N,N-二甲基-N'-(4-溴苯基)甲脒 | 13181-50-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N,N-二甲基-N'-(4-溴苯基)甲脒
• 英文名称: N²-p-bromophenyl-N¹,N¹-dimethylformamidine
• 英文别名: N'-(4-bromophenyl)-N,N-dimethylformimidamide；N,N-dimethyl-N'-p-bromophenylformamidine；N2-(4-bromo-phenyl)-N1,N1-dimethyl-formamidine；N-p-Bromphenyl-N',N'-dimethylformamidin；N'-(p-Bromophenyl)-N,N-dimethylformamidine；N'-(4-bromophenyl)-N,N-dimethylmethanimidamide
• CAS: 13181-50-5
• 化学式: C₉H₁₁BrN₂
• 分子量: 227.104
• InChiKey: OJKJZQJONGTMRZ-UHFFFAOYSA-N

物化性质

• 保留指数：
  1732;1732

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  15.6
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2925290090

反应信息

• 作为反应物：
  描述：

  N,N-二甲基-N'-(4-溴苯基)甲脒 在 sodium tetrahydroborate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 4-溴-N-甲基苯胺
  参考文献：
  名称：

  Reductive Monoalkylation of Aromatic Amines via Amidine Intermediates

  摘要：

  使用脒类作为中间体进行芳香胺的还原单烷基化反应的便利性与高效性已被证明。这种单烷基化反应既可以分两步合成，也可以采用一步法操作。本文展示的几个实例清楚地表明了这种新方法在芳香胺的甲基化或乙基化反应中的实用性，包括未保护的核苷。

  DOI：

  10.1055/s-2001-13378
• 作为产物：
  描述：

  在 sodium carbonate 作用下， 以 水 为溶剂， 生成 N,N-二甲基-N'-(4-溴苯基)甲脒
  参考文献：
  名称：

  A Base Promoted Synthesis of N,N-dimethylformamidines

  摘要：

  DOI：

  10.5012/bkcs.2013.34.5.1537

文献信息

• Cycloaddition von Heterocumulenen an C?N-Bindungssysteme. 1. Mitteilung. Perhydro-s-triazindione und Perhydro-s-triazinyl-harnstoffe aus N,N,N?-trisubstituieten Formamidinen und Isocyanaten
  作者：Karl Seckinger

  DOI：10.1002/hlca.19730560221

  日期：1973.1.31

  The addition of methyl isocyanate to N,N-dimethyl-N′-arylformamidines 4d–4r leads to the perhydro-s-triazine-diones 5d–5o and to the s-triazinylureas 10a–10k. The mechanism of formation is discussed.

  加入甲基异氰酸酯与N，N-二甲基-N'- arylformamidines图4d - 4R通向全氢小号嗪二酮图5d - 50和到小号-triazinylureas 10A - 10K。讨论了形成机理。
• N,N-Diisopropylformamidine (DIFA) Protection of Anilines in Metalation Reactions
  作者：Paul Zhichkin、Sergiy Krasutsky、Ravi Krishnamoorthy

  DOI：10.1055/s-0030-1259058

  日期：2010.12

  A novel N,N-diisopropylformamidine (DIFA) protecting group for anilines was studied. Metalation is often metal-directed by this weakly coordinating and bulky group, making it complementary to ortho-metalation directed by tert-butylcarbamate and pivaloylamide groups and to regular electrophilic reactions of anilines. Importantly, DIFA is removed under nucleophilic conditions and is stable toward acids, thus being orthogonal to tert-butylcarbamate, N-tert-butylamide, and other acid-labile protecting groups.

  研究了一种新型N,N-二异丙基甲酰胺保护基（DIFA）用于对苯胺。金属化过程常常受到这种弱配位且体积庞大的基团的金属导向，使其与由叔丁基碳酸酯和伐尔酰胺基团引导的邻位金属化相辅相成，并且与对苯胺的常规电亲反应兼容。重要的是，DIFA在亲核条件下可被去除，并且对酸稳定，因此与叔丁基碳酸酯、N-叔丁酰胺和其他酸敏感的保护基具有正交性。
• A versatile new synthesis of quinolines and related fused pyridines, Part 5. The synthesis of 2-chloroquinoline-3-carbaldehydes
  作者：Otto Meth-Cohn、Bramha Narine、Brian Tarnowski

  DOI：10.1039/p19810001520

  日期：——

  Acetanilides are converted into 2-chloroquinoline-3-carbaldehydes in good yield by the action of Vilsmeier's reagent in phosphoryl chloride solution. The reaction is shown to involve successive conversion of the acetanilide in to an imidoyl chloride and then an N-(α-chlorovinyl)aniline. The latter enamine is diformylated at its β-position and subsequently cyclised to the chloroquinolinecarbaldehyde

  在Vylsmeier试剂在磷酰氯溶液中的作用下，乙酰苯胺以高收率转化为2-氯喹啉-3-甲醛。已表明该反应涉及将乙酰苯胺依次转化为亚氨酰氯，然后转化为N-（α-氯乙烯基）苯胺。后者的烯胺在其β-位被二甲酰化，随后环化成氯喹啉甲醛。可以在几种情况下分离二甲酰化的中间体，并分别用多磷酸环化。
• Oszczapowicz, Janusz; Raczynska, Ewa, Polish Journal of Chemistry, 1983, vol. 57, # 4/5/6, p. 419 - 428
  作者：Oszczapowicz, Janusz、Raczynska, Ewa

  DOI：——

  日期：——
• Amidines. Part 31. pK_avalues of N¹,N¹-dialkyl-N²-phenylformamidines in water–ethanol solutions
  作者：Janusz Oszczapowicz、Jolanta Jaroszewska-Manaj

  DOI：10.1039/p29910001677

  日期：——

  The pK(a) values of three series (30 compounds in all) of N1,N1-dialkyl-N2-phenylformamidines (XC6H4N = CH-NRR) have been measured in water-ethanol mixtures. The obtained pK(a) values of the amidines have been correlated with Hammett-type substituent constants and the pK(a) values of the corresponding primary amines determined in the same solvent. The applicability of various sigma-values is discussed and it is shown that, in each case, for substituents on the phenyl ring at the amino nitrogen atom sigma-degrees values should be used. It is found that the slopes of regression lines for correlations with Hammett-type constants depend on the substituents at the amino nitrogen atom, as well as on the solvent.