3-[(Z)-4-phenylbut-1-enyl]oxazolidin-2-one | 1190789-05-9

• 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)-4-phenylbut-1-enyl]oxazolidin-2-one
• 英文别名: 3-[(Z)-4-phenylbut-1-enyl]-1,3-oxazolidin-2-one
• CAS: 1190789-05-9
• 化学式: C₁₃H₁₅NO₂
• 分子量: 217.268
• InChiKey: MOWGPKGVZTYGBY-UITAMQMPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-(4-phenylbut-1-yn-1-yl)oxazolidin-2-one 在 chloro(1,5-cyclooctadiene)rhodium(I) dimer 、 三(2-噻吩基)膦 、 diethylzinc 作用下， 以 四氢呋喃 为溶剂， 生成 3-[(Z)-4-phenylbut-1-enyl]oxazolidin-2-one 、 (E)-3-(4-phenylbut-1-en-1-yl)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

• Ligand-Controlled Regiodivergent Hydroformylation of Ynamides: A Stereospecific and Regioselective Access to 2- and 3-Aminoacroleins
  作者：Patrick Wagner、Morgan Donnard、Nicolas Girard

  DOI：10.1021/acs.orglett.9b03566

  日期：2019.11.1

  The rhodium-catalyzed hydroformylation of ynamides is described and gives selective access to 2- or 3-aminoacrolein derivatives. The regioselectivity of this carbonylation can be completely controlled at will thanks to the nature of the ligand used. This represents the first example of regiodivergent alkyne hydroformylation. The influence of the substituents on the different positions of the ynamide

  描述了铑催化的酰胺的加氢甲酰化反应，可选择性地使用2-或3-氨基丙烯醛衍生物。由于所用配体的性质，可以任意地完全控制该羰基化的区域选择性。这代表了区域发散性炔烃加氢甲酰化的第一个例子。已经研究了取代基对炔基酰胺不同位置的影响，并且看来该反应可耐受多种官能团。
• (NHC-olefin)-nickel(0) nanoparticles as catalysts for the (<i>Z</i>)-selective semi-hydrogenation of alkynes and ynamides
  作者：Marta G. Avello、Stéphane Golling、Lai Truong-Phuoc、Loïc Vidal、Thierry Romero、Vasiliki Papaefthimiou、Nathalie Gruber、Michael J. Chetcuti、Frédéric R. Leroux、Morgan Donnard、Vincent Ritleng、Cuong Pham-Huu、Christophe Michon

  DOI：10.1039/d2cc05302k

  日期：——

  Nickel(0)-NHC nanoparticles bearing cinnamyl moieties catalyse effectively (Z)-selective semi-hydrogenations.

  镍(0)-NHC纳米颗粒带有肉桂基团，有效催化(Z)-选择性半氢化反应。
• 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.