1,1-双(二乙氨基)-2-氯乙烯 | 26578-64-3

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 乙烯基卤化物
• 中文名称: 1,1-双(二乙氨基)-2-氯乙烯
• 英文名称: 1,1-bis(diethylamino)-2-chloroethene
• 英文别名: tetra-N-ethyl-chloro-vinylidenediamine；Tetra-N-aethyl-chlor-vinylidendiamin；2-Chlor-1.1-bis-diaethylamino-aethylen；(2-Chloro-1-diethylamino-vinyl)-diethyl-amine；2-chloro-1-N,1-N,1-N',1-N'-tetraethylethene-1,1-diamine
• CAS: 26578-64-3
• 化学式: C₁₀H₂₁ClN₂
• 分子量: 204.743
• InChiKey: NUBOYCACOZZIJL-UHFFFAOYSA-N

物化性质

• 沸点：
  101-102 °C(Press: 13 Torr)
• 密度：
  0.961±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  6.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,1-双(二乙氨基)-2-氯乙烯 生成 四乙基脲
  参考文献：
  名称：

  Ott; Dittus; Weissenburger, Chemische Berichte, 1943, vol. 76, p. 87

  摘要：

  DOI：
• 作为产物：
  描述：

  三氯乙烯 、 二乙胺 在 lithium diethylamide 作用下， 以 乙醚 为溶剂， 生成 1,1-双(二乙氨基)-2-氯乙烯
  参考文献：
  名称：

  Delavarenne,S.Y.; Viehe,H.G., Chemische Berichte, 1970, vol. 103, p. 1209 - 1215

  摘要：

  DOI：

文献信息

• Ambident reactivities of bis(diethylamino)[(methylthio)thiocarbonyl]carbenium salts; reactions at the carbenium carbon atom vs. Thiocarbonyl sulfur atom
  作者：Juzo Nakayama、Takashi Otani、Yoshiaki Sugihara、Akihiko Ishii

  DOI：10.1016/s0040-4039(97)01073-3

  日期：1997.7

  Bis(diethylamino)[(methylthio)thiocarbonyl]carbenium salts (1), a carbenium ion carrying an α-thiocarbonyl group, shown ambident reactivities toward a series of nucleophiles. Thus, they reacted with a typically hard nucleophile, hydroxide, at the carbenium carbon atom, whereas they smoothly reacted with soft nucleophiles, such as carbon, nitrogen, sulfur, and phosphorus nucleophiles, at the thiocarbonyl

  双（二乙氨基）[（甲硫基）硫代羰基]碳鎓盐（1），带有α-硫代羰基的碳正离子，对一系列亲核试剂表现出强烈的反应活性。因此，它们在碳原碳原子上与通常的硬亲核试剂氢氧化物反应，而在硫代羰基硫原子上它们与软亲核试剂，例如碳，氮，硫和磷亲核试剂平稳地反应。
• The reactions of [Pd₂Cl₂(μ-PP)₂] (PP = dppm, dmpm) with Et₂NC≡CNEt₂ in methylene chloride solution: X-ray crystal structures of [Pd₂Cl₂(μ-CH₂)(μ-dppm)₂] and hexakis(diethylamino)benzene, C₆(NEt₂)₆
  作者：Sean R. Klopfenstein、Constanze Kluwe、Kristin Kirschbaum、Julian A. Davies

  DOI：10.1139/v96-260

  日期：1996.11.1

  The binuciear palladium(I) complex, [Pd₂Cl₂(μ-dppm)₂] (dppm = bis(diphenylphosphino)methane), has been shown to react with bis(diethylamino)acetylene, Et₂NC≡CNEt₂, in methylene chloride solution to yield two isolable products, the known methylene-bridged complex, [Pd₂Cl₂(μ-CH₂)(μ-dppm)₂], and hexakis(diethylamino)benzene, C₆(NEt₂)₆, both of which have been characterized crystallographically. The source of the bridging methylene group in [Pd₂Cl₂(μ-CH₂)(μ-dppm)₂] has been shown to be the methylene chloride solvent. A mechanism that accounts for the formation of the two isolable products is proposed. The complex, [Pd₂Cl₂(μdmpm)₂] (dmpm = bis(dimethylphosphino)methane), was similarly found to react with Et₂NC≡NEt₂ in methylene chloride solution to yield [Pd₂Cl₂(μ-CH₂)(μ-dmpm)₂], which was identified spectroscopically. Key words: acetylene, palladium, cyclooligomerization, aminoacetylene, hexakis(diethylamino)benzene.

  双核钯（I）配合物[Pd2Cl2（μ-dppm）2]（dppm = 双（二苯基膦基）甲烷）已被证明可与双（二乙基氨基）乙炔Et2NC≡CNEt2在甲基氯溶液中反应，产生两种可分离的产物：已知的甲基桥联配合物[Pd2Cl2（μ-CH2）（μ-dppm）2]和六（二乙基氨基）苯，C6（NEt2）6，两者均已晶体学表征。[Pd2Cl2（μ-CH2）（μ-dppm）2]中桥联甲基基团的来源被证明是甲基氯溶剂。提出了一种解释形成这两种可分离产物的机理。同样地，[Pd2Cl2（μdmpm）2]（dmpm = 双（二甲基膦基）甲烷）也被发现可在甲基氯溶液中与Et2NC≡NEt2反应，生成[Pd2Cl2（μ-CH2）（μ-dmpm）2]，并经光谱鉴定。关键词：乙炔，钯，环寡聚合，氨基乙炔，六（二乙基氨基）苯。
• Unexpected formation of an inner salt, bis(N,N-diethylamino)carbeniumdithiocarboxylate, from 2-chloro or 2-phenoxy substituted 1,1-bis(N,N-diethylamino)ethylenes and elemental sulfur
  作者：Juzo Nakayama、Isao Akiyama

  DOI：10.1039/c39920001522

  日期：——

  2-Chloro or 2-phenoxy substituted 1,1-bis(N,N-diethylamino)ethylenes 2a and c react with elemental sulfur in benzene at room temperature to give an inner salt, bis(N,N-diethylamino)carbeniumdithiocarboxylate 1a, in excellent yields.

  2-氯或2-苯氧基取代的1,1-双(N,N-二乙氨基)乙烯2a和c在室温下与苯中的元素硫反应，得到内盐，双(N,N-二乙氨基)二硫代羧酸碳鎓1a，产量优异。
• Ott; Dittus, Chemische Berichte, 1943, vol. 76, p. 82
  作者：Ott、Dittus

  DOI：——

  日期：——
• Synthesis and Unique Properties of 4,8-Bis[bis(diethylamino)methylene]-1,2,3,5,6,7-hexaselenacyclooctane
  作者：Juzo Nakayama、Isao Akiyama、Yoshiaki Sugihara、Takehiko Nishio

  DOI：10.1021/ja981901z

  日期：1998.10.1

  Treatment of 1-chloro-2,2-bis(diethylamino)ethene (1) with elemental selenium in refluxing benzene gave 4,8-bis[bis(diethylamino)methylene]-1,2,3,5,6,7-hexaselenacyclooctane (4) in 60% yield. The structure of 4 was determined by X-ray diffraction analysis. Compound 4 behaves as 2,2-bis(diethylamino)-2-ethylium-1-diselenocarboxylate (3) toward a range of reagents. Thus, 4 reacted with Met dimethyl acetylenedicarboxylate, and elemental sulfur, under mild conditions, to give the carbenium iodide 5a, the 1,3-diselenole 6a, and the dithiocarboxylate 2, respectively, in high yields, while the thermolysis in refluxing a-dichlorobenzene afforded the alpha-diselenoamide 7. Evidence for the dissociation of 4 into 3 in solution is provided by IR, UV/vis, and H-1-, C-13-, and Se-77- NMR spectra.