[3,3-Bis-benzyloxymethyl-hex-5-en-(E)-ylidene]-isopropyl-amine | 771581-59-0

• 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: [3,3-Bis-benzyloxymethyl-hex-5-en-(E)-ylidene]-isopropyl-amine
• 英文别名: N-[3,3-Bis[(phenylmethoxy)methyl]-5-hexen-1-ylidene]-2-propanamine；3,3-bis(phenylmethoxymethyl)-N-propan-2-ylhex-5-en-1-imine
• CAS: 771581-59-0
• 化学式: C₂₅H₃₃NO₂
• 分子量: 379.543
• InChiKey: RMUAPVRDYHXMBZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  28
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  30.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [3,3-Bis-benzyloxymethyl-hex-5-en-(E)-ylidene]-isopropyl-amine 在 正丁基锂 、 二氯二茂锆 、 水 、 氯化铵 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 18.0h， 以61%的产率得到((1S,2S)-4,4-Bis-benzyloxymethyl-2-methyl-cyclopentyl)-isopropyl-amine
  参考文献：
  名称：

  Intramolecular Cyclization of Ene-Imine Using Dibutylzirconocene

  摘要：

  The reaction of ene-imine with Cp2ZrBu2 was carried out. When a crude imine, which was prepared from ene-aldehyde and primary amine in the presence of MgSO4, was treated with Cp2ZrBu2 at room temperature overnight, cyclopentane derivative having trans-substituents was obtained in high yield along with a small amount of cyclopentane derivative having cis-substituents. Presumably, cis-zirconacycle is a thermodynamic product. Reactions using various ene-imines were carried out. In the case of ene-imine prepared from ene-aldehyde and (BuNH2)-Bu-t, only cyclopentane having cis-substituents was produced. In this reaction, chiral amine was used, and diastereoselective cyclization of ene-imine was carried out. As a result, cyclopentane derivative having cis-substituents was obtained in an optically active form after hydrogenolysis of the cyclized compound.

  DOI：

  10.1021/jo049662n
• 作为产物：
  描述：

  3,3-bis((benzyloxy)methyl)hex-5-enal 、 异丙胺 在 magnesium sulfate 作用下， 以 苯 为溶剂， 生成 [3,3-Bis-benzyloxymethyl-hex-5-en-(E)-ylidene]-isopropyl-amine
  参考文献：
  名称：

  Intramolecular Cyclization of Ene-Imine Using Dibutylzirconocene

  摘要：

  The reaction of ene-imine with Cp2ZrBu2 was carried out. When a crude imine, which was prepared from ene-aldehyde and primary amine in the presence of MgSO4, was treated with Cp2ZrBu2 at room temperature overnight, cyclopentane derivative having trans-substituents was obtained in high yield along with a small amount of cyclopentane derivative having cis-substituents. Presumably, cis-zirconacycle is a thermodynamic product. Reactions using various ene-imines were carried out. In the case of ene-imine prepared from ene-aldehyde and (BuNH2)-Bu-t, only cyclopentane having cis-substituents was produced. In this reaction, chiral amine was used, and diastereoselective cyclization of ene-imine was carried out. As a result, cyclopentane derivative having cis-substituents was obtained in an optically active form after hydrogenolysis of the cyclized compound.

  DOI：

  10.1021/jo049662n

文献信息

• Intramolecular Cyclization of Ene-Imine Using Dibutylzirconocene
  作者：Muneyoshi Makabe、Yoshihiro Sato、Miwako Mori

  DOI：10.1021/jo049662n

  日期：2004.9.1

  The reaction of ene-imine with Cp2ZrBu2 was carried out. When a crude imine, which was prepared from ene-aldehyde and primary amine in the presence of MgSO4, was treated with Cp2ZrBu2 at room temperature overnight, cyclopentane derivative having trans-substituents was obtained in high yield along with a small amount of cyclopentane derivative having cis-substituents. Presumably, cis-zirconacycle is a thermodynamic product. Reactions using various ene-imines were carried out. In the case of ene-imine prepared from ene-aldehyde and (BuNH2)-Bu-t, only cyclopentane having cis-substituents was produced. In this reaction, chiral amine was used, and diastereoselective cyclization of ene-imine was carried out. As a result, cyclopentane derivative having cis-substituents was obtained in an optically active form after hydrogenolysis of the cyclized compound.