(Z)-5-(2-ethoxybenzylidene)imidazolidine-2,4-dione

• 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: (Z)-5-(2-ethoxybenzylidene)imidazolidine-2,4-dione
• 英文别名: 5-[1-(2-Ethoxy-phenyl)-meth-(Z)-ylidene]-imidazolidine-2,4-dione；(5Z)-5-[(2-ethoxyphenyl)methylidene]imidazolidine-2,4-dione
• 化学式: C₁₂H₁₂N₂O₃
• 分子量: 232.239
• InChiKey: HEVMPJZRFSDLON-CLFYSBASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  67.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (Z)-5-(2-ethoxybenzylidene)imidazolidine-2,4-dione 在 (11bS)-4-羟基-2,6-二[2,4,6-三(异丙基)苯基]-二萘并[2,1-d:1',2'-f][1,3,2]二氧杂磷杂卓4-氧化物 、 palladium(II) trifluoroacetate 、 氢气 、 (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl 作用下， 以 2,2,2-三氟乙醇 为溶剂， 70.0 ℃ 、4.05 MPa 条件下， 反应 24.0h， 以56%的产率得到
  参考文献：
  名称：

  Synthesis of chiral hydantoin derivatives by homogeneous Pd-catalyzed asymmetric hydrogenation

  摘要：

  5-Aryl substituted chiral hydantoin derivatives were synthesized via asymmetric hydrogenation of prochiral exocyclic alkenes using a Pd/BINAP catalyst. Moderate to good enantioselectivity were obtained (21-90% ee). A chiral Bronsted acid additive was found to be a key factor to obtain high enantioselectivity. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2016.10.006
• 作为产物：
  描述：

  海因 、 2-乙氧基苯甲醛 在 C.I.酸性橙108 作用下， 以 乙醇 、 水 为溶剂， 反应 24.0h， 以81%的产率得到(Z)-5-(2-ethoxybenzylidene)imidazolidine-2,4-dione
  参考文献：
  名称：

  Synthesis of chiral hydantoin derivatives by homogeneous Pd-catalyzed asymmetric hydrogenation

  摘要：

  5-Aryl substituted chiral hydantoin derivatives were synthesized via asymmetric hydrogenation of prochiral exocyclic alkenes using a Pd/BINAP catalyst. Moderate to good enantioselectivity were obtained (21-90% ee). A chiral Bronsted acid additive was found to be a key factor to obtain high enantioselectivity. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2016.10.006

文献信息

• Anticonvulsant Activity of Phenylmethylenehydantoins:  A Structure−Activity Relationship Study
  作者：Jeyanthi Chinnappa Thenmozhiyal、Peter Tsun-Hon Wong、Wai-Keung Chui

  DOI：10.1021/jm030450c

  日期：2004.3.1

  Phenylmethylenehydantoins (PMHs) and their des-phenyl analogues were synthesized and evaluated for anticonvulsant activity using the maximal electroshock seizure (MES) assay. The phenyl rings of PMHs were substituted with a wide spectrum of groups, and the selection of substituents was guided by Craig's plot. Phenylmethylenehydantoins substituted with alkyl (2, 3, 5, 6, 12, 14), halogeno (35, 38, 41), trifluoromethyl (11), and alkoxyl (23) groups at the phenyl ring were found to exhibit good anticonvulsant activity with EDMES(2.5) ranging from 28 to 90 mg/kg. Substitution of polar groups such as -NO2, -CN, and -OH was found to be less active or inactive on PMHs. Replacement of the phenyl ring with heteroaromatic rings reduced or caused the loss of anticonvulsant activity. The study identified two PMHs, 14 (EDMES(2.5) = 28 +/- 2 mg/kg) and 12 (EDMES(2.5) = 39 4 mg/kg), to be the most active candidates of the series, which are comparable to phenytoin (55, EDMES(2.5) = 30 +/- 2 mg/kg) in their protection against seizure. Multivariate analysis performed on the whole series of 54 PMHs further supported the finding that the alkylated phenylmethylenehydantoins are the best acting compounds. The SAR model derived on the basis of 12 of the most active phenylmethylenehydantoins demonstrated good predicting ability (root-mean-square error of prediction (RMSEP) = 0.134; RMSEE = 0.057) and identified LUMO energy and the log P as critical parameters for their anticonvulsant activity.
• US8188130B1
  申请人：——

  公开号：US8188130B1

  公开（公告）日：2012-05-29
• Synthesis of chiral hydantoin derivatives by homogeneous Pd-catalyzed asymmetric hydrogenation
  作者：Bao-De Ma、Sheng-Hua Du、Yu Wang、Xiao-Ming Ou、Ming-Zhi Huang、Li-Xin Wang、Xiao-Guang Wang

  DOI：10.1016/j.tetasy.2016.10.006

  日期：2017.1

  5-Aryl substituted chiral hydantoin derivatives were synthesized via asymmetric hydrogenation of prochiral exocyclic alkenes using a Pd/BINAP catalyst. Moderate to good enantioselectivity were obtained (21-90% ee). A chiral Bronsted acid additive was found to be a key factor to obtain high enantioselectivity. (C) 2016 Elsevier Ltd. All rights reserved.