[3-Chloro-2,2-dimethyl-prop-(E)-ylidene]-isopropyl-amine | 106367-22-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: [3-Chloro-2,2-dimethyl-prop-(E)-ylidene]-isopropyl-amine
• CAS: 106367-22-0
• 化学式: C₈H₁₆ClN
• 分子量: 161.675
• InChiKey: CNFLMHRJNZXMOX-UXBLZVDNSA-N

物化性质

• 沸点：
  208.6±32.0 °C(Predicted)
• 密度：
  0.91±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.73
• 重原子数：
  10.0
• 可旋转键数：
  3.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  12.36
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  [3-Chloro-2,2-dimethyl-prop-(E)-ylidene]-isopropyl-amine 在 次氯酸叔丁酯 、 三乙胺 作用下， 以 丙酮 为溶剂， 反应 79.0h， 生成 4-chloro-2-(N-isopropyl)imino-3,3-dimethylbutanenitrile
  参考文献：
  名称：

  Synthesis of 1-amino-2,2-dialkylcyclopropanecarboxylic acids from β-chloroaldimines

  摘要：

  A variety of hydrogen cyanide adducts of beta-chloroaldimines using acetone cyanohydrin were prepared. The reactive behaviour of these alpha-amino-gamma-chloronitriles towards bases was investigated with the aim to generate 1-aminocyclopropanecarbonitriles, which are precursors for the potentially plant growth regulating 1-aminocyclopropanecarboxylic acids. The synthesis of 1-amino-2,2-dimethylcyclopropanecarboxylic acid (= 2,3-methanovaline) by a reaction sequence involving addition of hydrogen cyanide across beta-chloroaldimines, ring closure to functionalized cyclopropanes and acidic hydrolysis was accomplished. Alternatively the hydrogen cyanide adducts of beta-chloroaldimines were converted into alpha-(N-benzylidene)amino-gamma-chloronitriles, which were ring closed with base and hydrolyzed to afford 1-amino-2,2-dialkylcyclopropanecarbonitriles, the latter serving again as substrates for the hydrolytic conversion into the corresponding 1-amino-2,2-dialkylcyclopropanecarboxylic acids (exemplified for 1-amino-2,2-dimethylcyclopropanecarboxylic acid).

  DOI：

  10.1016/s0040-4020(01)86477-2
• 作为产物：
  描述：

  3-氯-2,2-二甲基-1-丙醇 在 magnesium sulfate 、 pyridinium chlorochromate 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 [3-Chloro-2,2-dimethyl-prop-(E)-ylidene]-isopropyl-amine
  参考文献：
  名称：

  Synthesis of β-Chloroimines

  摘要：

  ß-氯亚胺6是通过与一級胺反应，从ß-氯羰基化合物5制备而成的，主要有两种方法。

  DOI：

  10.1055/s-1986-31508

文献信息

• Synthesis and reactivity of 3-(2-chloroalkyl)-2,2-dihaloaziridines
  作者：Ekaterina Yu. Shinkevich、Kourosch Abbaspour Tehrani、Alexander F. Khlebnikov、Mikhail S. Novikov

  DOI：10.1016/j.tet.2008.05.121

  日期：2008.8

  3-(2-Chloroalkyl)-2,2-dihaloaziridines were synthesized via cycloaddition of dihalocarbenes to the CN double bond of β-chloroimines. Under the action of Lewis acids or HCl, N–C3 bond cleavage occurred, giving rise to N-substituted 2,4-dichloro-3,3-dimethylbutanamides, which were further converted to 3-chloropyrrolidin-2-ones under alkaline conditions. When 2,2-dichloro-3-(2-chloro-1,1-dimethylethy

  通过将二卤卡宾环加成到β-氯亚胺的CN双键上，合成了3-（2-氯烷基）-2,2-二卤代氮丙啶。在路易斯酸或HCl的作用下，发生N–C 3键裂解，产生N-取代的2,4-二氯-3,3-二甲基丁酰胺，在碱性条件下进一步转化为3-氯吡咯烷-2-酮。当2,2-二氯-3-（2-氯-1,1-二甲基乙基）-1-苯基氮丙啶与甲醇钠反应时，氮丙啶开环发生N–C 2键断裂，导致甲基4-氯- 3，3-二甲基-2-（苯基氨基）丁酸酯。
• Rearrangement of 4-(1-Haloalkyl)- and 4-(2-Haloalkyl)-2-azetidinones into Methyl ω-Alkylaminopentenoates via Transient Aziridines and Azetidines
  作者：Yves Dejaegher、Norbert De Kimpe

  DOI：10.1021/jo040161b

  日期：2004.9.1

  The synthesis of 4-(1-haloalkyl)-2-azetidinones and 4-(2-haloalkyl)-2-azetidinones was investigated with use of the Staudinger reaction between in situ generated ketenes and alpha-haloimines or beta-haloimines. This new class of functionalized 2-azetidinones was further evaluated for its potential use as intermediates in the synthesis of highly functionalized compounds. The reaction of 4-(1-haloalkyl)-2-azetidinones and 4-(2-haloalkyl)-2-azetidinones with sodium methoxide in methanol yielded ring-opened products, i.e., methyl 2-alkoxy-4-(alkylamino)pentenoate and methyl 5-(alkylamino)pentenoate, respectively. Further attention was paid in detail to the reaction mechanism involved in this peculiar transformation. It was proven that these reactions proceeded via intermediate aziridines or azetidines.
• SULMON, P.;DE, KIMPE, N.;VERHE, R.;DE, BUYCK, L.;SCHAMP, N., SYNTHESIS, BRD, 1986, N 3, 192-195
  作者：SULMON, P.、DE, KIMPE, N.、VERHE, R.、DE, BUYCK, L.、SCHAMP, N.

  DOI：——

  日期：——