6-[3-[Tert-butyl(dimethyl)silyl]oxypentyl]-4-hydroxy-6-methylcyclohex-2-en-1-one | 1268157-13-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-[3-[Tert-butyl(dimethyl)silyl]oxypentyl]-4-hydroxy-6-methylcyclohex-2-en-1-one
• CAS: 1268157-13-6
• 化学式: C₁₈H₃₄O₃Si
• 分子量: 326.552
• InChiKey: FQSGAKAJWCDYPU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.46
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-[3-[Tert-butyl(dimethyl)silyl]oxypentyl]-4-hydroxy-6-methylcyclohex-2-en-1-one 在 氢氟酸 、 戴斯-马丁氧化剂 、 对甲苯磺酸 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 生成 rac-3-oxodiplophyllin
  参考文献：
  名称：

  Synthesis of yomogin using a telescoped α-methylene-γ-butyrolactone annelation procedure

  摘要：

  A novel and efficient synthetic route to the anti-cancer natural product yomogin has been developed using a Telescoped Intramolecular Michael-Olefination (TIMO) sequence as the key step. Two variants of the TIMO sequence have been used successfully: a two-step acylation approach using diethyl phosphonoacetic acid and a base-free variant using triphenylphosphoranylideneketene (Bestmann's ylide). The natural product, 3-oxodiplophyllin, was also prepared en route to yomogin. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.11.143
• 作为产物：
  描述：

  在 草酸 作用下， 以 甲醇 为溶剂， 生成 6-[3-[Tert-butyl(dimethyl)silyl]oxypentyl]-4-hydroxy-6-methylcyclohex-2-en-1-one
  参考文献：
  名称：

  Synthesis of yomogin using a telescoped α-methylene-γ-butyrolactone annelation procedure

  摘要：

  A novel and efficient synthetic route to the anti-cancer natural product yomogin has been developed using a Telescoped Intramolecular Michael-Olefination (TIMO) sequence as the key step. Two variants of the TIMO sequence have been used successfully: a two-step acylation approach using diethyl phosphonoacetic acid and a base-free variant using triphenylphosphoranylideneketene (Bestmann's ylide). The natural product, 3-oxodiplophyllin, was also prepared en route to yomogin. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.11.143

文献信息

• Synthesis of yomogin using a telescoped α-methylene-γ-butyrolactone annelation procedure
  作者：Russell R.A. Kitson、Graeme D. McAllister、Richard J.K. Taylor

  DOI：10.1016/j.tetlet.2010.11.143

  日期：2011.2

  A novel and efficient synthetic route to the anti-cancer natural product yomogin has been developed using a Telescoped Intramolecular Michael-Olefination (TIMO) sequence as the key step. Two variants of the TIMO sequence have been used successfully: a two-step acylation approach using diethyl phosphonoacetic acid and a base-free variant using triphenylphosphoranylideneketene (Bestmann's ylide). The natural product, 3-oxodiplophyllin, was also prepared en route to yomogin. (C) 2010 Elsevier Ltd. All rights reserved.