tert-Butyl-cyclohex-1-enylmethyl-amine | 119353-31-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: tert-Butyl-cyclohex-1-enylmethyl-amine
• 英文别名: N-(cyclohexen-1-ylmethyl)-2-methylpropan-2-amine
• CAS: 119353-31-0
• 化学式: C₁₁H₂₁N
• 分子量: 167.294
• InChiKey: WJEUALFFCRWIQH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  tert-Butyl-cyclohex-1-enylmethyl-amine 在 (R,R)-(-)-N,N’-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediaminocobalt(II) 、 1,3-dicyano-5-fluoro-2,4,6-tris(diphenylamino)benzene 、 N-乙基异丙基胺 、 三乙胺 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 36.0h， 生成 14-(tert-butyl)-14-azadispiro[5.0.57.36]pentadeca-8,11-dien-13-one
  参考文献：
  名称：

  未活化芳烃与未活化烯烃的分子内钴/可见光共催化还原偶联

  摘要：

  借助协同可见光/钴催化系统，开发了未活化芳烃与未活化烯烃的分子内还原偶联方案。这种偶联是通过使用胺作为末端还原剂和水作为主要氢源的自由基级联环化来实现的。在它们的形式中，容易获得的N-烯丙基苯甲酰胺可以以中等至优异的产率转化为相应的螺环己二烯-内酰胺或β-苯乙胺类似物。

  DOI：

  10.1021/acs.orglett.3c03978
• 作为产物：
  描述：

  tert-Butyl-[1-(1-chloro-cyclohexyl)-meth-(E)-ylidene]-amine 在 sodium tetrahydroborate 、 sodium methylate 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 8.0h， 生成 tert-Butyl-cyclohex-1-enylmethyl-amine
  参考文献：
  名称：

  Kimpe, Norbert de; Stanoeva, Elena; Verhe, Roland, Synthesis, 1988, # 8, p. 587 - 592

  摘要：

  DOI：

文献信息

• Additive and Vinylogous Pummerer Reactions of Amido Sulfoxides and Their Use in the Preparation of Nitrogen Containing Heterocycles
  作者：Albert Padwa、Jeffrey T. Kuethe

  DOI：10.1021/jo972093h

  日期：1998.6.1

  The alpha-thiocarbocation generated from the Pummerer re action of N-methyl-N-phenyl-2-[2-(toluene-4-sulfinyl)phenyl]acetamide undergoes Friedel-Crafts reaction at the gamma-carbon with the tethered aromatic ring. Reductive removal of the phenylthio group from the resulting product using Raney nickel occurs in high yield, and the overall reaction represents a new method for the synthesis of a variety of 3-phenyl-substituted oxindoles. Treatment of the related N-benzyl-N-alkyl amido sulfoxide system with trifluoroacetic anhydride affords tetrahydroisoquinolone derivatives. The product distribution encountered coincides with the rotamer population of the starting amide. When the N-benzyl-N-methyl amide is used, only the normal Pummerer product is formed. In this case, the thionium ion is generated in the wrong conformation for pi-cyclization to occur. The corresponding N-tert-butyl amido system, however, exists in a geometric orientation which places the benzylic group in the crucial conformation necessary for pi-cyclization, and consequently, the reaction proceeds smoothly. Related cyclization reactions occur in good yield with the corresponding furanyl and cyclohexenyl N-tert-butyl amido sulfoxides. The additive Pummerer reaction of 3-phenylsulfinyl-N-benzyl-N-tert-butylacrylamide gave products derived from both 5- and 6-exo trig cyclizations. Intramolecular electrophilic aromatic substitution via six-membered ring closure ultimately afforded a dihydropyridone. The competitive process involving ipso attack of the aromatic ring on the thionium ion generates a spiro cyclohexadienyl cation that undergoes fragmentation of the adjacent a-bond. The resulting acyl iminium ion is converted to N-tert-butyl-2-phenyl-3-phenylsulfinylacrylamide upon aqueous workup. Only cyclizations leading to five-membered rings occur with the corresponding indolyl and alkenyl N-tert-butyl amido sulfoxides.
• Kimpe, Norbert de; Stanoeva, Elena; Verhe, Roland, Synthesis, 1988, # 8, p. 587 - 592
  作者：Kimpe, Norbert de、Stanoeva, Elena、Verhe, Roland、Schamp, Niceas

  DOI：——

  日期：——
• Intramolecular Cobalt/Visible Light Cocatalyzed Reductive Coupling of Unactivated Arenes with Unactivated Alkenes
  作者：Jianpeng Cai、Guohui Zeng、Kai Jiang、Hui Luo、Biaolin Yin

  DOI：10.1021/acs.orglett.3c03978

  日期：2024.1.12

  A protocol for the intramolecular reductive coupling of unactivated arenes with unactivated alkenes has been developed with the aid of a cooperative visible light/cobalt catalytic system. This coupling is achieved via radical cascade cyclization using amines as terminal reducing reagents and water as the main hydrogen source. In their form, readily available N-allyl benzamides are converted to the

  借助协同可见光/钴催化系统，开发了未活化芳烃与未活化烯烃的分子内还原偶联方案。这种偶联是通过使用胺作为末端还原剂和水作为主要氢源的自由基级联环化来实现的。在它们的形式中，容易获得的N-烯丙基苯甲酰胺可以以中等至优异的产率转化为相应的螺环己二烯-内酰胺或β-苯乙胺类似物。