6-oxocyclohex-1-enyl N,N-diisopropylcarbamate | 1174755-43-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-oxocyclohex-1-enyl N,N-diisopropylcarbamate
• 英文别名: (6-oxocyclohexen-1-yl) N,N-di(propan-2-yl)carbamate
• CAS: 1174755-43-1
• 化学式: C₁₃H₂₁NO₃
• 分子量: 239.315
• InChiKey: FZGOUYWINKKQDW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-oxocyclohex-1-enyl N,N-diisopropylcarbamate 、 diethylzinc 在 (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine 、 copper(II) bis(trifluoromethanesulfonate) 、 甲酸 作用下， 以 正己烷 、 甲苯 、 甲醇 为溶剂， 反应 16.0h， 以81%的产率得到2-ethyl-6-oxocyclohexyl N,N-diisopropylcarbamate
  参考文献：
  名称：

  Copper-catalyzed asymmetric addition of Et2Zn to 2-cyclohexen-1-one and 2-carbamoyloxy-2-cyclohexen-1-one with phosphoramidite, phosphite, and bidentate phosphite–oxazoline ligands

  摘要：

  New biphenol-backboned phosphite-oxazoline bidentate ligands were synthesized and applied in the copper-catalyzed asymmetric conjugate additions on 2-cyclohexen-1-one with Et2Zn. In these reactions, the non-chiral oxazoline unit has demonstrated significant impact on the enantioselectivity. 2-Carbamoyloxy-2-cyclohexen-1-one is a new alpha-oxygenated cyclic enone substrate and was synthesized and applied to the aforementioned addition with certain phosphoramidite, phosphite, and the new bidentate ligands. Good ee has been obtained on this substrate. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.03.017
• 作为产物：
  描述：

  二异丙基甲胺酰氯 、 1,2-环己二酮 在 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 4.0h， 以54%的产率得到6-oxocyclohex-1-enyl N,N-diisopropylcarbamate
  参考文献：
  名称：

  Copper-catalyzed asymmetric addition of Et2Zn to 2-cyclohexen-1-one and 2-carbamoyloxy-2-cyclohexen-1-one with phosphoramidite, phosphite, and bidentate phosphite–oxazoline ligands

  摘要：

  New biphenol-backboned phosphite-oxazoline bidentate ligands were synthesized and applied in the copper-catalyzed asymmetric conjugate additions on 2-cyclohexen-1-one with Et2Zn. In these reactions, the non-chiral oxazoline unit has demonstrated significant impact on the enantioselectivity. 2-Carbamoyloxy-2-cyclohexen-1-one is a new alpha-oxygenated cyclic enone substrate and was synthesized and applied to the aforementioned addition with certain phosphoramidite, phosphite, and the new bidentate ligands. Good ee has been obtained on this substrate. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.03.017

文献信息

• Copper-catalyzed asymmetric addition of Et2Zn to 2-cyclohexen-1-one and 2-carbamoyloxy-2-cyclohexen-1-one with phosphoramidite, phosphite, and bidentate phosphite–oxazoline ligands
  作者：Yue-Lei Chen、Roland Fröhlich、Dieter Hoppe

  DOI：10.1016/j.tetasy.2009.03.017

  日期：2009.6

  New biphenol-backboned phosphite-oxazoline bidentate ligands were synthesized and applied in the copper-catalyzed asymmetric conjugate additions on 2-cyclohexen-1-one with Et2Zn. In these reactions, the non-chiral oxazoline unit has demonstrated significant impact on the enantioselectivity. 2-Carbamoyloxy-2-cyclohexen-1-one is a new alpha-oxygenated cyclic enone substrate and was synthesized and applied to the aforementioned addition with certain phosphoramidite, phosphite, and the new bidentate ligands. Good ee has been obtained on this substrate. (C) 2009 Elsevier Ltd. All rights reserved.