dimethylcarbamic acid 2-iodo-3-nitrophenyl ester | 916445-83-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: dimethylcarbamic acid 2-iodo-3-nitrophenyl ester
• 英文别名: (2-iodo-3-nitrophenyl) N,N-dimethylcarbamate
• CAS: 916445-83-5
• 化学式: C₉H₉IN₂O₄
• 分子量: 336.086
• InChiKey: ZIERWOHVNJBSPJ-UHFFFAOYSA-N

物化性质

• 熔点：
  125-126 °C
• 沸点：
  372.9±42.0 °C(Predicted)
• 密度：
  1.819±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  75.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  dimethylcarbamic acid 2-iodo-3-nitrophenyl ester 在 palladium diacetate 三甲基铝 、 sodium acetate 、 铁粉 、 sodium hydride 、 溶剂黄146 、 N,N-二异丙基乙胺 、 三(邻甲基苯基)磷 、 sodium iodide 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 、 二氯甲烷 、 N,N-二甲基乙酰胺 为溶剂， 90.0 ℃ 、101.33 kPa 条件下， 反应 28.0h， 生成 [4-dimethylcarbamoyloxy-3-(2-methoxymethoxyethyl)-1-methyl-2-oxo-2,3-dihydro-1H-indol-3-yl]-[2-(4-methoxyphenoxymethyl)phenyl]acetic acid methyl ester
  参考文献：
  名称：

  Synthetic Studies on Perophoramidine and the Communesins:  Construction of the Vicinal Quaternary Stereocenters

  摘要：

  An efficient synthetic strategy for installation of the two vicinal quaternary carbon centers of the communesins is reported. Key steps include the O-allylation/Claisen rearrangement of spirolactone systems, which are formed by tandem intramolecular Heck cyclization/carbonylation. Substituent and solvent effects on the stereochemical outcome of the Claisen rearrangements have been examined. The stereochemical assignment of the allyl spirolactone previously reported as 17 has now been revised to 31, which has the communesin relative configuration at the quaternary carbons. Key C-allyl spirolactone 59 bearing functional handles required for the communesin core has been constructed with a 9.8:1 diastereomer ratio.

  DOI：

  10.1021/jo061660a
• 作为产物：
  描述：

  2-碘-3-硝基苯酚 、 二甲氨基甲酰氯 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以94%的产率得到dimethylcarbamic acid 2-iodo-3-nitrophenyl ester
  参考文献：
  名称：

  Synthetic Studies on Perophoramidine and the Communesins:  Construction of the Vicinal Quaternary Stereocenters

  摘要：

  An efficient synthetic strategy for installation of the two vicinal quaternary carbon centers of the communesins is reported. Key steps include the O-allylation/Claisen rearrangement of spirolactone systems, which are formed by tandem intramolecular Heck cyclization/carbonylation. Substituent and solvent effects on the stereochemical outcome of the Claisen rearrangements have been examined. The stereochemical assignment of the allyl spirolactone previously reported as 17 has now been revised to 31, which has the communesin relative configuration at the quaternary carbons. Key C-allyl spirolactone 59 bearing functional handles required for the communesin core has been constructed with a 9.8:1 diastereomer ratio.

  DOI：

  10.1021/jo061660a