(S)-2-allyl-4-(tert-butyldimethylsilyloxy)cyclohex-2-enone | 1005488-10-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-2-allyl-4-(tert-butyldimethylsilyloxy)cyclohex-2-enone
• 英文别名: (4S)-4-[tert-butyl(dimethyl)silyl]oxy-2-prop-2-enylcyclohex-2-en-1-one
• CAS: 1005488-10-7
• 化学式: C₁₅H₂₆O₂Si
• 分子量: 266.456
• InChiKey: SHMMBOARLFMUKZ-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.24
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-2-allyl-4-(tert-butyldimethylsilyloxy)cyclohex-2-enone 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 生成 (S)-2-allyl-4-hydroxycyclohex-2-enone
  参考文献：
  名称：

  A Convergent Synthesis of the Tricyclic Core of the Dictyosphaeric Acids

  摘要：

  The first synthetic route to the tricyclic core of the dictyosphaeric acids has been established starting from readily available (S)-(-)-4-(tert-butyldimethylsilyloxy)cyclohexenone and involving 9 steps, including a ring-closing metathesis to produce a 13-membered macrolactone, and a doubly tethered intramolecular Michael addition.

  DOI：

  10.1021/ol702887e
• 作为产物：
  描述：

  烯丙基三丁基锡 、 (4S)-4-[(tert-Butyldimethylsilyl)oxy]-2-iodocyclohex-2-en-1-one 在 四(三苯基膦)钯 作用下， 以 四氢呋喃 为溶剂， 反应 17.0h， 以83%的产率得到(S)-2-allyl-4-(tert-butyldimethylsilyloxy)cyclohex-2-enone
  参考文献：
  名称：

  A Convergent Synthesis of the Tricyclic Core of the Dictyosphaeric Acids

  摘要：

  The first synthetic route to the tricyclic core of the dictyosphaeric acids has been established starting from readily available (S)-(-)-4-(tert-butyldimethylsilyloxy)cyclohexenone and involving 9 steps, including a ring-closing metathesis to produce a 13-membered macrolactone, and a doubly tethered intramolecular Michael addition.

  DOI：

  10.1021/ol702887e

文献信息

• A Convergent Synthesis of the Tricyclic Core of the Dictyosphaeric Acids
  作者：Christopher W. Barfoot、Alan R. Burns、Michael G. Edwards、Martin N. Kenworthy、Mahmood Ahmed、Stephen E. Shanahan、Richard J. K. Taylor

  DOI：10.1021/ol702887e

  日期：2008.1.1

  The first synthetic route to the tricyclic core of the dictyosphaeric acids has been established starting from readily available (S)-(-)-4-(tert-butyldimethylsilyloxy)cyclohexenone and involving 9 steps, including a ring-closing metathesis to produce a 13-membered macrolactone, and a doubly tethered intramolecular Michael addition.