N-(2-bromoprop-2-en-1-yl)cyclopentanamine | 1179978-05-2

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 乙烯基卤化物
• 英文名称: N-(2-bromoprop-2-en-1-yl)cyclopentanamine
• 英文别名: N-(2-bromoprop-2-enyl)cyclopentanamine
• CAS: 1179978-05-2
• 化学式: C₈H₁₄BrN
• 分子量: 204.11
• InChiKey: KZLUWTZDMKELIR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 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：

  N-(2-bromoprop-2-en-1-yl)cyclopentanamine 在 氨 、 sodium amide 作用下， 以 乙醚 为溶剂， 反应 3.0h， 以17%的产率得到1-cyclopentyl-2-methyleneaziridine
  参考文献：
  名称：

  Sodium Amide Induced Cyclization of 2-Iodoprop-2-enylamines: Application to the Synthesis of 1-Aryl-2-methyleneaziridines

  摘要：

  The effect of the halogen on the rate of sodium amide induced cyclization of 2-haloprop-2-enylamines to methyleneaziridines is studied. Using DFT calculations and competition experiments, it is shown to proceed faster using iodide-based substrates. A practical route to 1-aryl-2-methyleneaziridines is devised based on these observations and their further rearrangement to cyclopropanimines explored.

  DOI：

  10.1055/s-0034-1380521
• 作为产物：
  描述：

  环戊胺 、 2,3-二溴-1-丙烯 在 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以61%的产率得到N-(2-bromoprop-2-en-1-yl)cyclopentanamine
  参考文献：
  名称：

  Sodium Amide Induced Cyclization of 2-Iodoprop-2-enylamines: Application to the Synthesis of 1-Aryl-2-methyleneaziridines

  摘要：

  The effect of the halogen on the rate of sodium amide induced cyclization of 2-haloprop-2-enylamines to methyleneaziridines is studied. Using DFT calculations and competition experiments, it is shown to proceed faster using iodide-based substrates. A practical route to 1-aryl-2-methyleneaziridines is devised based on these observations and their further rearrangement to cyclopropanimines explored.

  DOI：

  10.1055/s-0034-1380521

文献信息

• Copper-catalyzed cascade reactions of N-(2-bromoallyl)amines with KHCO3 as the C1 source: an efficient process for the synthesis of oxazolidin-2-ones
  作者：Hongwei Jin、Yukun Yang、Jianhong Jia、Binjie Yue、Bo Lang、Jianquan Weng

  DOI：10.1039/c4ra02304h

  日期：——

  A novel synthesis of oxazolidin-2-ones by carbamic acid formation and a subsequent copper-catalyzed intramolecular vinylation from N-(2-bromoallyl)amines and KHCO3 was developed. KHCO3 was used as a C1 source and base in this efficient and convenient cascade process.

  通过氨基甲酸的形成和随后的铜催化的N-（2-溴烯丙基）胺和KHCO 3的分子内乙烯基化反应，新合成了恶唑烷-2-酮。在这种高效，便捷的级联过程中，KHCO 3被用作C1的来源和碱。
• Switchable Copper-Catalyzed Cascade Synthesis of Thiazolidine-2-thiones and Thiazole-2(3H)-thiones
  作者：Hong-Wei Jin、Jian-Quan Weng、Bin-Jie Yue、Meng Xu、Yu-Kun Yang

  DOI：10.1055/s-0034-1380815

  日期：——

  A novel copper-catalyzed cascade synthesis of thiazolidine-2-thiones from N-(2-bromoallyl) amines and carbon disulfide has been developed. The procedure combines carbamodithioic acid formation and copper-catalyzed intramolecular S-vinylation in one sequence. By elevating the temperature, the one-pot reaction efficiently affords thiazole-2(3H)-thiones in moderate to good yields.