2-(4-chlorobenzoylmethylene)-1-methylhexahydropyrimidine | 124927-56-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(4-chlorobenzoylmethylene)-1-methylhexahydropyrimidine
• 英文别名: (2E)-1-(4-chlorophenyl)-2-(1-methyl-1,3-diazinan-2-ylidene)ethanone
• CAS: 124927-56-6
• 化学式: C₁₃H₁₅ClN₂O
• 分子量: 250.728
• InChiKey: VEYHZUCLMJDYDY-UKTHLTGXSA-N

物化性质

• 沸点：
  387.7±42.0 °C(Predicted)
• 密度：
  1.240±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  32.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(4-chlorobenzoylmethylene)-1-methylhexahydropyrimidine 、 1-叠氮基-2,3,5-三苯甲酰氧基-beta-D-呋喃核糖 以 1,2-二氯乙烷 为溶剂， 反应 14.0h， 以50%的产率得到1-(-2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-4-(N-methyl-2-tetrahydropyrimidinyl)-5-(p-chlorophenyl)-1,2,3-triazole
  参考文献：
  名称：

  核糖基化 1,2,3-三唑衍生物的合成

  摘要：

  AbstractRibosylated 1,2,3‐triazole 4 and 5 were synthesized in moderate yields by the reaction of aroyl‐substituted heterocyclic ketene aminals 1 or 2 with 2,3,5‐tri‐O‐benzoyl‐β‐D‐ribofuranosyl azide (3). Their structures were determined by elemental analyses and spectroscopic methods. © 2003 Wiley Periodicals, Inc. Heteroatom Chem 14:487–490, 2003; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.10167

  DOI：

  10.1002/hc.10167
• 作为产物：
  描述：

  1,2-二甲基-1,4,5,6-四氢嘧啶 、 alkaline earth salt of/the/ methylsulfuric acid 在 正丁基锂 作用下， 生成 2-(4-chlorobenzoylmethylene)-1-methylhexahydropyrimidine
  参考文献：
  名称：

  Synthesis and nematocidal activities of new analogs of pyrantel

  摘要：

  A set of new analogs of pyrantel was synthesized in good yields by lithiation of 1,2-dimethyltetrahydropyrimidine with n-butyllithium in tetrahydrofuran and condensation with aromatic esters. Spectrometric studies showed the large influence of intramolecular bonding in the tautomeric equilibria between the possible structures. Anthelmintic screening showed in vitro efficiency against Molinema dessetae, but a weak activity against Rhabditis pseudoelongata and Nippostrongylus brasiliensis.

  DOI：

  10.1016/0223-5234(96)88262-6

文献信息

• Reaction of Heterocyclic Ketene Aminals with α-Bromoketones: A Convenient Synthesis of Pyrrole-Fused 1,3-Diazaheterocycles
  作者：Xiao-Ping Nie、Mei-Xiang Wang、Zhi-Tang Huang

  DOI：10.1055/s-2000-7098

  日期：——

  Heterocyclic ketene aminals reacted with a-bromoketones to give the C-alkylated heterocyclic ketene aminal intermediates which underwent a rapid cyclocondensation reaction to produce pyrrole-fused 1,3-diazaheterocycles.

  杂环乙烯酮缩醛胺与α-溴酮反应得到C-烷基化杂环乙烯酮缩醛胺中间体，该中间体经过快速缩合反应生成吡咯稠合的1,3-二氮杂杂环化合物。
• The aza-ene reaction of heterocyclic ketene aminals with activated carbonyl compounds: a novel and efficient synthesis of γ-lactam-fused diazaheterocycles
  作者：Jian-Heng Zhang、Mei-Xiang Wang、Zhi-Tang Huang

  DOI：10.1039/a808328b

  日期：——

  Reactions of heterocyclic ketene aminals with activated carbonyl compounds are strongly influenced by the structure of the heterocycle moiety. Six-membered heterocyclic ketene aminals with or without an N-methyl group such as 3 and 4 underwent efficient addition and consecutive cyclocondensation reactions with diethyl oxomalonate 9 to produce γ-lactam-fused pyrimidine derivatives 10 and 11 in moderate

  杂环烯酮缩醛与活化的羰基化合物的反应受杂环部分结构的强烈影响。具有或不具有N-甲基（例如3和4）的六元杂环烯酮缩醛胺进行有效加成，并与环氧乙二酸二乙酯9进行连续的环缩合反应，以中等至极好的收率生产γ-内酰胺基融合的嘧啶衍生物10和11。但是，对于五元烯二胺，那些没有任何N-取代基（如6）的化合物缓慢进行相同的反应，根本观察不到与N-甲基和N，N的反应。′-二甲基取代的类似物7和8。杂环烯酮缩醛3也与乙醛酸酯17反应，得到8-芳酰基-7-羟基-6-氧代-1,2,3,4,6,7-六氢吡咯[1 ，2- α ]嘧啶18的收率很好。然而，当使用（1 R，2 S，5 R）-（-）-薄荷基乙醛酸酯17b作为手性底物时，未发现不对称诱导。已经提出了以杂环烯酮缩醛为氮杂烯成分（H–N–CC）的氮杂烯反应机理。还讨论了分子内氢键和杂环尺寸对反应性的影响。
• Huang, Zhi-tang; Liu, Zhi-rong, Synthetic Communications, 1989, vol. 19, # 5and6, p. 943 - 958
  作者：Huang, Zhi-tang、Liu, Zhi-rong

  DOI：——

  日期：——
• Synthesis of O-glycopyranosyl heterocyclic ketene aminals and their use as glycosyl donors
  作者：L Zhan-Jiang

  DOI：10.1016/s0008-6215(96)00221-2

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• Wang, Jian-Chao; Wang, Li-Ben; Huang, Zhi-Tang, Journal of Chemical Research, Miniprint, 1999, # 9, p. 2336 - 2353
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