3-[(Z)-5-(tert-butyldimethylsilyloxy)pent-1-enyl]oxazolidin-2-one | 1190789-34-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: 3-[(Z)-5-(tert-butyldimethylsilyloxy)pent-1-enyl]oxazolidin-2-one
• 英文别名: 3-[(Z)-5-[tert-butyl(dimethyl)silyl]oxypent-1-enyl]-1,3-oxazolidin-2-one
• CAS: 1190789-34-4
• 化学式: C₁₄H₂₇NO₃Si
• 分子量: 285.459
• InChiKey: KIQARMPSNBHECD-CLFYSBASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.75
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-(5-tert-butyldimethylsilyloxypent-1-ynyl)oxazolidin-2-one 、 diethylzinc 在 chloro(1,5-cyclooctadiene)rhodium(I) dimer 、 三(2-呋喃基)膦 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 生成 3-[(Z)-5-(tert-butyldimethylsilyloxy)pent-1-enyl]oxazolidin-2-one 、 3-[5-[tert-butyl(dimethyl)silyl]oxy-2-ethylpent-1-enyl]-1,3-oxazolidin-2-one
  参考文献：
  名称：

  Preparation of Multisubstituted Enamides via Rhodium-Catalyzed Carbozincation and Hydrozincation of Ynamides

  摘要：

  Rhodium-catalyzed carbozincation of ynamides using diorganozinc reagents or functionalized organozinc halides is described. Using a tri(2-furyl)phosphine-modified rhodium catalyst, the reaction course is altered to hydrozincation when diethylzinc is employed as the organozinc reagent. Trapping of the alkenylzinc intermediates produced in these reactions in further functionalization reactions is possible. Collectively, these processes enable access to a range of multisubstituted enamides in stereo- and regiocontrolled fashion.

  DOI：

  10.1021/jo901658v

文献信息

• Preparation of Multisubstituted Enamides via Rhodium-Catalyzed Carbozincation and Hydrozincation of Ynamides
  作者：Benoit Gourdet、Mairi E. Rudkin、Ciorsdaidh A. Watts、Hon Wai Lam

  DOI：10.1021/jo901658v

  日期：2009.10.16

  Rhodium-catalyzed carbozincation of ynamides using diorganozinc reagents or functionalized organozinc halides is described. Using a tri(2-furyl)phosphine-modified rhodium catalyst, the reaction course is altered to hydrozincation when diethylzinc is employed as the organozinc reagent. Trapping of the alkenylzinc intermediates produced in these reactions in further functionalization reactions is possible. Collectively, these processes enable access to a range of multisubstituted enamides in stereo- and regiocontrolled fashion.