N-(but-3-enyl)-N-(1-isopropyl-but-3-enyl)carbamic acid phenyl ester | 342775-49-9

• 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-(but-3-enyl)-N-(1-isopropyl-but-3-enyl)carbamic acid phenyl ester
• 英文别名: phenyl N-but-3-enyl-N-(2-methylhex-5-en-3-yl)carbamate
• CAS: 342775-49-9
• 化学式: C₁₈H₂₅NO₂
• 分子量: 287.402
• InChiKey: XRSLUCBKMZVEQR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  21
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(but-3-enyl)-N-(1-isopropyl-but-3-enyl)carbamic acid phenyl ester 在 Grubbs catalyst first generation 作用下， 以 二氯甲烷 为溶剂， 以98%的产率得到2-isopropyl-2,3,6,7-tetrahydroazepine-1-carboxylic acid phenyl ester
  参考文献：
  名称：

  Synthesis of N,N-Bis(3-butenyl)amines from 2-Azaallyl Dication Synthetic Equivalents and Conversion to 2,3,6,7-Tetrahydroazepines by Ring-Closing Metathesis

  摘要：

  [GRAPHICS]N,N-Bis(3-butenyl)amines can be prepared by the double allylation of either (2-azaallyl)stannanes or (2-azaallyl)nitriles, both of which thereby act as synthetic equivalents to amine alpha,alpha'-dications (2-azaallyl dications). Allylmagnesium bromide is the reagent of choice for the double allylation of both substrates, although allyllithium also effects the double allylation of (2-azaallyl)nitriles. Ring-closing metathesis can be performed on the N-protected amines, or with in situ protonation, on the free amines to provide 2,3,6,7-tetrahydroazepines. (2-Azaallyl)nitriles can also be monoallylated to provide N-(3-butenyl)-aminonitriles, whereas the double allylation of (2-azaallyl)stannanes cannot be stopped at monoallylation. (2-Azaallyl)silanes undergo monoallylation to give N-(3-butenyl)aminosilanes but do not undergo double allylation.

  DOI：

  10.1021/jo060173s
• 作为产物：
  描述：

  N-[(tri-n-butylstannyl)methyl]2-methylpropanimine 、 氯甲酸苯酯 、 烯丙基溴化镁 以 四氢呋喃 、 乙醚 为溶剂， 反应 0.5h， 以80%的产率得到N-(but-3-enyl)-N-(1-isopropyl-but-3-enyl)carbamic acid phenyl ester
  参考文献：
  名称：

  Double Allylation Reactions of (2-Azaallyl)stannanes:  Synthesis of N,N-Bis(3-butenyl)amines and Their Conversion to 2,3,6,7-Tetrahydroazepines via Ring-Closing Metathesis

  摘要：

  [GRAPHICS]Treatment of (2-azaallyl)stannanes (i) with 2.2 equiv of allylmagnesium bromide afforded good yields of N,N-bis(3-butenyl)amines derivatives (ii), which were subjected to ring-closing metathesis ts afford 2,3,6,7 tetrahydroazepines (iii), Thus, (2-azaallyl)stannanes are the synthetic equivalents of amine alpha,alpha ' -dications.

  DOI：

  10.1021/ol015711w

文献信息

• Synthesis of <i>N</i>,<i>N</i>-Bis(3-butenyl)amines from 2-Azaallyl Dication Synthetic Equivalents and Conversion to 2,3,6,7-Tetrahydroazepines by Ring-Closing Metathesis
  作者：William H. Pearson、Aaron Aponick、Amber L. Dietz

  DOI：10.1021/jo060173s

  日期：2006.4.1

  [GRAPHICS]N,N-Bis(3-butenyl)amines can be prepared by the double allylation of either (2-azaallyl)stannanes or (2-azaallyl)nitriles, both of which thereby act as synthetic equivalents to amine alpha,alpha'-dications (2-azaallyl dications). Allylmagnesium bromide is the reagent of choice for the double allylation of both substrates, although allyllithium also effects the double allylation of (2-azaallyl)nitriles. Ring-closing metathesis can be performed on the N-protected amines, or with in situ protonation, on the free amines to provide 2,3,6,7-tetrahydroazepines. (2-Azaallyl)nitriles can also be monoallylated to provide N-(3-butenyl)-aminonitriles, whereas the double allylation of (2-azaallyl)stannanes cannot be stopped at monoallylation. (2-Azaallyl)silanes undergo monoallylation to give N-(3-butenyl)aminosilanes but do not undergo double allylation.
• Double Allylation Reactions of (2-Azaallyl)stannanes:  Synthesis of <i>N,N</i>-Bis(3-butenyl)amines and Their Conversion to 2,3,6,7-Tetrahydroazepines via Ring-Closing Metathesis
  作者：William H. Pearson、Aaron Aponick

  DOI：10.1021/ol015711w

  日期：2001.5.1

  [GRAPHICS]Treatment of (2-azaallyl)stannanes (i) with 2.2 equiv of allylmagnesium bromide afforded good yields of N,N-bis(3-butenyl)amines derivatives (ii), which were subjected to ring-closing metathesis ts afford 2,3,6,7 tetrahydroazepines (iii), Thus, (2-azaallyl)stannanes are the synthetic equivalents of amine alpha,alpha ' -dications.