(6-iodo-2,2-dimethylchromen-5-yl) N,N-diethylcarbamate | 238736-93-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (6-iodo-2,2-dimethylchromen-5-yl) N,N-diethylcarbamate
• CAS: 238736-93-1
• 化学式: C₁₆H₂₀INO₃
• 分子量: 401.244
• InChiKey: YHNCQBNUDLZLAB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (6-iodo-2,2-dimethylchromen-5-yl) N,N-diethylcarbamate 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 bis(triphenylphosphine) palladium (Il) acetate 甲醇 、 potassium carbonate 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 50.0h， 生成 [2,2-dimethyl-6-(6-propan-2-yloxy-1-benzofuran-2-yl)chromen-5-yl] N,N-diethylcarbamate
  参考文献：
  名称：

  Directed Metalation Linked to Transition Metal Catalyzed Cascade Reactions: Two Total Syntheses of Plicadin, the Alleged Coumestan fromPsoralea plicata

  摘要：

  The oxygen-rich heterocyclic compound 1-which was proposed to be the structure of plicadin, the alleged naturally occurring coumestan from the herb Psoralea plicata-was synthesized by the rational combinations of directed ortho and remote metalation reactions with cascades of Negishi, Sonogashira, Castro-Stephens, and carbamoyl Baker-Venkataraman reactions.

  DOI：

  10.1002/(sici)1521-3773(19990517)38:10<1435::aid-anie1435>3.0.co;2-b
• 作为产物：
  描述：

  1,3-Bis(N,N-diethylcarbamoyl)benzene 在 叔丁基锂 、 仲丁基锂 作用下， 以 四氢呋喃 、 环己烷 、 正戊烷 为溶剂， 反应 10.25h， 生成 (6-iodo-2,2-dimethylchromen-5-yl) N,N-diethylcarbamate
  参考文献：
  名称：

  Directed Metalation Linked to Transition Metal Catalyzed Cascade Reactions: Two Total Syntheses of Plicadin, the Alleged Coumestan fromPsoralea plicata

  摘要：

  The oxygen-rich heterocyclic compound 1-which was proposed to be the structure of plicadin, the alleged naturally occurring coumestan from the herb Psoralea plicata-was synthesized by the rational combinations of directed ortho and remote metalation reactions with cascades of Negishi, Sonogashira, Castro-Stephens, and carbamoyl Baker-Venkataraman reactions.

  DOI：

  10.1002/(sici)1521-3773(19990517)38:10<1435::aid-anie1435>3.0.co;2-b

文献信息

• An Efficient Synthesis of Coumestrol and Coumestans by Iodocyclization and Pd-Catalyzed Intramolecular Lactonization
  作者：Tuanli Yao、Dawei Yue、Richard C. Larock

  DOI：10.1021/jo0517038

  日期：2005.11.1

  The iodocyclization of acetoxy-containing 2-(1-alkynyl)anisoles and subsequent direct palladium-catalyzed carbonylation/lactonization provide an efficient route to naturally occurring coumestan and coumestrol, and their related analogues.