3-chloro-N-phenyl-α-2-propenylbenzenemethanamine

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 3-chloro-N-phenyl-α-2-propenylbenzenemethanamine
• 英文别名: N-[1-(3-chlorophenyl)but-3-enyl]aniline
• 化学式: C₁₆H₁₆ClN
• 分子量: 257.763
• InChiKey: GHIYPSQTWXNUHZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  N-(3-chlorobenzylidene)aniline 、 3-溴丙烯 在 indium 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以93%的产率得到3-chloro-N-phenyl-α-2-propenylbenzenemethanamine
  参考文献：
  名称：

  Asymmetric Allylation of Aldimines with Indium and (+)‐Cinchonine

  摘要：

  By applying indium and allyl bromide, aldimines were converted into homoallyl amines with excellent yields. The addition of (+)-cinchonine to the reaction mixture yielded enantioselective allylation with 22-44% ee.

  DOI：

  10.1081/scc-200061721

文献信息

• A distinct approach for the rapid synthesis of homoallylic amines starting directly from nitro compounds in water
  作者：Biswanath Das、Gandham Satyalakshmi、Kanaparthy Suneel、Boddu Shashikanth

  DOI：10.1016/j.tetlet.2008.10.010

  日期：2008.12

  Three-component reactions of nitroarenes, benzaldehydes, and allyltributylstannane using indium in dilute aqueous HCl at room temperature afford the corresponding homoallylic amines in high yields within 5-10 min. The conversion in one-pot synthesis involves the following steps: (i) reduction of nitro compounds to amines, (ii) formation of imines from amines and aldehydes, and (iii) allylation of imines. (C) 2008 Elsevier Ltd. All rights reserved.
• SmI₂MEDIATED ALLYLATION OF ALDIMINES WITH ALLYL BROMIDE
  作者：Byeong Hyo Kim、Rongbi Han、Ryun Ju Park、Kyung Ho Bai、Young Moo Jun、Woonphil Baik

  DOI：10.1081/scc-100104829

  日期：2001.1

  In a mild reaction with SmI2, aldimines have been converted into homoallyl amines in good yields.
• Asymmetric Allylation of Aldimines with Indium and (+)‐Cinchonine
  作者：Rongbi Han、Seung Hyuk Choi、Kee In Son、Young Moo Jun、Byung Min Lee、Byeong Hyo Kim

  DOI：10.1081/scc-200061721

  日期：2005.6.1

  By applying indium and allyl bromide, aldimines were converted into homoallyl amines with excellent yields. The addition of (+)-cinchonine to the reaction mixture yielded enantioselective allylation with 22-44% ee.