N-benzyl-2-[(E)-2-phenylethenyl]pyrrolidine | 234092-63-8

• 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: N-benzyl-2-[(E)-2-phenylethenyl]pyrrolidine
• 英文别名: (E)-1-benzyl-2-styrylpyrrolidine；1-benzyl-2-[(E)-2-phenylethenyl]pyrrolidine
• CAS: 234092-63-8
• 化学式: C₁₉H₂₁N
• 分子量: 263.382
• InChiKey: BLCWPLHLOOTWJF-BUHFOSPRSA-N

物化性质

• 沸点：
  379.6±31.0 °C(Predicted)
• 密度：
  1.115±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  N-benzylpent-4-yn-1-amine 在 二氯二茂锆 、 苄基三乙基氯化铵 、 二异丁基氢化铝 、 lithium tert-butoxide 作用下， 以 四氢呋喃 为溶剂， 反应 2.08h， 生成 N-benzyl-2-[(E)-2-phenylethenyl]pyrrolidine
  参考文献：
  名称：

  Carbenylative Amination with N-Tosylhydrazones

  摘要：

  A Pd-catalyzed reaction of vinyl iodides and N-tosylhydrazones that assembles eta(3)-allyl ligands through carbene insertion is demonstrated. Intramolecular trapping with nitrogen nucleophiles generates good yields of cinnamyl and pentadienyl amines like those found in alkaloid natural products. Carbenylative amination was the key reaction to complete the synthesis of the alkaloid caulophyllumine B. Migratory insertion was biased to provide allylamines with optical purity up to 64% ee, but in a lower yield.

  DOI：

  10.1021/ol301385g

文献信息

• Palladium/Benzoic Acid Catalyzed Hydroamination of Alkynes
  作者：Isao Kadota、Akinori Shibuya、Leopold Mpaka Lutete、Yoshinori Yamamoto

  DOI：10.1021/jo990498r

  日期：1999.6.1
• Lutete, Leopold Mpaka; Kadota, Isao; Shibuya, Akinori, Heterocycles, 2002, vol. 58, p. 347 - 357
  作者：Lutete, Leopold Mpaka、Kadota, Isao、Shibuya, Akinori、Yamamoto, Yoshinori

  DOI：——

  日期：——
• Intramolecular Hydroamination of Alkynes Catalyzed by Pd(PPh₃)₄/Triphenylphosphine under Neutral Conditions
  作者：Gan B. Bajracharya、Zhibao Huo、Yoshinori Yamamoto

  DOI：10.1021/jo050412w

  日期：2005.6.1

  The intramolecular hydroamination of alkynes tethered with amino group 1 in the presence of catalytic amounts of Pd(PPh3)(4) and PPh3 in benzene at 100 degrees C proceeded smoothly without the use of any additional acid source to afford five and six-membered nitrogen heterocycles 2 in good to excellent yields. A compulsory addition of carboxylic acid as a cocatalyst was not needed, and the reaction could be carried out under essentially neutral conditions.