tert-Butyl-{(1S,2S,4S,5S)-4-[2-((R)-1,3-dimethyl-cyclopent-2-enyl)-ethyl]-4,6,6-trimethyl-bicyclo[3.1.1]hept-2-yloxy}-dimethyl-silane | 499797-36-3

• 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: tert-Butyl-{(1S,2S,4S,5S)-4-[2-((R)-1,3-dimethyl-cyclopent-2-enyl)-ethyl]-4,6,6-trimethyl-bicyclo[3.1.1]hept-2-yloxy}-dimethyl-silane
• 英文别名: tert-butyl-[[(1S,2S,4S,5S)-4-[2-[(1R)-1,3-dimethylcyclopent-2-en-1-yl]ethyl]-4,6,6-trimethyl-2-bicyclo[3.1.1]heptanyl]oxy]-dimethylsilane
• CAS: 499797-36-3
• 化学式: C₂₅H₄₆OSi
• 分子量: 390.725
• InChiKey: QJPABVCJADYKEC-RMWGXBEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.98
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  tert-Butyl-{(1S,2S,4S,5S)-4-[2-((R)-1,3-dimethyl-cyclopent-2-enyl)-ethyl]-4,6,6-trimethyl-bicyclo[3.1.1]hept-2-yloxy}-dimethyl-silane 在 碳酸氢钠 吡啶 、 氢氧化钾 、 sodium periodate 、 四氧化锇 、 四丁基氟化铵 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 甲醇 、 水 、 叔丁醇 为溶剂， 反应 504033.0h， 生成 (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 咪唑 、 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 、 乙醚 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 23.75h， 生成 tert-Butyl-{(1S,2S,4S,5S)-4-[2-((R)-1,3-dimethyl-cyclopent-2-enyl)-ethyl]-4,6,6-trimethyl-bicyclo[3.1.1]hept-2-yloxy}-dimethyl-silane
  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.