cyclopent-2-enyl carbamate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: cyclopent-2-enyl carbamate
• 英文别名: Cyclopent-2-en-1-yl carbamate
• 化学式: C₆H₉NO₂
• mdl: MFCD19213462
• 分子量: 127.143
• InChiKey: NKTJKLHLQUAHSJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  cyclopent-2-enyl carbamate 、 碘苯二乙酸 在 辛酸铑 、 magnesium oxide 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以50%的产率得到(3aS*,4R*,6aR*)-2-oxohexahydro-2H-cyclopenta[d]oxazol-4-yl acetate
  参考文献：
  名称：

  Substrate scope and stereocontrol in the Rh(II)-catalysed oxyamination of allylic carbamates

  摘要：

  Application of a modified Du Bois protocol for rhodium-stabilised nitrenoid generation to a variety of allylic carbamates results in 4-acetoxymethyl-1,3-oxazolidin-2-one derivatives with moderate to high levels of stereocontrol. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.06.051
• 作为产物：
  描述：

  2-环戊烯-1-醇 在 水 、 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 cyclopent-2-enyl carbamate
  参考文献：
  名称：

  Substrate scope and stereocontrol in the Rh(II)-catalysed oxyamination of allylic carbamates

  摘要：

  Application of a modified Du Bois protocol for rhodium-stabilised nitrenoid generation to a variety of allylic carbamates results in 4-acetoxymethyl-1,3-oxazolidin-2-one derivatives with moderate to high levels of stereocontrol. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.06.051

文献信息

• The Tethered Aminohydroxylation (TA) of Cyclic Allylic Carbamates
  作者：Timothy J. Donohoe、Peter D. Johnson、Andrew Cowley、Martine Keenan

  DOI：10.1021/ja0276117

  日期：2002.11.1

  The tethered aminohydroxylation of cyclic allylic carbamates is described using catalytic amounts of potassium osmate. The mechanism of reaction involves formation of an imido-osmium complex which adds intramolecularly to alkenes with complete control of both regio- and stereoselectivity: the formation of syn-aminodiol motifs is now straightforward using this chemistry. Proof of the mechanism was obtained with an X-ray crystal structure of an azaglycolate osmate ester intermediate.
• Substrate scope and stereocontrol in the Rh(II)-catalysed oxyamination of allylic carbamates
  作者：William P. Unsworth、Scott G. Lamont、Jeremy Robertson

  DOI：10.1016/j.tet.2014.06.051

  日期：2014.10

  Application of a modified Du Bois protocol for rhodium-stabilised nitrenoid generation to a variety of allylic carbamates results in 4-acetoxymethyl-1,3-oxazolidin-2-one derivatives with moderate to high levels of stereocontrol. (C) 2014 Elsevier Ltd. All rights reserved.