2-iodo-1,3-phenylene bis(2,2-dimethylpropanoate) | 1369625-91-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: 2-iodo-1,3-phenylene bis(2,2-dimethylpropanoate)
• CAS: 1369625-91-1
• 化学式: C₁₆H₂₁IO₄
• 分子量: 404.245
• InChiKey: BTCKVVQWIZTNPY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.19
• 重原子数：
  21.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-iodo-1,3-phenylene bis(2,2-dimethylpropanoate) 在 (1,5-cyclooctadiene)(methoxy)iridium(I) dimer 、 ammonium hexafluorophosphate 、 palladium(II) trifluoroacetate 、 3,4,7,8-四甲基-1,10-菲罗啉 、 硫酸 、 水 、 (S)-4-叔丁基-2-(2-氮苯基)恶唑啉 作用下， 以 四氢呋喃 、 乙酸乙酯 、 1,2-二氯乙烷 为溶剂， 反应 133.0h， 生成 (R)-2-iodo-5-(1-methyl-3-oxocyclohexyl)-1,3-phenylene bis(2,2-dimethylpropanoate)
  参考文献：
  名称：

  A Catalytic, Enantioselective Formal Synthesis of (+)-Dichroanone and (+)-Taiwaniaquinone H

  摘要：

  A catalytic, enantioselective formal synthesis of (+)-dichroanone and (+)-taiwaniaquinone H is reported. The all-carbon quaternary stereocenter was constructed by asymmetric conjugate addition catalyzed by a palladium(II) (S)-tert-butylpyridinooxazoline complex. The unexpected formation of a [3.2.1] bicyclic intermediate required the identification of a new route. Analysis of the Hammett constants for para-substituted arenes enabled the rational design of a highly enantioselective conjugate addition substrate that led to the completion of the formal synthesis.

  DOI：

  10.1021/ol5031537
• 作为产物：
  描述：

  2-[diisopropyl(pyrimidin-2-yl)silyl]-1,3-phenylene bis(2,2-dimethylpropanoate) 在 氢氟酸 、 N-碘代丁二酰亚胺 、 silver fluoride 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.0h， 以95%的产率得到2-iodo-1,3-phenylene bis(2,2-dimethylpropanoate)
  参考文献：
  名称：

  Double-Fold C–H Oxygenation of Arenes Using PyrDipSi: a General and Efficient Traceless/Modifiable Silicon-Tethered Directing Group

  摘要：

  The efficient Pd-catalyzed double-fold C-H oxygenation of arenes into resorcinols using the newly developed 2-pyrimidyldiisopropylsilyl (PyrDipSi) directing group is described. Its use allows for the sequential introduction of OAc and OPiv groups in a one-pot manner to produce orthogonally protected resorcinol derivatives. The PyrDipSi group is superior to the previously developed 2-pyridyldiisopropylsilyl (PyDipSi) group, as it is efficient for monooxygenation of ortho-substituted arenes. Notably, the PyrDipSi group can be easily installed into arene molecules and can be easily removed or modified after the oxygenation reaction.

  DOI：

  10.1021/ja3010545