allyl β-iodoacrylate | 652975-98-9

• 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: allyl β-iodoacrylate
• 英文别名: (E)-allyl 3-iodo-acrylate；(E)-allyl 3-iodoacrylate；prop-2-enyl (E)-3-iodoprop-2-enoate
• CAS: 652975-98-9
• 化学式: C₆H₇IO₂
• 分子量: 238.025
• InChiKey: WGGRCAMYVSPHHU-ONEGZZNKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-甲基甲酰胺 、 allyl β-iodoacrylate 在 rubidium carbonate 、 tetrakis(actonitrile)copper(I) hexafluorophosphate 、 3,4,7,8-四甲基-1,10-菲罗啉 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 12.0h， 以77%的产率得到prop-2-enyl (E)-3-[formyl(methyl)amino]prop-2-enoate
  参考文献：
  名称：

  Copper-Mediated Synthesis of N-Acyl Vinylogous Carbamic Acids and Derivatives:  Synthesis of the Antibiotic CJ-15,801

  摘要：

  Copper(I)-mediated C-N bond formation has been employed to prepare both N-acyl vinylogous carbamic acids and ureas. The novel N-acyl vinylogous carbamic acid antibiotic, CJ-15,801, was synthesized using this methodology.

  DOI：

  10.1021/ol0360041
• 作为产物：
  描述：

  (E)-3-碘-2-丙酸 、 烯丙醇 在 4-二甲氨基吡啶 、 4-(dimethylamino)pyridine hydrochloride 、 N,N'-二异丙基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以92%的产率得到allyl β-iodoacrylate
  参考文献：
  名称：

  Copper-Mediated Synthesis of N-Acyl Vinylogous Carbamic Acids and Derivatives:  Synthesis of the Antibiotic CJ-15,801

  摘要：

  Copper(I)-mediated C-N bond formation has been employed to prepare both N-acyl vinylogous carbamic acids and ureas. The novel N-acyl vinylogous carbamic acid antibiotic, CJ-15,801, was synthesized using this methodology.

  DOI：

  10.1021/ol0360041

文献信息

• A flexible route to immunosuppressive agent FR252921. Asymmetric total synthesis of its (13R,14R,19R)-isomer
  作者：Shouyun Yu、Feng Liu、Dawei Ma

  DOI：10.1016/j.tetlet.2006.09.169

  日期：2006.12

  A flexible route to the proposed structure of FR252921, a novel immunosuppressive agent, is developed. The key elements include the assembly of its two P-hydroxy acid residues via asymmetric aldol condensation of N-acylthiazolidinethinones with aldehydes, and its triene part via a CuI/N,N-dimethylglycine catalyzed Sonogashira coupling and subsequent isomerization. Using this strategy (13R,14R,19R)-FR252921 is elaborated. (c) 2006 Elsevier Ltd. All rights reserved.
• Copper-Catalyzed Vinylation of Hydrazides. A Regioselective Entry to Highly Substituted Pyrroles
  作者：Marta Rodríguez Rivero、Stephen L. Buchwald

  DOI：10.1021/ol062978s

  日期：2007.3.1

  A modular route to highly substituted pyrroles has been developed. This transformation consists of two sequential copper-catalyzed vinylations of bis-Boc-hydrazine followed by thermal rearrangement/cyclization. A wide variety of functionalized pyrroles can be prepared in a selective manner from simple and easily accessible precursors.
• CuI/<i>N</i>,<i>N</i>-Dimethylglycine-Catalyzed Coupling of Vinyl Halides with Amides or Carbamates
  作者：Xianhua Pan、Qian Cai、Dawei Ma

  DOI：10.1021/ol049464i

  日期：2004.5.1

  The Cul-catalyzed coupling reaction of vinyl halides with amides or carbamates proceeds well at room temperature to 80 degreesC in dioxane to give enamides using NN-dimethylglycine as the promoter and Cs2CO3 as the base. The geometry of the C-C double bond is retained during the reaction course.
• US9193674B2
  申请人：——

  公开号：US9193674B2

  公开（公告）日：2015-11-24
• Copper-Mediated Synthesis of <i>N</i>-Acyl Vinylogous Carbamic Acids and Derivatives:  Synthesis of the Antibiotic CJ-15,801
  作者：Chong Han、Ruichao Shen、Shun Su、John A. Porco

  DOI：10.1021/ol0360041

  日期：2004.1.1

  Copper(I)-mediated C-N bond formation has been employed to prepare both N-acyl vinylogous carbamic acids and ureas. The novel N-acyl vinylogous carbamic acid antibiotic, CJ-15,801, was synthesized using this methodology.