成 threo-乙二胺衍生物。
• Photochemical<i>cis-trans</i>Isomerization of 2,4,5-Triphenylimidazolines
  作者：Teruo Matsuura、Yoshikatsu Ito

  DOI：10.1246/bcsj.48.3669

  日期：1975.12

  Irradiation of cis- (amarine; I) and trans- (isoamarine; II) 2,4,5-triphenylimidazolines in acetonitrile or benzene gave a photostationary mixture of cis- and trans-isomers, the latter predominating over the former. On irradiation in a dilute acetone solution under the conditions that acetone absorbed most of the incident light, cis-trans isomerization occurred only with isoamarine but not with amarine

  在乙腈或苯中的顺式 (amarine; I) 和反式 (isoamarine; II) 2,4,5-三苯基咪唑啉的辐照得到顺式和反式异构体的光稳定混合物，后者优于前者。在丙酮吸收大部分入射光的条件下，在稀释的丙酮溶液中照射时，顺反异构化仅发生在异紫红素而不是紫红素。在丙酮中，也形成了 2,4,5-三苯基咪唑 (III)。提出了两种用于顺反异构化的中间体；咪唑啉基 IV 和/或 V 由丙酮的激发态（在丙酮中）夺氢形成，双自由基或两性离子物质 VIa 通过从 I 或 II 的激发态（在乙腈或苯中）裂解形成。提供了 VIa 中介的证据。
• Microwave-Assisted Rapid andSelective Synthesis of<i>cis</i>- and<i>trans</i>-2,4,5-Triarylimidazolinesfrom Aromatic Aldehydes
  作者：Takeshi Toru、Hitoshi Uchida、Hirofumi Tanikoshi、Shuichi Nakamura、Paidi Yella Reddy

  DOI：10.1055/s-2003-39906

  日期：——

  Microwave irradiation of a mixture of aromatic aldehydes and hexamethyldisilazane in the presence of a solid catalyst such as alumina afforded methanediamines which were efficiently converted to either cis- or trans-2,4,5-triarylimidazolines depending on the base used. A one-pot selective synthesis of cis- and transimidazolines from aromatic aldehydes was achieved under microwave irradiation.

  在固体催化剂（如氧化铝）存在下对芳香醛和六甲基二硅氮烷的混合物进行微波照射，得到甲二胺，根据所使用的碱，该甲二胺可有效转化为顺式或反式 2,4,5-三芳基咪唑啉。在微波辐射下实现了从芳香醛中一锅选择性合成顺式和反式咪唑啉。
• A Convenient Preparation of Enantiomerically Pure (+)-(1R,2R)- and (−)-(1S,2S)-1,2-Diamino-1,2-diphenylethanes
  作者：D. Christopher Braddock、Joanna M. Redmond、Stephen A. Hermitage、Andrew J. P. White

  DOI：10.1002/adsc.200505440

  日期：2006.5

  (1S,2S)-1 and (1R,2R)-1, is reported via (±)-iso-amarine 4. Strategically, the activation of (±)-iso-amarine 4 for hydrolysis to the required diamines and enantiomeric resolution is achieved simultaneously by formation of two separable diastereoisomeric N-acylamidines 5 and 6 derived from direct DCC-mediated coupling of (±)-iso-amarine 4 with (R)-acetylmandelic acid. iso-Amarine 4 is conveniently obtained

  （1 S，2 S）-和（1 R，2 R）-1,2-二氨基-1,2-二苯乙烷，（1 S，2 S）-1和（1 R，2 [R ）- 1，则报告经由- （±）异-amarine 4。在战略上，（±）激活-异-amarine 4为水解为所需的二胺和对映体拆分，通过形成的同时实现了两个可分离的非对映异构Ñ -acylamidines 5和6由DCC介导的（±）-异-amarine 4与（R）-乙酰扁桃酸的直接偶联得到。iso- Amarine 4是从Amarine 3方便地获得的，据报道，苯甲酸催化的苯甲醛和六甲基二硅氮烷的一锅合成。