3,4-bis(methylene)-N-phenyl-azolidine | 50521-41-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 3,4-bis(methylene)-N-phenyl-azolidine
• 英文别名: 1-phenyl-3,4-dimethylenepyrrolidine；3,4-Dimethylene-1-phenylpyrrolidine；3,4-Dimethylene-N-phenylpyrrolidine；3,4-dimethylene-1-phenyl-pyrrolidine；1-Phenyl-3,4-bis-(methylen)-pyrrolidin；3,4-dimethylidene-1-phenylpyrrolidine
• CAS: 50521-41-0
• 化学式: C₁₂H₁₃N
• 分子量: 171.242
• InChiKey: JGVYDYWKUBQVIL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  丁炔二酸二甲酯 、 3,4-bis(methylene)-N-phenyl-azolidine 以 苯 为溶剂， 生成 dimethyl 8-phenyl-8-azabicyclo<4.3.0>nona-1(6),3-diene-3,4-dicarboxylate
  参考文献：
  名称：

  Preparation and selected reactions of 2,3-bis(bromomethyl)-1,3-butadiene

  摘要：

  DOI：

  10.1021/jo01293a021
• 作为产物：
  描述：

  1,4-二溴-2,3-双(溴甲基)-2-丁烯 在 锌铜偶 作用下， 以 六甲基磷酰三胺 、 乙醚 、 乙腈 为溶剂， 反应 6.5h， 生成 3,4-bis(methylene)-N-phenyl-azolidine
  参考文献：
  名称：

  Preparation and selected reactions of 2,3-bis(bromomethyl)-1,3-butadiene

  摘要：

  DOI：

  10.1021/jo01293a021

文献信息

• Synthesis of Functionalized Pyrrole and Indole Derivatives through Carbometallation of Lithiated Double Bonds
  作者：Francisco J. Fañanás、Alejandro Granados、Roberto Sanz、José M. Ignacio、José Barluenga

  DOI：10.1002/1521-3765(20010702)7:13<2896::aid-chem2896>3.0.co;2-r

  日期：2001.7.2

  derived from bis(2-bromoallyl)amines undergo intramolecular carbometallation of a lithiated double bond, giving dilithiated dihydropyrroles. The cyclizations are promoted by N,N,N',N'-tetramethylethylenediamine (TMEDA). Reaction of these intermediates with electrophiles allows the preparation of some new fused and nonfused five-membered functionalized heterocycles. Although 2-lithioallylamines do

  衍生自双（2-溴烯丙基）胺的双（2-硫代烯丙基）胺经过锂化双键的分子内碳金属化反应，生成二锂化的二氢吡咯。N，N，N′，N′-四甲基乙二胺（TMEDA）促进了环化。这些中间体与亲电试剂的反应允许制备一些新的稠合和非稠合的五元官能化杂环。尽管2-硫代烯丙胺不经历分子间碳金属化，但通过其铜或锆衍生物获得二聚产物。最后，将该新反应应用于2-硫代-N-（2-硫代烯丙基）苯胺产生了3-硫代甲基吲哚衍生物，其通过与亲电试剂反应转化为官能化的吲哚衍生物。
• Synthesis of 1-aryl-3,4-dimethylenepyrrolidines by the thermal elimination of sulfur dioxide
  作者：Raphael M. Ottenbrite、Peter V. Alston

  DOI：10.1002/jhet.5570100518

  日期：1973.10

  was investigated. It was found that the bicyclic compound was obtained in good yields for arylamines with substituent groups with Hammett σ values of less than 0.40. These bicyclic compounds were thermally decomposed to produce the corresponding 1-aryl-3,4-dimethylenepyrrolidines in good yields. Several accompanying products of both of the above reactions were isolated and characterized.

  3,4-双（溴甲基）-2,5-二氢噻吩1,1-二氧化物与芳基胺的反应生成5-芳基-1,3,4,6-四氢噻吩并[3,4- c ]吡咯2,2 -二氧化物进行了研究。已经发现，对于具有取代基的哈米特σ值小于0.40的芳胺，以良好的收率获得了双环化合物。这些双环化合物被热分解，以良好的产率产生相应的1-芳基-3，4-二亚甲基吡咯烷。分离并表征了上述两个反应的几种伴随产物。
• Zirconium-Mediated Intramolecular Coupling of Terminal Alkynes and Their Subsequent Carbonylation: Novel Synthesis of Seven- and Eight-Membered Heterocycles
  作者：José Barluenga、Roberto Sanz、Francisco J. Fañanás

  DOI：10.1002/chem.19970030820

  日期：1997.8

  AbstractThe development of a new method for the intramolecular coupling of terminal alkynes and for the synthesis of seven‐ and eight‐membered benzoheterocycles is reported. The key steps involve the generation of zirconocene‐alkyne complexes from 2‐bromoalkenes and the subsequent intramolecular carbometalation of olefins or acetylides. The 8‐unsubstituted zirconabicyclopentenes were carbonylated to afford unexpected products and allow access to polyfunctionalized molecules from simple starting materials.
• A synthesis of substituted pyrrolidines via a palladium(2+)-catalyzed cyclization. An unusual approach to a carbapenem
  作者：Barry M. Trost、Shyh Fong. Chen

  DOI：10.1021/ja00279a071

  日期：1986.9
• GAONI YE.; SADEH SH., J. ORG. CHEM., 1980, 45, NO 5, 870-881
  作者：GAONI YE.、 SADEH SH.

  DOI：——

  日期：——