1-苄基-3-氯-4-(氯甲基)吡咯烷-2-酮 | 61213-19-2

• 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: 1-苄基-3-氯-4-(氯甲基)吡咯烷-2-酮
• 英文名称: N-benzyl-3-chloro-4-chloromethyl-pyrrolidin-2-one
• 英文别名: N-benzyl-3-chloro-4-chloromethyl-2-pyrrolidinone；N-Benzyl-3-chlor-4-chlormethyl-2-pyrrolidinon；2-Pyrrolidinone, 3-chloro-4-(chloromethyl)-1-(phenylmethyl)-；1-benzyl-3-chloro-4-(chloromethyl)pyrrolidin-2-one
• CAS: 61213-19-2
• 化学式: C₁₂H₁₃Cl₂NO
• 分子量: 258.147
• InChiKey: FEOZBZXSEJHJJL-UHFFFAOYSA-N

物化性质

• 沸点：
  434.3±40.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-苄基-3-氯-4-(氯甲基)吡咯烷-2-酮 在 四氢呋喃 、 magnesium 作用下， 以 甲苯 为溶剂， 生成 3-苄基-3-氮杂双环[3.1.0]-2-己酮
  参考文献：
  名称：

  Olefin Cyclopropanations via Sequential Atom Transfer Radical Addition-Dechlorination Reactions

  摘要：

  在有机合成中，环丙烷化反应通常使用Simmons-Smith类型试剂进行，或者通过过渡金属催化的烯烃与重氮化合物的反应进行。描述了一种基于两步反应序列的合成取代环丙烷的新方法。烯烃通过Ru催化的原子转移自由基加成（ATRA）过程与1,1'-二氯化物反应，生成的1,3-二氯化物通过与镁的还原偶联直接转化为环丙烷。这种一锅法适用于各种底物，并可以以分子间或分子内的方式进行。

  DOI：

  10.2533/chimia.2010.188
• 作为产物：
  描述：

  N-烯丙基苄胺 在 2,2'-联吡啶 、 copper(l) chloride 三乙胺 作用下， 以 乙醚 、 1,2-二氯乙烷 为溶剂， 反应 4.0h， 生成 1-苄基-3-氯-4-(氯甲基)吡咯烷-2-酮
  参考文献：
  名称：

  Transition metal-catalyzed radical cyclizations: a low-temperature process for the cyclization of N-protected N-allyltrichloroacetamides to trichlorinated .gamma.-lactams and application to the stereoselective preparation of .beta.,.gamma.-disubstituted .gamma.-lactams

  摘要：

  Cyclizations of N-substituted N-allyltrichloroacetamides, where the substituent is an alkyl, Cbz, Boc, Ts, or Ms group, are catalyzed by a 1:1 mixture of CuCl and bipyridine to give the corresponding beta,gamma-trichlorinated gamma-lactams in high yields. The reactions proceed at temperatures from -78-degrees-C to room temperature. Cyclizations of N-allyltrichloroacetamides of acyclic secondary allylic amines are achieved with good selectivity; the cis/trans ratios of the gamma-lactams formed were dependent on the substituents on the nitrogen atom. The stereochemical outcome is compared with that of free-radical cyclization.

  DOI：

  10.1021/jo00054a034

文献信息

• Functional rearrangement of polychlorinated pyrrolidin-2-ones to 5-imino-lactams promoted by n-propylamine
  作者：Chiara Danieli、Franco Ghelfi、Adele Mucci、Ugo M. Pagnoni、Andrew F. Parsons、Mariella Pattarozzi、Luisa Schenetti

  DOI：10.1016/j.tet.2004.09.073

  日期：2004.12

  The reaction of 4-methyl-pyrrolidin-2-ones, chlorinated at the C(3) and C(6) positions, with n-propylamine constitutes a new method for the preparation of 5-propylimino-pyrrolidin-2-ones or 3-pyrrolin-2-ones in generally good yields. The transformation involves a series of eliminations, substitutions and double bond shifts. This constitutes a remarkable example of a functional rearrangement.

  在C（3）和C（6）位置氯化的4-甲基-吡咯烷-2-酮与正丙胺的反应构成了制备5-丙基亚氨基-吡咯烷-2-酮或3的新方法-吡咯啉-2-酮通常具有良好的收率。转化涉及一系列消除，取代和双键移位。这构成了功能重新布置的显着示例。
• Easy approach to 3-benzylimino-2-pyrrolidinones from 3-chloro-4-chloromethyl-2-pyrrolidinones
  作者：Franco Ghelfi、Gianluca Ghirardini、Emanuela Libertini、Luca Forti、Ugo M. Pagnoni

  DOI：10.1016/s0040-4039(99)01798-0

  日期：1999.12

  3-chloro-4-chloromethyl-2-pyrrolidinones, benzylamine and NaI in THF at 80°C. An endo-dehydrohalogenation followed by a SN2′ substitution on the intermediate allyl chloride, and finally a shift of the exo-double bond to Δ3 with attendant tautomerization, appears to be the most probable reaction mechanism.

  通过在80℃下将3-氯-4-氯甲基-2-吡咯烷酮，苄胺和NaI在THF中加热，可以高收率制备3-苄基氨基-2-吡咯烷酮。一内切-dehydrohalogenation后跟一个SN 2 '在中间烯丙基氯取代，最后的移位外型-双键来Δ 3与伴随的互变异构化，似乎是最有可能的反应机理。
• Copper-catalyzed facile carbon-carbon bond forming reactions at the α-position of α,α,γ-trichlorinated γ-lactams
  作者：Sho-ichi Iwamatsu、Hideo Kondo、Kouki Matsubara、Hideo Nagashima

  DOI：10.1016/s0040-4020(98)01198-3

  日期：1999.2

  resulted in facile activation of their carbon-chlorine bond at the α-position. Addition of the carbon moiety and the chlorine atom to olefins furnished the carbon-carbon bond forming reaction at the α-position of the carbonyl group. In certain trichlorinated γ-lactams including a carbon-carbon double bond at an appropriate position, intramolecular addition reactions took place to give bicyclic lactams

  用催化量的CuCl（联吡啶）配合物处理α，α，γ-三氯化γ-内酰胺会导致其在α-位的碳-氯键易于活化。碳部分和氯原子加到烯烃上，在羰基的α-位提供了碳-碳键形成反应。在某些在适当位置包括碳-碳双键的三氯化γ-内酰胺中，发生分子内加成反应以得到双环内酰胺。由N环化组成的顺序反应还实现了-烯丙基三氯乙酰胺，然后在内酰胺的α位上形成分子间或分子内碳-碳键。催化剂的效率和反应速率取决于γ-内酰胺的氮原子的保护基团。N-甲苯磺酰基衍生物比相应的N-苄基同源物给出更好的结果。代表性产物的分子结构揭示了反应的立体化学结果。
• Acyclic and alicyclic N-substituted halo-2-pyrrolidinones and their
  申请人：Stauffer Chemical Company

  公开号：US04069038A1

  公开（公告）日：1978-01-17

  Acyclic and alicyclic N-substituted halo-2-pyrrolidinones having the formula ##STR1## in which Q is oxygen or sulfur; R is lower alkyl, haloalkyl, alkenyl, cycloalkyl, cycloalkylalkyl, benzyl and chlorobenzyl; X is hydrogen or chlorine, Y is chlorine or bromine and Z is chlorine or bromine, provided that when R is allyl, Y and Z are each chlorine or bromine, and provided that when R is cyclohexyl, X is other than chlorine. The compounds of this invention are prepared by a novel process and are useful as herbicides.

  本发明涉及一种公式为##STR1##的无环和脂环N取代卤代-2-吡咯烷酮，其中Q为氧或硫；R为低碳基，卤代碳基，烯基，环烷基，环烷基碳基，苄基和氯苄基；X为氢或氯，Y为氯或溴，Z为氯或溴，但当R为烯丙基时，Y和Z均为氯或溴，当R为环己基时，X不是氯。本发明的化合物通过一种新颖的方法制备，可用作除草剂。
• Preparation of acyclic and alicyclic N-substituted halo-2-pyrrolidinones
  申请人：Stauffer Chemical Company

  公开号：US04119636A1

  公开（公告）日：1978-10-10

  Acyclic and alicyclic N-substituted halo-2-pyrrolidinones having the formula ##STR1## in which Q is oxygen or sulfur; R is lower alkyl, haloalkyl, alkenyl, cycloalkyl, cycloalkylalkyl, benzyl and chlorobenzyl; X is hydrogen or chlorine, Y is chlorine or bromine and Z is chlorine or bromine, provided that when R is allyl, Y and Z are each chlorine or bromine, and provided that when R is cyclohexyl, X is other than chlorine. The compounds of this invention are prepared by a novel process and are useful as herbicides.

  本发明涉及一种具有以下式子的非环状和环状N-取代卤代-2-吡咯烷酮：##STR1## 其中Q是氧或硫；R是低碳基、卤代碳基、烯基、环烷基、环烷基烷基、苯甲基和氯苯甲基；X是氢或氯，Y是氯或溴，Z是氯或溴，但当R是烯丙基时，Y和Z各自是氯或溴，且当R是环己基时，X不是氯。本发明的化合物通过一种新颖的方法制备，可用作除草剂。