(((7R,8S)-8-((E)-but-2-en-1-yl)-3-methoxy-4,7-dimethyl-4,4a,5,6,7,8-hexahydro-3H-isochromen-3-yl)oxy)-triisopropylsilane | 1393603-21-8

• 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: (((7R,8S)-8-((E)-but-2-en-1-yl)-3-methoxy-4,7-dimethyl-4,4a,5,6,7,8-hexahydro-3H-isochromen-3-yl)oxy)-triisopropylsilane
• 英文别名: [(7R,8S)-8-[(E)-but-2-enyl]-3-methoxy-4,7-dimethyl-4,4a,5,6,7,8-hexahydroisochromen-3-yl]oxy-tri(propan-2-yl)silane
• CAS: 1393603-21-8
• 化学式: C₂₅H₄₆O₃Si
• 分子量: 422.724
• InChiKey: DOYUSBPBNBCUEG-GIXTYORISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.66
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (((7R,8S)-8-((E)-but-2-en-1-yl)-3-methoxy-4,7-dimethyl-4,4a,5,6,7,8-hexahydro-3H-isochromen-3-yl)oxy)-triisopropylsilane 在 叔丁基过氧化氢 、 silver hexafluoroantimonate 、 二氯[2-(4,5-二氢-2-噁唑基)喹啉]钯(II) 作用下， 以 二氯甲烷 、 水 为溶剂， 生成 4-((7R,8S)-3-methoxy-4,7-dimethyl-3-((triisopropylsilyl)oxy)-4,4a,5,6,7,8-hexahydro-3H-isochromen-8-yl)butan-2-one 、 4-((7R,8S)-3-methoxy-4,7-dimethyl-3-((triisopropylsilyl)oxy)-4,4a,5,6,7,8-hexahydro-3H-isochromen-8-yl)butan-2-one
  参考文献：
  名称：

  Wacker-Type Oxidation of Internal Alkenes using Pd(Quinox) and TBHP

  摘要：

  The Pd-catalyzed TBHP-mediated Wacker-type oxidation of internal alkenes is reported. The reaction uses 2(4,5-dihydro-2-oxazolyl)quinoline (Quinox) as ligand and TBHP(aq) as oxidant to deliver single ketone constitutional isomer products in a predictable fashion from electronically biased olefins. This methodology is showcased through its application on an advanced intermediate in the total synthesis of the antimalarial drug artemisinin.

  DOI：

  10.1021/jo302638v

文献信息

• Wacker-Type Oxidation of Internal Alkenes using Pd(Quinox) and TBHP
  作者：Ryan J. DeLuca、Jennifer L. Edwards、Laura D. Steffens、Brian W. Michel、Xiaoxiao Qiao、Chunyin Zhu、Silas P. Cook、Matthew S. Sigman

  DOI：10.1021/jo302638v

  日期：2013.2.15

  The Pd-catalyzed TBHP-mediated Wacker-type oxidation of internal alkenes is reported. The reaction uses 2(4,5-dihydro-2-oxazolyl)quinoline (Quinox) as ligand and TBHP(aq) as oxidant to deliver single ketone constitutional isomer products in a predictable fashion from electronically biased olefins. This methodology is showcased through its application on an advanced intermediate in the total synthesis of the antimalarial drug artemisinin.