2-甲基-1,4,5,6-四氢嘧啶 | 4271-95-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 2-甲基-1,4,5,6-四氢嘧啶
• 英文名称: 2-methyl-1,4,5,6-tetrahydropyrimidine
• 英文别名: 2-methyl-1,3-diazacyclohexene；2-methyl-1,4,5,6-tetrahydro-pyrimidine；2-Methyl-1,4,5,6-tetrahydro-pyrimidin；2-methyl-1,4,5,6-tetrahydropyrimidin；2-methyltetrahydropyrimidine；2-Methyl-Δ²-tetrahydropyrimidin
• CAS: 4271-95-8
• 化学式: C₅H₁₀N₂
• 分子量: 98.1478
• InChiKey: ARIDPRZCOYMNQD-UHFFFAOYSA-N

物化性质

• 熔点：
  75 °C
• 沸点：
  91 °C(Press: 4 Torr)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  7
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  24.4
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-甲基-1,4,5,6-四氢嘧啶 在 palladium/alumina 作用下， 生成 2-甲基嘧啶
  参考文献：
  名称：

  The spectroscopic and photophysical effects of the position of methyl substitution. II. 2‐methylpyrimidine

  摘要：

  Laser-induced fluorescence excitation and dispersed fluorescence spectra of the first n–π* transition of jet-cooled 2-methylpyrimidine have been recorded and analyzed. This work extends our earlier study of the spectroscopic and photophysical effects of methyl substitution in 4- and 5-methylpyrimidine. An unusual Fermi resonance involving the 6an0 progression forms the focus of the present study. The 6a10 vibronic transition is observed to be split into a triad of transitions. Dispersed fluorescence spectra are used to identify the dark background state responsible for the Fermi resonance coupling as the 16b1(3a′′2) vibration/internal rotation combination level. This level is selectively coupled by symmetry constraints to 6a1(0a1), leaving the 6a1(1e″) level unperturbed. The positions and intensities of the triad of peaks in the excitation spectrum allow a quantitative determination of the 6a1(0a′1)↔16b1(3a2) coupling matrix element of V=4.1 cm−1. This vibration/internal rotation Fermi resonance is thus typical of the new types of routes to vibrational state mixing which are opened by methyl substitution. Higher members of the 6an0 progression are also involved in Fermi resonance mixing. However, in addition, these levels experience weaker, less state-specific coupling to a bath of same-symmetry states at that energy. The excitation spectrum provides an estimate of the average coupling matrix element of this second tier coupling of ∼1 cm−1.

  DOI：

  10.1063/1.462121
• 作为产物：
  描述：

  2-甲基嘧啶 在 盐酸 、 palladium on activated charcoal 作用下， 生成 2-甲基-1,4,5,6-四氢嘧啶
  参考文献：
  名称：

  PYRIMIDINES. V. DEHALOGENATION AND NUCLEAR REDUCTION OF CERTAIN PYRIMIDINES¹

  摘要：

  DOI：

  10.1021/jo01125a004

文献信息

• Nucleophilic Reactivities and Lewis Basicities of 2-Imidazolines and Related N-Heterocyclic Compounds
  作者：Biplab Maji、Mahiuddin Baidya、Johannes Ammer、Shinjiro Kobayashi、Peter Mayer、Armin R. Ofial、Herbert Mayr

  DOI：10.1002/ejoc.201300213

  日期：2013.6

  predict the rate constants for their reactions with Michael acceptors of known electrophilicity E. A comparison of the nucleophilicity parameters of the imidazoline derivatives 1 with other commonly used nucleophilic organocatalysts shows that they are 10 to 103 times less nucleophilic than PPh3, 1,8-diazabicyclo[5.4.0]undec-7-ene, or 4-(dimethylamino)pyridine. The structure–reactivity relationships of

  由线性自由能方程 log k(20 °C) = sN(N + E) 定义的 2-咪唑啉 1a-d 和相关的 N-杂环化合物 2-5 的亲核参数 N 和 sN 具有通过在 20°C 下通过停流或激光闪光光解技术研究它们与不同取代的二苯甲基离子在二氯甲烷中的反应速率来确定。结果表明，由此获得的 N 和 sN 参数可用于可靠地预测它们与已知亲电性 E 的迈克尔受体反应的速率常数。 咪唑啉衍生物 1 的亲核性参数与其他常用亲核有机催化剂的比较表明，它们的亲核性比 PPh3、1,8-二氮杂双环 [5.4.0] undec-7-ene 或 4-（二甲氨基）吡啶低 10 到 103 倍。
• Reactions of 2-Methyl- and 1,2-Dimethyl-1,4,5,6-tetrahydropyrimidine with Aroyl Chlorides: Diverse Reactivities of Cyclic Ketene N,N′-Acetals Generated in situ
  作者：Charles Pittman Jr.、Guozhong Ye、Sabornie Chatterjee、Aihua Zhou、Bobby Barker、Chunlong Chen、Yingquan Song

  DOI：10.1055/s-0029-1218670

  日期：2010.4

  N′-diaroyl cyclic ketene N,N-acetals that are inert to excess aroyl chlorides. No carbon-carbon bond was formed in these reactions. Conversely, 1,2-dimethyl-1,4,5,6-tetrahydropyrimidine reacted with three equivalents of aroyl chloride under the same conditions to give N-aroyl N′-methyl β,β-dioxo cyclic ketene N,N′-acetals, with formation of two carbon-carbon bonds. Various reactions of cyclic amidines

  2-甲基- 1,4,5,6-四氢用在四氢呋喃-三乙胺芳酰氯两个当量反应，得到Ñ，Ñ '-diaroyl环状烯酮Ñ，Ñ -acetals是惰性的过量芳酰氯。在这些反应中没有形成碳-碳键。相反，在相同条件下，1,2-二甲基-1,4,5,6-四氢嘧啶与三当量的芳酰氯反应，得到N-芳酰基N'-甲基β，β-二氧代环烯酮N，N'-乙缩醛，形成两个碳-碳键。观察到环状am与芳酰氯的各种反应，并就环大小和取代基对就地产生的环状烯酮N，N'-缩醛的反应性的影响进行了讨论。 乙缩醛-芳酰氯-环am-嘧啶
• Process of preparation of heterocyclic compounds employing acetylene ethers
  申请人：ORGANON

  公开号：US02813862A1

  公开（公告）日：1957-11-19

  The invention comprises compounds of the formula <;FORM:0785373/IV (a)/1>; wherein R is a -(CH2)6- or <;FORM:0785373/IV (a)/2>; group and R2 is hydrogen, alkyl, aryl or aralkyl. It comprises also a process for the preparation of compounds of the formula <;FORM:0785373/IV (a)/3>; wherein X is O, S, NH or NR3 (R3 is an alkyl, aryl or aralkyl group), by reacting a compound of the formula R1OC­C-R2, wherein R1 is an alkyl group, with a compound of the formula H2N-R-XH. The reaction is suitably carried out by allowing an alkoxyacetylene, such as an ethoxyacetylene compound, to react with an aminoalcohol, a diamine or a mercaptoamine. Examples describe the preparation according to the above process of (1) 2-methyl-oxazoline; (2) 2 : 4-dimethyl-oxazoline; (3) 2-methylimidazoline; (4) 2-methylbenzimidazole; (5) 2-methylthiazoline; (6) 2-methyl-1-dodecylimidazoline-2; (7) 2-propyl-imidazoline-2; (8) 2-benzylimidazoline-2; (9) 2-methyl- D 2-dihydro-oxazine - 1 : 3; (10) 2 - methyl - 3 : 4 : 5 : 6 - tetrahydropyrimidine; (11) 2-methyl-4 : 5-benzooxazine-1 : 3; (12) 2-methyl-5 : 6-dihydro-1 : 3-thiazine; (13) 2-(1-naphthylmethyl)-2-imidazoline; (14) 2-heptadecyl-2-imidazoline; (15) 2-methyl - 4 : 5 : 6 : 7 - tetrahydro - 1 : 3 - diazepine and (16) 2-methyl-4 : 5 : 6 : 7 : 8 : 9-hexahydro-1 : 3-oxazonine.

  这项发明包括以下公式的化合物：<;FORM:0785373/IV (a)/1>;其中R是一个-(CH2)6-或<;FORM:0785373/IV (a)/2>;基团，R2是氢、烷基、芳基或芳基烷基。它还包括一种制备以下公式的化合物的方法：<;FORM:0785373/IV (a)/3>;其中X是O、S、NH或NR3（R3是烷基、芳基或芳基烷基），通过将公式R1OC­C-R2的化合物（其中R1是烷基）与公式H2N-R-XH的化合物反应。反应通常通过允许烷氧基乙炔，如乙氧基乙炔化合物，与氨醇、二胺或巯胺反应来进行。示例描述了根据上述过程制备的化合物（1）2-甲基噁唑烷；（2）2 : 4-二甲基噁唑烷；（3）2-甲基咪唑烷；（4）2-甲基苯并咪唑；（5）2-甲基噻唑烷；（6）2-甲基-1-十二烷基咪唑-2；（7）2-丙基咪唑-2；（8）2-苄基咪唑-2；（9）2-甲基- D 2-二氢噁啉 - 1 : 3；（10）2-甲基-3 : 4 : 5 : 6-四氢嘧啶；（11）2-甲基-4 : 5-苯噁啉-1 : 3；（12）2-甲基-5 : 6-二氢-1 : 3-噻嗪；（13）2-(1-萘甲基)-2-咪唑烷；（14）2-庚十七烷基-2-咪唑烷；（15）2-甲基-4 : 5 : 6 : 7-四氢-1 : 3-二氮杂环己烷和（16）2-甲基-4 : 5 : 6 : 7 : 8 : 9-六氢-1 : 3-噁唑烷。

• Push–pull alkenes from cyclic ketene-N,N′-acetals: a wide span of double bond lengths and twist angles
  作者：Guozhong Ye、Sabornie Chatterjee、Min Li、Aihua Zhou、Yingquan Song、Bobby Lloyd Barker、Chunlong Chen、Debbie J. Beard、William P. Henry、Charles U. Pittman

  DOI：10.1016/j.tet.2010.02.071

  日期：2010.4

  the reactions of (1) N,N′-dimethyl cyclic ketene-N,N′-acetals with isocyanates, (2) the products from (1) with isocyanates, (3) 2-methylimidazoline and 2-methyl-1,4,5,6-tetrahydropyrimidine with diacid chlorides, (4) 2-methylimidazoline, and 1,2-dimethyl-1,4,5,6-tetrahydropyrimidine with benzoyl chlorides, and (5) 1,2-dimethylimidazoline and 1,2-dimethyl-1,4,5,6-tetrahydropyrimidine with aryl isocyanates

  推挽式烯烃可以通过环烯酮-N，N'-缩醛化学快速获得。从（1）N，N'-二甲基环状烯酮-N，N'-乙缩醛与异氰酸酯的反应中合成了许多具有双键长度和扭曲角跨度的推挽结构，（2）产物从（1）与异氰酸酯，（3）2-甲基咪唑啉和2-甲基-1,4,5,6-四氢嘧啶和二酰氯，（4）2-甲基咪唑啉和1,2-二甲基-1,4,5,6-四氢嘧啶与苯甲酰氯，和（5）1,2-二甲基咪唑啉和1,2-二甲基-1,4,5,6-四氢嘧啶与芳基异氰酸酯。这些反应在非常温和的条件下进行，并且产率中等至优异。八个pxush-pull烯烃的X射线晶体学分析表明，中心双键长度和扭曲对环尺寸（5或6），环结构（稠合或非稠合），电子给体和抽出和推压强度敏感。拉部分分别是电子推或拉基的数目和取代基的空间效应。
• AMIDINE CATALYST FOR CURABLE COMPOSITIONS
  申请人：SIKA TECHNOLOGY AG

  公开号：US20180179165A1

  公开（公告）日：2018-06-28

  The present invention relates to an amidine of the formula (I) and its use as a catalyst for crosslinking a curable composition. The amidine of the formula (I) contains at least one aliphatic amidine group. It is substantially odorless and nonvolatile at room temperature and accelerates the crosslinking of curable compositions very efficiently, without impairing the storage stability of the compositions. It is particularly suitable for compositions based on polymers containing silane groups, with which it is compatible, as a result of which such compositions do not have a tendency to separation or migration or evaporation of the catalyst.

  本发明涉及一种公式（I）的酰胺衍生物及其作为可固化组合物交联催化剂的用途。公式（I）的酰胺衍生物包含至少一个脂肪族酰胺基团。该酰胺衍生物在室温下几乎无味且不挥发，在不损害组合物的储存稳定性的情况下，能够高效地加速可固化组合物的交联反应。它特别适用于基于含有硅烷基的聚合物的组合物，因为它与这些聚合物兼容，从而使得这些组合物不具有催化剂分离、迁移或挥发的倾向。