2-(Diacetylmethylene)imidazolidine | 86919-74-6

• 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: 2-(Diacetylmethylene)imidazolidine
• 英文别名: 2-imidazolidinylideneacetylacetone；3-(imidazolidin-2-ylidene)pentane-2,4-dione；3-imidazolidin-2-ylidenepentane-2,4-dione
• CAS: 86919-74-6
• 化学式: C₈H₁₂N₂O₂
• 分子量: 168.195
• InChiKey: ZQZOADFNOZMQIJ-UHFFFAOYSA-N

物化性质

• 熔点：
  164-166 °C
• 沸点：
  358.4±42.0 °C(Predicted)
• 密度：
  1.35 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  -0.43
• 重原子数：
  12.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  58.2
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-(Diacetylmethylene)imidazolidine 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以89%的产率得到1-(imidazolidin-2-ylidene)-propan-2-one
  参考文献：
  名称：

  A Novel Synthesis of Imidazo[2,1-d][1,2,4]triazine and Imidazo[2,1-d][1,2,5]triazepine Derivatives via Ketene-N,N-acetal

  摘要：

  The ketene-S,S-acetal Iwas preparedunder phase-transfer catalysis (PTC) in benzene-carbonate two phase system using tetrabutylammonium bromide as thecatalyst. Upon treatment with 1,2-diaminoethane, followed by hydrolysis with sodium methoxide, I gave 2-(2-oxopropylidene) imidazoline III. Bromination of III and replacement of bromine by hydrazine afforded 2-(1-hydazino-1,2-oxopropylidene)imidazoline V. Compound V was used as a precursor for the preparation of the previously unreported fused nitrogen heterocyclic ring system of imidazotriazine VI, VIII, XI, XII and imidazotriazepine IX, X.

  DOI：

  10.1080/00397919708004107
• 作为产物：
  描述：

  3-[双(甲基磺酰基)亚甲基]-2,4-戊二酮 、 乙二胺 以 乙醇 为溶剂， 以91%的产率得到2-(Diacetylmethylene)imidazolidine
  参考文献：
  名称：

  A Novel Synthesis of Imidazo[2,1-d][1,2,4]triazine and Imidazo[2,1-d][1,2,5]triazepine Derivatives via Ketene-N,N-acetal

  摘要：

  The ketene-S,S-acetal Iwas preparedunder phase-transfer catalysis (PTC) in benzene-carbonate two phase system using tetrabutylammonium bromide as thecatalyst. Upon treatment with 1,2-diaminoethane, followed by hydrolysis with sodium methoxide, I gave 2-(2-oxopropylidene) imidazoline III. Bromination of III and replacement of bromine by hydrazine afforded 2-(1-hydazino-1,2-oxopropylidene)imidazoline V. Compound V was used as a precursor for the preparation of the previously unreported fused nitrogen heterocyclic ring system of imidazotriazine VI, VIII, XI, XII and imidazotriazepine IX, X.

  DOI：

  10.1080/00397919708004107
• 作为试剂：
  描述：

  3-(2-bromophenyl)-3-oxo-N-phenylpropanethioamide 在 copper(l) iodide 、 hydrazine hydrate 、 2-(Diacetylmethylene)imidazolidine 、 sodium hydroxide 作用下， 以 乙醇 、 二甲基亚砜 为溶剂， 反应 3.0h， 生成 ethyl 5-amino-2-(phenylamino)pyrazolo[5,1-a]isoquinoline-6-carboxylate
  参考文献：
  名称：

  铜催化串联反应合成杂环乙酮缩醛为配体的吡唑并[5,1- a ]异喹啉

  摘要：

  CuI催化5-（2-溴芳基）-N-芳基-1 H-吡唑-3-胺与活性乙腈衍生物的串联反应，以良好的产率制备了吡唑并[5,1- a ]异喹啉在温和条件下使用杂环烯酮缩醛（HKA）作为新的配体进行开发。这是HKA首次用作铜催化偶联反应的配体。

  DOI：

  10.1021/jo5020323

文献信息

• Propane-1,3-Dione Derivative or Salt Thereof
  申请人：Hirano Masaaki

  公开号：US20090181964A1

  公开（公告）日：2009-07-16

  It is intended to provide a compound useful as a GnRH receptor antagonist. The inventors further investigated propane-1,3-dione derivatives. As a result, they confirmed that a compound having a benzene ring or a thiophene ring substituted with a group represented by —SO 2 —R 3 in a propane-1,3-dione derivative having 2-(1,3-dihydro-2H-benzimidazol-2-ylidene) has an excellent GnRH receptor antagonistic effect and accomplished the present invention. Because the compound of the present invention has a potent GnRH receptor antagonistic effect, it is useful for the treatment of sex hormone-dependent diseases, particularly GnRH-related diseases. Further, because the compound of the present invention has an excellent metabolic stability in human and few drug interactions, therefore it has preferable characteristics as a pharmaceutical used for the above-mentioned diseases.

  本发明旨在提供一种作为GnRH受体拮抗剂有用的化合物。发明人进一步研究了丙酮酸1,3-二酮衍生物。结果，他们证实，在2-(1,3-二氢-2H-苯并咪唑-2-基亚胺)具有苯环或噻吩环的衍生物中，取代为—SO2—R3基团的化合物具有出色的GnRH受体拮抗作用，并完成了本发明。由于本发明的化合物具有强效的GnRH受体拮抗作用，因此对于治疗性激素依赖性疾病，特别是GnRH相关疾病非常有用。此外，由于本发明的化合物在人体内具有出色的代谢稳定性和较少的药物相互作用，因此作为用于上述疾病的药物具有良好的特性。
• Wang, He-Ting; Wang, Xiao-Jun; Huang, Zhi-Tang, Chemische Berichte, 1990, vol. 123, # 11, p. 2141 - 2145
  作者：Wang, He-Ting、Wang, Xiao-Jun、Huang, Zhi-Tang

  DOI：——

  日期：——
• A FACILE METHOD FOR THE SYNTHESIS OF NOVEL PYRIDINONE DERIVATIVES VIA KETENE<i>N</i>,<i>S</i>-ACETALS
  作者：Eljazi I. Al-Afaleq

  DOI：10.1081/scc-100106218

  日期：2001.1

  A simple and easy method is provided for the synthesis of the novel pyridinone derivatives (3a-e), (8a-c) and (10a-c) by the reaction of ketene acetals (2a-e), (7a-c) and (9a-c) with ethyl cyanoacetate respectively. Compounds (3b-d) reacted with triethyl orthoformate to afford the pyridinone derivatives (4-6) respectively. Compound 7a reacted with ethyl acetoacetate or diethyl malonate to give thiazolopyridinone derivative 11 or 12 respectively.
• WANG, HE-TING;WANG, XIAO-JUN;HUANG, ZHI-TANG, CHEM. BER., 123,(1990) N1, C. 2141-2145
  作者：WANG, HE-TING、WANG, XIAO-JUN、HUANG, ZHI-TANG

  DOI：——

  日期：——
• US7960562B2
  申请人：——

  公开号：US7960562B2

  公开（公告）日：2011-06-14