2-(benzoylmethylene)-1-methylhexahydropyrimidine | 124927-52-2

• 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-(benzoylmethylene)-1-methylhexahydropyrimidine
• 英文别名: (2E)-2-(1-methyl-1,3-diazinan-2-ylidene)-1-phenylethanone
• CAS: 124927-52-2
• 化学式: C₁₃H₁₆N₂O
• 分子量: 216.283
• InChiKey: YLNATKYRDQWIOV-JLHYYAGUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 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-(benzoylmethylene)-1-methylhexahydropyrimidine 、 溴丙酮 在 4 A molecular sieve 作用下， 以 1,4-二氧六环 为溶剂， 反应 5.0h， 以66%的产率得到(1,6-dimethyl-3,4-dihydro-2H-pyrrolo[1,2-a]pyrimidin-8-yl)-phenylmethanone
  参考文献：
  名称：

  杂环烯酮胺与 α-溴酮的反应：吡咯稠合 1,3-二氮杂杂环的便捷合成

  摘要：

  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。

  DOI：

  10.1055/s-2000-7098
• 作为产物：
  描述：

  3,3-双甲基磺酰基-1-苯丙酮 、 3-甲氨基丙胺 以 乙醇 为溶剂， 反应 12.0h， 以97%的产率得到2-(benzoylmethylene)-1-methylhexahydropyrimidine
  参考文献：
  名称：

  Huang, Zhi-tang; Liu, Zhi-rong, Synthetic Communications, 1989, vol. 19, # 5and6, p. 943 - 958

  摘要：

  DOI：

文献信息

• 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。
• Acylation of Heterocyclic Ketene Aminals with Propionyl Chloride
  作者：Zhi-Tang Huang、Jian-Chao Wang、Li-Ben Wang

  DOI：10.1080/00397919608004539

  日期：1996.6

  Abstract Heterocyclic ketene aminals 1 or 2 reacted with propionyl chloride to give both the mono-N-and C-acylated products 4 and 5 or 6 and 7. While N-methyl heterocyclic ketene aminals 3 reacted with propionyl chloride under the same condition, the reaction took place in complexity. Besides N-and C-acylation, the O-attack and heterocyclic ring cleavage also occurred to give products 8 and 9.

  摘要 杂环烯酮缩醛胺 1 或 2 与丙酰氯反应，得到单 N-和 C-酰化产物 4 和 5 或 6 和 7。而 N-甲基杂环烯酮缩胺醛缩胺 3 在相同条件下与丙酰氯反应，反应在复杂中发生。除了 N-和 C-酰化外，O-攻击和杂环裂解也产生了产物 8 和 9。
• Synthesis of ribosylated 1,2,3-triazole derivatives
  作者：Zhong-Xu Ren、Xiao-Min Chen、Zhan-Jiang Li、Zhi-Tang Huang

  DOI：10.1002/hc.10167

  日期：——

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

  DOI：——

  日期：——
• Stereoselective synthesis of O-galactosides of benzoyl-substituted heterocyclic ketene aminals
  作者：Zhong-Xu Ren、Li-Ben Wang、Zhan-Jiang Li、Zhi-Tang Huang

  DOI：10.1016/s0008-6215(98)00131-1

  日期：1998.7

  The stereoselective synthesis of O-galactosides of benzoyl-substituted heterocyclic ketene aminals was investigated. The benzoyl-substituted heterocyclic ketene aminals 1-4 reacted with 2,3,4,6-tetra-O-acetyl-alpha-D-galactopyranosyl bromide (5) in the presence of calcium hydride to give O-galactosides of benzoyl-substituted heterocyclic ketene aminals 6-9 with the Z-configuration. In comparison, 1-2 reacted with 5 in the presence of mercuric cyanide to give O-galactosides of benzoyl-substituted heterocyclic ketene aminals 10-11 with the E-configuration. Satisfactory results have been obtained in terms of both stereoselectivity and yield, and the beta-anomers are the sole products. (C) 1998 Elsevier Science Ltd. All rights reserved.