(3E,5S,6Z,14S)-5-[(1,1-dimethylethyl)diphenylsilyloxy]-14-methyloxacyclotetradeca-3,6-diene-2,8-dione | 884869-15-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酯类和类似物
• 英文名称: (3E,5S,6Z,14S)-5-[(1,1-dimethylethyl)diphenylsilyloxy]-14-methyloxacyclotetradeca-3,6-diene-2,8-dione
• 英文别名: (3E,5S,6Z,14S)-5-[tert-butyl(diphenyl)silyl]oxy-14-methyl-1-oxacyclotetradeca-3,6-diene-2,8-dione
• CAS: 884869-15-2
• 化学式: C₃₀H₃₈O₄Si
• 分子量: 490.715
• InChiKey: IAJCSPSDQLFRGN-OKQKPEGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.51
• 重原子数：
  35
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3E,5S,6Z,14S)-5-[(1,1-dimethylethyl)diphenylsilyloxy]-14-methyloxacyclotetradeca-3,6-diene-2,8-dione 在 sodium hydride 、 三氟乙酸 作用下， 以 四氢呋喃 、 氘代氯仿 为溶剂， 120.0 ℃ 、20.68 kPa 条件下， 反应 3.5h， 生成 (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
  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：

  (6Z,8RS,9E,13S)-8-[(1,1-dimethylethyl)diphenylsilyloxy]-13-methyl-1,4,12-trioxaspiro[4.13]octadeca-6,9-dien-11-one 在 对甲苯磺酸 作用下， 以 水 、 丙酮 为溶剂， 反应 16.0h， 以43%的产率得到(3E,5S,6Z,14S)-5-[(1,1-dimethylethyl)diphenylsilyloxy]-14-methyloxacyclotetradeca-3,6-diene-2,8-dione
  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

• 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.