(S)-4-{2-[(1S,2S,4S,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-2,6,6-trimethyl-bicyclo[3.1.1]hept-2-yl]-ethyl}-4-methyl-cyclohex-2-enone | 499797-37-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (S)-4-{2-[(1S,2S,4S,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-2,6,6-trimethyl-bicyclo[3.1.1]hept-2-yl]-ethyl}-4-methyl-cyclohex-2-enone
• 英文别名: (4S)-4-[2-[(1S,2S,4S,5S)-4-[tert-butyl(dimethyl)silyl]oxy-2,6,6-trimethyl-2-bicyclo[3.1.1]heptanyl]ethyl]-4-methylcyclohex-2-en-1-one
• CAS: 499797-37-4
• 化学式: C₂₅H₄₄O₂Si
• 分子量: 404.709
• InChiKey: FIGHIFMJWSCMDJ-RMWGXBEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.15
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.88
• 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)-4-{2-[(1S,2S,4S,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-2,6,6-trimethyl-bicyclo[3.1.1]hept-2-yl]-ethyl}-4-methyl-cyclohex-2-enone 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以98%的产率得到(S)-4-[2-((1S,2S,4S,5S)-4-Hydroxy-2,6,6-trimethyl-bicyclo[3.1.1]hept-2-yl)-ethyl]-4-methyl-cyclohex-2-enone
  参考文献：
  名称：

  Synthesis of the 5-7-6 Core of Guanacastepenes. Construction of C8 Quaternary Carbon via the Inversion of Stereochemistry

  摘要：

  [GRAPHICS]An efficient and unique route to the 5-7-6 core of guanacatepene A (1) is described. The installation of the desired stereochemistry at the C8 position was achieved via the desymmetrization of the cyclohexadienone by reductive ring closure of the seven-membered ring. That the closure of the seven-membered ring produced only the desired isomer is hypothesized to be a result of the more stable trans relationship between the C8 and C11 methyl groups.

  DOI：

  10.1021/ol026820t
• 作为产物：
  描述：

  马鞭草烯醇 在 tris(triphenylphosphine)ruthenium(II) chloride 、 碳酸氢钠 吡啶 、 咪唑 、 氢氧化钾 、 sodium periodate 、 四氧化锇 、 lithium aluminium tetrahydride 、 正丁基锂 、 碘 、 臭氧 、 magnesium 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 正己烷 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 丙酮 、 叔丁醇 为溶剂， 反应 504032.75h， 生成 (S)-4-{2-[(1S,2S,4S,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-2,6,6-trimethyl-bicyclo[3.1.1]hept-2-yl]-ethyl}-4-methyl-cyclohex-2-enone
  参考文献：
  名称：

  Synthesis of the 5-7-6 Core of Guanacastepenes. Construction of C8 Quaternary Carbon via the Inversion of Stereochemistry

  摘要：

  [GRAPHICS]An efficient and unique route to the 5-7-6 core of guanacatepene A (1) is described. The installation of the desired stereochemistry at the C8 position was achieved via the desymmetrization of the cyclohexadienone by reductive ring closure of the seven-membered ring. That the closure of the seven-membered ring produced only the desired isomer is hypothesized to be a result of the more stable trans relationship between the C8 and C11 methyl groups.

  DOI：

  10.1021/ol026820t

文献信息

• Synthesis of the 5-7-6 Core of Guanacastepenes. Construction of C8 Quaternary Carbon via the Inversion of Stereochemistry
  作者：Truc M. Nguyen、Robert J. Seifert、Dale R. Mowrey、Daesung Lee

  DOI：10.1021/ol026820t

  日期：2002.10.1

  [GRAPHICS]An efficient and unique route to the 5-7-6 core of guanacatepene A (1) is described. The installation of the desired stereochemistry at the C8 position was achieved via the desymmetrization of the cyclohexadienone by reductive ring closure of the seven-membered ring. That the closure of the seven-membered ring produced only the desired isomer is hypothesized to be a result of the more stable trans relationship between the C8 and C11 methyl groups.