2-二甲氧基甲基-丙烯腈 | 7515-08-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-二甲氧基甲基-丙烯腈
• 英文名称: 2-dimethoxymethyl-acrylonitrile
• 英文别名: 2-Dimethoxymethyl-acrylonitril；2-dimethoxy-methylacrylonitrile；2-Dimethoxy-methylacrylonitril；1-Dimethoxymethyl-acrylnitril；2-Dimethoxymethylacrylnitril；2-(Dimethoxymethyl)acrylonitrile；2-(dimethoxymethyl)prop-2-enenitrile
• CAS: 7515-08-4
• 化学式: C₆H₉NO₂
• 分子量: 127.143
• InChiKey: YSWKAZIIPUOFIX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  42.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-二甲氧基甲基-丙烯腈 在 三氯化铝 作用下， 以 甲醇 、 1,2-二氯乙烷 为溶剂， 生成 3,3-dimethoxy-2-[(3,4,5-trimethylphenyl)methyl]propanenitrile
  参考文献：
  名称：

  Tanaka,M. et al., Chemical and pharmaceutical bulletin, 1978, vol. 26, # 5, p. 1558 - 1569

  摘要：

  DOI：
• 作为产物：
  描述：

  甲酸甲酯 、 3-甲氧基丙腈 在 sodium methylate 、 苯 作用下， 生成 2-二甲氧基甲基-丙烯腈
  参考文献：
  名称：

  Monitoring of Partial Pharyngeal Reconstruction

  摘要：

  DOI：

  10.1097/00005537-200203000-00031

文献信息

• 2,4-Diamino-pyrimidine derivatives and processes
  申请人：Hoffman-La Roche Inc.

  公开号：US04033962A1

  公开（公告）日：1977-07-05

  The present invention relates to a new synthesis for the preparation of 5-(substituted benzyl)-2,4-diamino-pyrimidines, including new pyrimidine derivatives. More particularly, a new synthesis of ormetoprin, diaveridine and related compounds, including novel derivatives, is disclosed. The synthesis involves the condensation of a substituted benzene and an acrylonitrile derivative to directly give enol ether intermediates, which upon subsequent reaction by known techniques with guanidine, provides the desired 5-(substituted benzyl)-2,4-diamino-pyrimidines, including novel compounds. The pyrimidine end products are useful as potentiators of sulfonamides and as antibacterial agents.

  本发明涉及一种用于制备5-(取代苄基)-2,4-二氨基嘧啶的新合成方法，包括新的嘧啶衍生物。更具体地，揭示了一种新的制备ormetoprin、diaveridine及相关化合物的合成方法，包括新颖的衍生物。该合成涉及将取代苯和丙烯腈衍生物缩合以直接产生烯醚中间体，随后通过已知技术与胍啶反应，提供所需的5-(取代苄基)-2,4-二氨基嘧啶，包括新颖的化合物。这些嘧啶终产物可用作磺胺类药物的增效剂和抗菌剂。
• The Reaction Mechanism of 2-Dimethoxymethyl-3-methoxypropionitrile with Acetamidine. II. A Novel Reaction Pathway
  作者：Takenori Nishino、Masumi Kiyokawa、Yoshiyuki Miichi、Kanji Tokuyama

  DOI：10.1246/bcsj.45.2010

  日期：1972.7

  The reaction of 2-dimethoxymethyl-3-methoxypropionitrile (1) with acetamidine produces pyrimidopyrimidine (8) via the consecutive process of 1→an intermediate→8. The intermediate was not isolated, but two structures have been proposed for it. We have now succeeded in the isolation of the intermediate and determined it to be 2-methyl-4-amino-5-dimethoxymethyl-5,6-dihydropyrimidine (4). Several key intermediates were also successfully isolated. The novel reaction pathway for the title reaction was concluded to be as follows: the elimination of methanol from 1, followed by the addition of acetamidine affords 3-acetamidinopropionitrile (3), the subsequent quick cyclization of which produces the intermediate, 4; the further elimination of methanol from 4, followed by a replacement reaction with acetamidine, gives an acetamidinomethylene compound (6), which is converted into the final product, 8, via an intermediate (7). Some minor pathways will also be presented.

  2-dimethoxymethyl-3-methoxypropionitrile (1) 与乙脒反应，通过 1→an intermediate→8 的连续过程生成嘧啶嘧啶 (8)。该中间体没有分离出来，但有人提出了它的两种结构。现在我们成功地分离出了中间体，并确定它是 2-甲基-4-氨基-5-二甲氧基甲基-5,6-二氢嘧啶（4）。此外，还成功分离出了几个关键的中间体。上述反应的新反应途径如下：从 1 中消除甲醇，然后加入乙脒，得到 3-乙酰胺基丙腈 (3)，随后快速环化生成中间产物 4；从 4 中进一步消除甲醇，然后与乙脒发生置换反应，得到乙脒亚甲基化合物 (6)，通过中间产物 (7) 转化为最终产物 8。此外还将介绍一些次要途径。
• Cyano-enol ethers
  申请人：Hoffmann-La Roche Inc.

  公开号：US04151196A1

  公开（公告）日：1979-04-24

  The present invention relates to a new synthesis for the preparation of 5-(substituted benzyl)-2,4-diamino-pyrimidines, including new pyrimidine derivatives. More particularly, a new synthesis of ormetoprin, diaveridine and related compounds, including novel derivatives, is disclosed. The synthesis involves the condensation of a substituted benzene and an acrylonitrile derivative to directly give enol ether intermediates, which upon subsequent reaction by known techniques with guanidine, provides the desired 5-(substituted benzyl)-2,4-diamino-pyrimidines, including novel compounds. The pyrimidine end products are useful as potentiators of sulfonamides and as antibacterial agents.

  本发明涉及一种新的合成方法，用于制备5-（取代苯基）-2,4-二氨基嘧啶，包括新的嘧啶衍生物。更具体地，揭示了ormetoprin，diaveridine和相关化合物的新合成方法，包括新颖的衍生物。该合成方法涉及将取代苯和丙烯腈衍生物缩合，直接得到烯醚中间体，随后通过已知技术与胍反应，提供所需的5-（取代苯基）-2,4-二氨基嘧啶，包括新化合物。嘧啶终产品可用作磺胺类药物的增效剂和抗菌剂。
• Process for preparing cyano-enol ethers
  申请人：Hoffmann-La Roche Inc.

  公开号：US04108888A1

  公开（公告）日：1978-08-22

  The present invention relates to a new synthesis for the preparation of 5-(substituted benzyl)-2,4-diamino-pyrimidines, including new pyrimidine derivatives. More particularly, a new synthesis of ormetoprin, diaveridine and related compounds, including novel derivatives, is disclosed. The synthesis involves the condensation of a substituted benzene and an acrylonitrile derivative to directly give enol ether intermediates, which upon subsequent reaction by known techniques with guanidine, provides the desired 5-(substituted benzyl)-2,4-diamino-pyrimidines, including novel compounds. The pyrimidine end products are useful as potentiators of sulfonamides and as antibacterial agents.

  本发明涉及一种新的合成方法，用于制备5-(取代苯基)-2,4-二氨基嘧啶，包括新的嘧啶衍生物。更具体地，本发明揭示了ormetoprin、diaveridine和相关化合物的新合成方法，包括新的衍生物。该合成方法涉及将取代苯和丙烯腈衍生物缩合，直接得到烯醚中间体，随后通过已知技术与胍反应，得到所需的5-(取代苯基)-2,4-二氨基嘧啶，包括新的化合物。嘧啶末端产物可用作磺胺类药物的增效剂和抗菌剂。
• Syntheses of antibacterial 2,4-diamino-5-benzylpyrimidines. Ormetoprim and trimethoprim
  作者：Percy S. Manchand、Perry Rosen、Peter S. Belica、Gloria V. Oliva、Agostino V. Perrotta、Harry S. Wong

  DOI：10.1021/jo00039a006

  日期：1992.6

  A general and mild method for the synthesis of 2,4-diamino-5-benzylpyrimidines was achieved by the Friedel-Crafts reaction between 2-(methoxymethylene)-3-methoxypropanenitrile (10) and an activated aromatic substrate followed by treatment with guanidine. The method is illustrated by a synthesis of ormetoprim (2) in 75% overall yield from 3,4-dimethoxytoluene (12). Efficient syntheses of trimethoprim (1) and 2 were also accomplished via prior base-catalyzed 1,3-prototropic isomerization of cinnamonitriles 19 and 20, respectively, followed by condensation with guanidine. 12 was prepared from 3-bromo-4-methoxytoluene by a Cu(I)-catalyzed displacement of bromine by methoxide and 4,5-dimethoxy-2-methylbenzaldehyde was obtained from 12 in 87% yield by a pyridine-catalyzed Vilsmeier reaction using DMF-POCl3.