(R,E)-2,2-dimethyl-3-(tert-butoxycarbonyl)-4-(2-iodoethen-1-yl)oxazolidine

• 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: (R,E)-2,2-dimethyl-3-(tert-butoxycarbonyl)-4-(2-iodoethen-1-yl)oxazolidine
• 英文别名: tert-butyl (4R)-4-[(E)-2-iodoethenyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
• 化学式: C₁₂H₂₀INO₃
• 分子量: 353.2
• InChiKey: QVNCTWCURZHEDS-XCODYQFDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 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：

  (R)-2,2-Dimethyl-4-((E)-2-tributylstannanyl-vinyl)-oxazolidine-3-carboxylic acid tert-butyl ester 在 碘 作用下， 以 氯仿 为溶剂， 反应 3.0h， 以54%的产率得到(R,E)-2,2-dimethyl-3-(tert-butoxycarbonyl)-4-(2-iodoethen-1-yl)oxazolidine
  参考文献：
  名称：

  Synthetic Elaboration of the Side Chain of (R)-2,2-Dimethyl-3-(tert-butoxycarbonyl)-4-ethynyloxazolidine:  A New Regio- and Stereoselective Strategy to δ-Functionalized β-Amino Alcohols

  摘要：

  An investigation of the reactivity of ethynyloxazolidine 2 is presented. Functionalization at the acetylenic position has been found to occur very easily using the mild Sonogashira conditions. Addition of tributyltin cuprate 1 provided the corresponding stannylated (E)-ethenyloxazolidine 3, a new chiral building block which has been reacted with electrophiles under Pd catalysis. The reaction sequence occurred without racemization and showed an easy and mild procedure for the regio- and stereoselective synthesis of unsaturated amino alcohols.

  DOI：

  10.1021/jo970619s

文献信息

• An Expedient Total Synthesis of Chivosazole F: an Actin-Binding Antimitotic Macrolide from the Myxobacterium <i>Sorangium Cellulosum</i>
  作者：Simon Williams、Jialu Jin、S. B. Jennifer Kan、Mungyuen Li、Lisa J. Gibson、Ian Paterson

  DOI：10.1002/anie.201610636

  日期：2017.1.9

  A unified strategy for the chemical synthesis of the chivosazoles is described. This strategy is based on two closely related approaches involving the late‐stage installation of the isomerization‐prone (2Z,4E,6Z,8E)‐tetraenoate motif, and an expedient fragment‐assembly procedure. The result is a highly convergent total synthesis of chivosazole F through the orchestration of three mild Pd/Cu‐mediated

  描述了用于化学合成齐沃唑的统一策略。该策略基于两种密切相关的方法，包括易于后期安装的易异构化（2 Z，4 E，6 Z，8 E）-四烯酸酯基序，以及便捷的片段组装程序。结果是通过三个轻度Pd / Cu介导的Stille交叉偶合反应的编排，高度收敛地合成了Chivosazole F，包括使用一锅法，定点选择，三组分法以及可控的方法。安装所需的烯烃几何形状。
• Synthetic Elaboration of the Side Chain of (<i>R</i>)-2,2-Dimethyl-3-(<i>tert</i>-butoxycarbonyl)-4-ethynyloxazolidine:  A New Regio- and Stereoselective Strategy to δ-Functionalized β-Amino Alcohols
  作者：Gianna Reginato、Alessandro Mordini、Massimo Caracciolo

  DOI：10.1021/jo970619s

  日期：1997.9.1

  An investigation of the reactivity of ethynyloxazolidine 2 is presented. Functionalization at the acetylenic position has been found to occur very easily using the mild Sonogashira conditions. Addition of tributyltin cuprate 1 provided the corresponding stannylated (E)-ethenyloxazolidine 3, a new chiral building block which has been reacted with electrophiles under Pd catalysis. The reaction sequence occurred without racemization and showed an easy and mild procedure for the regio- and stereoselective synthesis of unsaturated amino alcohols.