benzyl (1-buta-2,3-dienylcyclohexylmethyl)carbamate

• 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: benzyl (1-buta-2,3-dienylcyclohexylmethyl)carbamate
• 化学式: C₁₉H₂₅NO₂
• 分子量: 299.413
• InChiKey: BOOWZAQTCVAZJT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  benzyl (1-buta-2,3-dienylcyclohexylmethyl)carbamate 在 氯(二甲基硫化)金(I) 、 (R,R)-(-)-(2,6-diphenyl-3,5-dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl) bis(1-phenylethyl)amine 、 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 反应 23.0h， 生成 benzyl-3-vinyl-2-aza-spiro[4.5]decane-2-carboxylate 、 benzyl-3-vinyl-2-aza-spiro[4.5]decane-2-carboxylate
  参考文献：
  名称：

  Asymmetric Intramolecular Hydroamination of Allenes using Mononuclear Gold Catalysts

  摘要：

  The intramolecular gold-catalyzed asymmetric hydroamination of allenes was studied by screening a series of mononuclear gold(I) and -(III) complexes in combination with silver salts. Among the various chiral monophosphine and diaminocarbene ligands tried, the best catalysts arose from mononuclear gold(I) complexes synthesized from BINOL-based phosphoramidite ligands. The latest were improved by addition of bulky substituents at specific positions of the BINOL scaffold. The resulting gold(I) complexes were combined with selected silver salts to afford efficient catalysts for intramolecular hydroamination of allenes at room temperature or below, with good conversions and enantioselectivities.

  DOI：

  10.1021/om4009058
• 作为产物：
  描述：

  1-(prop-2-yn-1-yl)cyclohexanecarbonitrile 在 二异丁基氢化铝 、 碳酸氢钠 、 二异丙胺 、 copper(I) bromide 作用下， 以 1,4-二氧六环 、 乙醚 、 乙醇 、 水 、 甲苯 为溶剂， 生成 benzyl (1-buta-2,3-dienylcyclohexylmethyl)carbamate
  参考文献：
  名称：

  金（I）催化的N-烯丙基氨基甲酸酯的对映选择性加氢胺化。

  摘要：

  用[（S）-1] Au2Cl2 [（S）-1 =（S）-3,5-t-Bu-4-MeO）1：2催化混合物处理N-4,5-己二烯基氨基甲酸酯2a [-MeOBIPHEP]和AgClO4在-40°C的间二甲苯中放置24小时，从而以97％的收率分离出2-乙烯基吡咯烷3a，ee值为81％。金（I）催化的对映选择性氢化胺化对于许多氨基甲酸酯基团和可承受的烯基部分的末端去位取代作用是有效的。

  DOI：

  10.1021/ol071108n

文献信息

• Gold(I)-Catalyzed Enantioselective Hydroamination of <i>N</i>-Allenyl Carbamates
  作者：Zhibin Zhang、Christopher F. Bender、Ross A. Widenhoefer

  DOI：10.1021/ol071108n

  日期：2007.7.1

  mixture of [(S)-1]Au2Cl2 [(S)-1 = (S)-3,5-t-Bu-4-MeO-MeOBIPHEP] and AgClO4 in m-xylene at -40 degrees C for 24 h led to isolation of 2-vinylpyrrolidine 3a in 97% yield with 81% ee. Gold(I)-catalyzed enantioselective hydroamination was effective for a number of carbamate groups and tolerated terminal disubstitutution of the allenyl moiety.

  用[（S）-1] Au2Cl2 [（S）-1 =（S）-3,5-t-Bu-4-MeO）1：2催化混合物处理N-4,5-己二烯基氨基甲酸酯2a [-MeOBIPHEP]和AgClO4在-40°C的间二甲苯中放置24小时，从而以97％的收率分离出2-乙烯基吡咯烷3a，ee值为81％。金（I）催化的对映选择性氢化胺化对于许多氨基甲酸酯基团和可承受的烯基部分的末端去位取代作用是有效的。
• Asymmetric Intramolecular Hydroamination of Allenes using Mononuclear Gold Catalysts
  作者：Christophe Michon、Florian Medina、Marc-Antoine Abadie、Francine Agbossou-Niedercorn

  DOI：10.1021/om4009058

  日期：2013.10.14

  The intramolecular gold-catalyzed asymmetric hydroamination of allenes was studied by screening a series of mononuclear gold(I) and -(III) complexes in combination with silver salts. Among the various chiral monophosphine and diaminocarbene ligands tried, the best catalysts arose from mononuclear gold(I) complexes synthesized from BINOL-based phosphoramidite ligands. The latest were improved by addition of bulky substituents at specific positions of the BINOL scaffold. The resulting gold(I) complexes were combined with selected silver salts to afford efficient catalysts for intramolecular hydroamination of allenes at room temperature or below, with good conversions and enantioselectivities.