6-epi-Sch 642305 | 882494-48-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 奥昔康唑
• 英文名称: 6-epi-Sch 642305
• 英文别名: (4S,8aS,12S,12aR)-12-hydroxy-4-methyl-4,5,6,7,8,8a,12,12a-octahydro-1H-3-benzoxecine-2,9-dione
• CAS: 882494-48-6
• 化学式: C₁₄H₂₀O₄
• 分子量: 252.31
• InChiKey: WTQWDNIIFGEBSZ-KQXIARHKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-epi-Sch 642305 在 三氟乙酸 作用下， 以 氘代氯仿 为溶剂， 反应 24.0h， 以65%的产率得到(S)-1,4,5,6,7,8-hexahydro-9-hydroxy-4-methyl-2H-3-benzoxecin-2-one
  参考文献：
  名称：

  Synthesis of (+)-Sch 642305 by a Biomimetic Transannular Michael Reaction

  摘要：

  The synthesis of (+)-Sch 642305 (1) has been completed in 17 steps in 1.6% overall yield. Transannular Michael reaction of 2b with NaH in THF provided cyclohexenone 23 stereospecifically. Heating 23 in TFA/CDCl3 provided a 3:1 equilibrium mixture of 23 and 25, which was hydrolyzed to give (+)-6-epi-Sch 642305 (24) and (+)-Sch 642305 (1), respectively.

  DOI：

  10.1021/ol052948+
• 作为产物：
  描述：

  (4S,8aR,12S,12aR)-12-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-4,5,6,7,8,8a,12,12a-octahydro-4-methyl-2H-3-benzoxecin-2,9(1H)-dione 在 四丁基氟化铵 、 溶剂黄146 、 三氟乙酸 作用下， 以 四氢呋喃 、 氘代氯仿 为溶剂， 反应 27.0h， 生成 6-epi-Sch 642305
  参考文献：
  名称：

  Synthesis of (+)-Sch 642305 by a Biomimetic Transannular Michael Reaction

  摘要：

  The synthesis of (+)-Sch 642305 (1) has been completed in 17 steps in 1.6% overall yield. Transannular Michael reaction of 2b with NaH in THF provided cyclohexenone 23 stereospecifically. Heating 23 in TFA/CDCl3 provided a 3:1 equilibrium mixture of 23 and 25, which was hydrolyzed to give (+)-6-epi-Sch 642305 (24) and (+)-Sch 642305 (1), respectively.

  DOI：

  10.1021/ol052948+

文献信息

• Stereoselective synthesis of Sch 642305, an inhibitor of bacterial DNA primase
  作者：Ken Ishigami、Ryo Katsuta、Hidenori Watanabe

  DOI：10.1016/j.tet.2005.12.009

  日期：2006.3

  Sch 642305 is a fungal nonanolide, which inhibits bacterial DNA primase and HIV-1 Tat transactivation. The enantioselective synthesis of Sch 642305 was succeeded starting from useful chiral building block via stereoselective dianion alkylation of beta-ketosulfoxide and lactonization. (c) 2005 Elsevier Ltd. All rights reserved.
• Synthesis of (+)-Sch 642305 by a Biomimetic Transannular Michael Reaction
  作者：Barry B. Snider、Jingye Zhou

  DOI：10.1021/ol052948+

  日期：2006.3.1

  The synthesis of (+)-Sch 642305 (1) has been completed in 17 steps in 1.6% overall yield. Transannular Michael reaction of 2b with NaH in THF provided cyclohexenone 23 stereospecifically. Heating 23 in TFA/CDCl3 provided a 3:1 equilibrium mixture of 23 and 25, which was hydrolyzed to give (+)-6-epi-Sch 642305 (24) and (+)-Sch 642305 (1), respectively.