1-methyl-2-benzylidenepyrrolidine | 94532-50-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-methyl-2-benzylidenepyrrolidine
• 英文别名: N-Methyl-5-phenyl-4-pentynylamine；2-benzylidene-1-methyl-pyrrolidine；2-Benzyliden-1-methyl-pyrrolidin；1-Methyl-2-benzyliden-pyrrolidin；(2E)-2-benzylidene-1-methylpyrrolidine
• CAS: 94532-50-0
• 化学式: C₁₂H₁₅N
• 分子量: 173.258
• InChiKey: NYAXXFJEDIEGRD-ZRDIBKRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  1-methyl-2-benzylidenepyrrolidine 在 硫酸 、 溶剂黄146 作用下， 生成 2-苄基-1-甲基吡咯烷
  参考文献：
  名称：

  Lukes, Collection of Czechoslovak Chemical Communications, 1932, vol. 4, p. 351,360

  摘要：

  DOI：
• 作为产物：
  描述：

  N-methyl-5-phenyl-pent-4-ynamide 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以82%的产率得到1-methyl-2-benzylidenepyrrolidine
  参考文献：
  名称：

  New facile synthesis of substituted 2-benzylidene-pyrrolidines by the anionic cyclization of δ-alkynylamines

  摘要：

  DOI：

  10.1016/s0040-4039(00)98070-5

文献信息

• Constrained Geometry Organoactinides as Versatile Catalysts for the Intramolecular Hydroamination/Cyclization of Primary and Secondary Amines Having Diverse Tethered C−C Unsaturation
  作者：Bryan D. Stubbert、Tobin J. Marks

  DOI：10.1021/ja0665444

  日期：2007.4.1

  A series of "constrained geometry" organoactinide complexes, (CGC)An(NMe)(2) (CGC = Me2Si(eta(5)-Me4C5)((BuN)-Bu-t); An = Th, 1; U, 2), has been prepared via efficient in situ, two-step protodeamination routes in good yields and high purity. Both 1 and 2 are quantitatively converted to the neutrally charged, solvent-free dichlorides (1-Cl-2, 2-Cl-2) and slightly more soluble diiodides (1-I-2, 2-I-2) with excess Me3Si-X (X = Cl, I) in non-coordinating solvents. The new complexes were characterized by NMR spectroscopy, elemental analysis, and (for 1 and 2) single-crystal X-ray diffraction, revealing substantially increased metal coordinative unsaturation vs the corresponding Me2SiCp ''(2)AnR(2) (Cp '' = eta(5)-Me4C5; An = Th, R = CH2(SiMe3), 3; An = U, R = CH2Ph, 4) and Cp'(2)AnR(2) (Cp' = eta(5)-Me5C5 ; An = Th, R = CH2(SiMe3), 5; An = U, R = CH2(SiMe3), 6) complexes. Complexes 1-6 exhibit broad applicability for the intramolecular hydroamination of diverse C-C unsaturations, including terminal and internal aminoalkenes (primary and secondary amines), aminoalkynes (primary and secondary amines), aminoallenes, and aminodienes. Large turnover frequencies (N-t up to 3000 h(-1)) and high regioselectivities (>= 95%) are observed throughout, along with moderate to high diastereoselectivities (up to 90% trans ring closures). With several noteworthy exceptions, reactivity trends track relative 5f ionic radii and ancillary ligand coordinative unsaturation. Reactivity patterns and activation parameters are consistent with a reaction pathway proceeding via turnover-limiting CC/CC insertion into the An-N sigma-bond.
• New facile synthesis of substituted 2-benzylidene-pyrrolidines by the anionic cyclization of δ-alkynylamines
  作者：Masao Tokuda、Hirotake Fujita、Hiroshi Suginome

  DOI：10.1016/s0040-4039(00)98070-5

  日期：——
• Cervinka, Otakar; Fabryova, Anna; Jursik, Tomas, Collection of Czechoslovak Chemical Communications, 1988, vol. 53, # 2, p. 308 - 310
  作者：Cervinka, Otakar、Fabryova, Anna、Jursik, Tomas

  DOI：——

  日期：——
• Lukes et al., Collection of Czechoslovak Chemical Communications, 1959, vol. 24, p. 1117,1121
  作者：Lukes et al.

  DOI：——

  日期：——
• TOKUDA, MASAO;FUJITA, HIROTAKE;SUGINOME, HIROSHI, TETRAHEDRON LETT., 31,(1990) N7, C. 5353-5356
  作者：TOKUDA, MASAO、FUJITA, HIROTAKE、SUGINOME, HIROSHI

  DOI：——

  日期：——