N-(2-氯-1-苯基-1-亚乙基)异丙胺 | 131799-53-6

• 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-(2-氯-1-苯基-1-亚乙基)异丙胺
• 英文名称: N-(2-Chloro-1-phenyl-1-ethylidene)isopropylamine
• 英文别名: 2-chloro-1-phenyl-N-propan-2-ylethanimine
• CAS: 131799-53-6
• 化学式: C₁₁H₁₄ClN
• 分子量: 195.692
• InChiKey: MQAXCNKKZRWKMB-UHFFFAOYSA-N

物化性质

• 沸点：
  249.6±32.0 °C(Predicted)
• 密度：
  1.01±0.1 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：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  12.4
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-(2-氯-1-苯基-1-亚乙基)异丙胺 在 四丁基溴化铵 、 水 作用下， 生成 1-苯基-1,4-戊二酮
  参考文献：
  名称：

  NMR Studies of Five-Coordinate Tin Enolate: An Efficient Reagent for Halo Selective Reaction toward .alpha.-Halo Ketone or .alpha.-Halo Imine

  摘要：

  NMR studies of tin enolates 1, in the presence of HMPA, revealed the presence of a five-coordinate O-stannyl enolate 1(h) which contributes to upfield shifts of Sn peaks in the Sn-119 NMR spectrum and increased coupling constants J(Sn-119-C-13), compared with the four-coordinate tin enolate 1(e). The tautomeric equilibrium between C-stannyl ketone 1(k) and O-stannyl enolate 1(e) was changed by the addition of HMPA, the percentage of enol form being increased. The resulting five-coordinate tin enolates 1(h) showed high reactivity and selectivity for halide displacement in reactions with alpha-halo ketones 2. The tin enolates, when coordinated by Bu(4)NBr, effected a selective reaction with alpha-halo imines 5 to give a variety of gamma-imino ketones 6, which were subsequently hydrolyzed to 1,4-diketones or cyclodehydrated to substituted pyrroles 9.

  DOI：

  10.1021/jo00095a011
• 作为产物：
  描述：

  alpha-氯乙酰苯 、 异丙胺 在 四氯化钛 作用下， 以 乙醚 为溶剂， 反应 0.5h， 以84%的产率得到N-(2-氯-1-苯基-1-亚乙基)异丙胺
  参考文献：
  名称：

  α-卤代甲基酮亚胺的合成与反应性

  摘要：

  首次描述了N-（1-卤-2-亚烷基）胺，即α-卤甲基酮亚胺的合成，利用TiCl 4诱导的α-卤甲基酮与伯胺的缩合反应。研究了这些新的α-卤代甲基酮亚胺对亲核试剂（如碘化物，氰化物，醇，醇盐，胺和硫醇盐）的反应性。α-卤甲基酮亚胺是强大的环境亲电体，它经历了各种反应，导致官能化的亚胺和杂环。

  DOI：

  10.1016/s0040-4020(01)88533-1

文献信息

• Synthesis of 2-imino-4-thiazolines, 2-imino-4-alkoxythiazolidines, thiazoles and 4-imidazolin-2-ones from α-halomethyl ketimines
  作者：Norbert De Kimpe、Wim De Cock、Marian Keppens、Dirk De Smaele、Andrea Mészáros

  DOI：10.1002/jhet.5570330429

  日期：1996.7

  nes, 3,4-disubstituted-4-methoxy-2-iminothiazolidines, 2,4-disubstituted-thiazoles, 2-amino-4-substituted-thiazoles and 1,5-disubstituted-4-imidazolin-2-ones, were synthesized from α-chloromethyl and α-bromomethyl ketimines by condensation with potassium thiocyanate, thiourea, ammonium thiocyanate and potassium cyanate.

  各种杂环，包括3,4-二取代-2-亚氨基-4-噻唑啉，3,4-二取代-4-甲氧基-2-亚氨基噻唑烷，2,4-二取代噻唑，2-氨基-4-取代-由α-氯甲基和α-溴甲基酮亚胺与硫氰酸钾，硫脲，硫氰酸铵和氰酸钾缩合，合成噻唑和1,5-二取代-4-咪唑啉-2-酮。
• Highly Coordinated Tin Hydrides: A Novel Synthesis of Tertiary Amines via Hydrostannation of Imines
  作者：Takayo Kawakami、Takayuki Sugimoto、Ikuya Shibata、Akio Baba、Haruo Matsuda、Noboru Sonoda

  DOI：10.1021/jo00114a014

  日期：1995.5

  The highly coordinated tin hydride, Bu(2)SnClH-HMPA (B), is shown to be an effective agent for the reduction of imines. The subsequent alkylation of the resulting intermediate tin amides permitted the preparation of a series of tertiary amines in a one-pot procedure. The spectral identification of the novel tin hydrides, B and Bu(2)SnClH-Bu(4)NF, was accomplished by H-1, C-13, and Sn-119 NMR and FT-IR studies.
• Synthesis and reactivity of α-halomethyl ketimines
  作者：Norbert de Kimpe、Wim de Cock、Christian Stevens

  DOI：10.1016/s0040-4020(01)88533-1

  日期：1992.3

  N-(1-halo-2-alkylidene)amines, i.e. α-halomethyl ketimines, is described for the first time, utilizing the TiCl4-induced condensation of α-halomethyl ketones with primary amines. The reactivity of these new α-halomethylketimines was studied with respect to nucleophiles such as iodide, cyanide, alcohols, alkoxides, amines and thiolates. α-Halomethyl ketimines are powerful ambident electrophiles which underwent

  首次描述了N-（1-卤-2-亚烷基）胺，即α-卤甲基酮亚胺的合成，利用TiCl 4诱导的α-卤甲基酮与伯胺的缩合反应。研究了这些新的α-卤代甲基酮亚胺对亲核试剂（如碘化物，氰化物，醇，醇盐，胺和硫醇盐）的反应性。α-卤甲基酮亚胺是强大的环境亲电体，它经历了各种反应，导致官能化的亚胺和杂环。
• NMR Studies of Five-Coordinate Tin Enolate: An Efficient Reagent for Halo Selective Reaction toward .alpha.-Halo Ketone or .alpha.-Halo Imine
  作者：Makoto Yasuda、Yasuhiro Katoh、Ikuya Shibata、Akio Baba、Haruo Matsuda、Noboru Sonoda

  DOI：10.1021/jo00095a011

  日期：1994.8

  NMR studies of tin enolates 1, in the presence of HMPA, revealed the presence of a five-coordinate O-stannyl enolate 1(h) which contributes to upfield shifts of Sn peaks in the Sn-119 NMR spectrum and increased coupling constants J(Sn-119-C-13), compared with the four-coordinate tin enolate 1(e). The tautomeric equilibrium between C-stannyl ketone 1(k) and O-stannyl enolate 1(e) was changed by the addition of HMPA, the percentage of enol form being increased. The resulting five-coordinate tin enolates 1(h) showed high reactivity and selectivity for halide displacement in reactions with alpha-halo ketones 2. The tin enolates, when coordinated by Bu(4)NBr, effected a selective reaction with alpha-halo imines 5 to give a variety of gamma-imino ketones 6, which were subsequently hydrolyzed to 1,4-diketones or cyclodehydrated to substituted pyrroles 9.