4-methyl-1-(2-(phenylsulfonyl)ethyl)-2,6,7-trioxabicyclo[2.2.2]octane | 1394135-62-6

• 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: 4-methyl-1-(2-(phenylsulfonyl)ethyl)-2,6,7-trioxabicyclo[2.2.2]octane
• 英文别名: 4-methyl-1-(2′-(phenylsulfonyl)ethyl)-2,6,7-trioxabicyclo[2.2.2]octane；1-[2-(Benzenesulfonyl)ethyl]-4-methyl-2,6,7-trioxabicyclo[2.2.2]octane
• CAS: 1394135-62-6
• 化学式: C₁₄H₁₈O₅S
• 分子量: 298.36
• InChiKey: MPRUAMZTVHQPPK-UHFFFAOYSA-N

物化性质

• 沸点：
  441.4±38.0 °C(Predicted)
• 密度：
  1.300±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  70.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-methyl-1-(2-(phenylsulfonyl)ethyl)-2,6,7-trioxabicyclo[2.2.2]octane 、 (S)-1,2-环氧基戊烷 在 N,N-二甲基丙烯基脲 、 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.0h， 以50%的产率得到(S)-6-propyl-5,6-dihydro-2H-pyran-2-one
  参考文献：
  名称：

  Synthesis of 6,6′-Binaphthopyran-2-one Natural Products: Pigmentosin A, Talaroderxines A and B

  摘要：

  Efficient and stereoselective syntheses of pigmentosin A, talaroderxine A, and its diastereomer talaroderxine B are reported. The binaphthyl ring system is assembled by vanadium-catalyzed phenolic coupling of tricyclic precursors. These key intermediates were prepared by Michael-Dieckmann annulation of a protected orsellinate ester, with the requisite pyranones accessed by a new variant of Ghosez's sulfone-epoxide annulation. Preliminary biological experiments are reported for pigmentosin.

  DOI：

  10.1021/ol301743t
• 作为产物：
  描述：

  3-(苯磺酰)丙酸 在 potassium carbonate 、 caesium carbonate 、 间氯过氧苯甲酸 、 sodium iodide 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 52.5h， 生成 4-methyl-1-(2-(phenylsulfonyl)ethyl)-2,6,7-trioxabicyclo[2.2.2]octane
  参考文献：
  名称：

  Synthesis of 6,6′-Binaphthopyran-2-one Natural Products: Pigmentosin A, Talaroderxines A and B

  摘要：

  Efficient and stereoselective syntheses of pigmentosin A, talaroderxine A, and its diastereomer talaroderxine B are reported. The binaphthyl ring system is assembled by vanadium-catalyzed phenolic coupling of tricyclic precursors. These key intermediates were prepared by Michael-Dieckmann annulation of a protected orsellinate ester, with the requisite pyranones accessed by a new variant of Ghosez's sulfone-epoxide annulation. Preliminary biological experiments are reported for pigmentosin.

  DOI：

  10.1021/ol301743t

文献信息

• From the Total Synthesis of Semi–Viriditoxin, Semi–Viriditoxic Acid and Dimeric Naphthopyranones to their Biological Activities in Burkitt B Cell Lymphoma
  作者：Frederike Weber、Anja Weber、Laura Schmitt、Ilka Lechtenberg、Julian Greb、Birgit Henßen、Sebastian Wesselborg、Jörg Pietruszka

  DOI：10.1002/chem.202400559

  日期：——

  Various naphthopyranones were synthesized and tested for their cytotoxicity and apoptotic activity. The synthesis was carried out using two building blocks, which were prepared from enantiomerically pure oxiranes and methyl acetoacetate and then reacted with each other to form naphthopyranones. Monomeric and dimeric naphthopyranones were synthesized and then a structure–activity relationship study

  合成了各种萘并吡喃酮并测试了它们的细胞毒性和细胞凋亡活性。该合成使用两种结构单元进行，这两种结构单元由对映体纯的环氧乙烷和乙酰乙酸甲酯制备，然后彼此反应形成萘并吡喃酮。合成了单体和二聚萘并吡喃酮，然后进行了构效关系研究。
• 4-Methyl-1-(2-(phenylsulfonyl)ethyl)-2,6,7-trioxabicyclo[2.2.2]octane
  作者：Michael Maso

  DOI：10.15227/orgsyn.092.0328

  日期：——
• Synthesis of 6,6′-Binaphthopyran-2-one Natural Products: Pigmentosin A, Talaroderxines A and B
  作者：Charles I. Grove、Michael J. Di Maso、Firoz A. Jaipuri、Michelle B. Kim、Jared T. Shaw

  DOI：10.1021/ol301743t

  日期：2012.9.7

  Efficient and stereoselective syntheses of pigmentosin A, talaroderxine A, and its diastereomer talaroderxine B are reported. The binaphthyl ring system is assembled by vanadium-catalyzed phenolic coupling of tricyclic precursors. These key intermediates were prepared by Michael-Dieckmann annulation of a protected orsellinate ester, with the requisite pyranones accessed by a new variant of Ghosez's sulfone-epoxide annulation. Preliminary biological experiments are reported for pigmentosin.