(Z)-5-((E)-3-phenylallylidene)imidazolidine-2,4-dione | 137920-57-1

• 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-((E)-3-phenylallylidene)imidazolidine-2,4-dione
• 英文别名: 5-(cinnamylidene)hydantoin；5-cinnamylidene-imidazolidine-2,4-dione；5-Cinnamyliden-imidazolidin-2,4-dion；(5Z)-5-[(E)-3-phenylprop-2-enylidene]imidazolidine-2,4-dione
• CAS: 137920-57-1
• 化学式: C₁₂H₁₀N₂O₂
• 分子量: 214.224
• InChiKey: CCRLFSLWIUEERQ-DODKFZKMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (Z)-5-((E)-3-phenylallylidene)imidazolidine-2,4-dione 在 氯磺酸 作用下， 反应 72.0h， 以80%的产率得到5-(p-chlorosulfonylcinnamylidene)hydantoin
  参考文献：
  名称：

  Cremlyn, Richard; Jethwa, Sanjay; Joiner, Graham, Phosphorus and Sulfur and the Related Elements, 1988, vol. 36, p. 99 - 110

  摘要：

  DOI：
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 氯乙酸 作用下， 生成 (Z)-5-((E)-3-phenylallylidene)imidazolidine-2,4-dione
  参考文献：
  名称：

  Johnson; Wrenshall, Journal of the American Chemical Society, 1915, vol. 37, p. 2139

  摘要：

  DOI：

文献信息

• Discovery of Novel UV-Filters with Favorable Safety Profiles in the 5-Arylideneimidazolidine-2,4-dione Derivatives Group
  作者：Justyna Popiół、Agnieszka Gunia-Krzyżak、Kamil Piska、Dorota Żelaszczyk、Paulina Koczurkiewicz、Karolina Słoczyńska、Katarzyna Wójcik-Pszczoła、Anna Krupa、Agata Kryczyk-Poprawa、Ewa Żesławska、Wojciech Nitek、Paweł Żmudzki、Henryk Marona、Elżbieta Pękala

  DOI：10.3390/molecules24122321

  日期：——

  Effective protection from the harmful effects of UV radiation may be achieved by using sunscreens containing organic or inorganic UV filters. The number of currently available UV filters is limited and some of the allowed molecules possess limitations such as systemic absorption, endocrine disruption properties, contact and photocontact allergy induction, and low photostability. In the search for new

  通过使用含有有机或无机紫外线过滤剂的防晒霜，可以有效地防止紫外线辐射的有害影响。当前可用的紫外线过滤剂的数量有限，并且一些允许的分子具有局限性，例如全身吸收、内分泌干扰特性、接触和光接触过敏诱导以及低光稳定性。在寻找新的有机紫外线过滤剂的过程中，我们设计并合成了一系列由 5-benzylidene 和 5-(3-phenylprop-2-en-1-ylidene)imidazolidine-2,4-dione (hydantoin) 衍生物组成的系列。测试化合物的光保护活性在甲醇溶液和聚乙二醇制剂中得到证实。最有前途的化合物具有与选定的市售紫外线过滤剂相似的紫外线防护参数值。化合物二乙基2，2'-((Z)-4-((E)-3-(4-甲氧基苯基)allylidene)-2,5-dioxoimidazolidine-1,3-diyl)diacetate (4g) 被表征为一种特别有效的 UVA 光保护剂具有
• Diethyl 2,4-dioxoimidazolidine-5-phosphonates: Horner-Wadsworth-Emmons reagents for the mild and efficient preparation of C-5 unsaturated hydantoin derivatives
  作者：Nicholas A. Meanwell、Herbert R. Roth、Edward C. R. Smith、Donald L. Wedding、J. J. Kim Wright

  DOI：10.1021/jo00024a036

  日期：1991.11

  The phosphonates 19 and 20 were prepared from hydantoin and 1-methylhydantoin, respectively, by way of bromination at C-5 and a subsequent Michaelis-Arbuzov reaction with triethyl phosphite. The Horner-Wadsworth-Emmons-type reagents 19 and 20 were found to react readily with aromatic and aliphatic aldehydes, in the presence of a base, to produce C-5 unsaturated hydantoin derivatives 22 and 26, generally in high yield. The products 22 and 26 were frequently isolated as mixtures of E and Z isomers depending upon the identity of the aldehyde and phosphonate. The isomeric configuration of the products was determined from an analysis of NMR spectral data. Long-range C-13-H-1 coupling constants between the C-4 carbonyl of the hydantoin ring and the olefinic proton were found to be diagnostic of isomer geometry. Conditions were also developed that allowed coupling of 19 and 20 with cyclic and acyclic ketones and alpha-dicarbonyl compounds to afford the corresponding olefinic products. C-5 unsaturated hydantoin derivatives are of synthetic utility as precursors to alpha-amino acid derivatives, pyruvates, and the imidazo[4,5-b]quinolin-2-one heterocyclic ring system, a class of potent inhibitors of low Km cAMP phosphodiesterase and the chromophore present in the siderophore azotobactin.
• JPH06107642A
  申请人：——

  公开号：JPH06107642A

  公开（公告）日：1994-04-19
• US4124760A
  申请人：——

  公开号：US4124760A

  公开（公告）日：1978-11-07