tert-butyl-[[(5R,8S)-4-[tert-butyl(dimethyl)silyl]oxy-2-methoxy-3,8-dimethyl-5-[(2S)-6-methylhept-5-en-2-yl]-5,6,7,8-tetrahydronaphthalen-1-yl]oxy]-dimethylsilane | 934501-00-5

• 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-[[(5R,8S)-4-[tert-butyl(dimethyl)silyl]oxy-2-methoxy-3,8-dimethyl-5-[(2S)-6-methylhept-5-en-2-yl]-5,6,7,8-tetrahydronaphthalen-1-yl]oxy]-dimethylsilane
• CAS: 934501-00-5
• 化学式: C₃₃H₆₀O₃Si₂
• 分子量: 561.009
• InChiKey: JBRVRSTYWSIFOA-KYPHJKQUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.14
• 重原子数：
  38
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl-[[(5R,8S)-4-[tert-butyl(dimethyl)silyl]oxy-2-methoxy-3,8-dimethyl-5-[(2S)-6-methylhept-5-en-2-yl]-5,6,7,8-tetrahydronaphthalen-1-yl]oxy]-dimethylsilane 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 以65%的产率得到O-methyl-elisabethadione
  参考文献：
  名称：

  Synthetic and Isolation Studies Related to the Marine Natural Products (+)-Elisabethadione and (+)-Elisabethamine

  摘要：

  These studies were conducted to determine the discrepancies between the spectroscopic data of the isolated and synthetic samples of the marine natural product (+)-elisabethadione. Attempts at the re-isolation of (+)-elisabethadione from Pseudopterogorgia elisabethae were unsuccessful, but during these efforts, two related natural products of O-methylelisabethadione (8) and O-methyl-nor-elisabethadione (9) were discovered. The total syntheses of these new natural products were accomplished by using the combined C-H activation/Cope rearrangement as the key step and the previously synthesized elisabethadione was converted to O-methylelisabethadione. These studies confirmed that the synthetic sample of (+)-elisabthadione was assigned the correct structure. The considerable differences in the data between the synthetic and natural samples of (+)-elisabethadione lead to the conclusion that the structure of the natural material was either miss-assigned or the published spectral data were incorrect. During the course of these studies, questions arose about the assigned structure of another natural product, elisabethamine, which was proposed to be an aminohydroquinone. Attempts at the synthesis of this compound revealed that the aminohydroquinone structure was unstable in air as it was readily oxidized to the quinone.

  DOI：

  10.1021/jo0618167
• 作为产物：
  描述：

  (S)-4-[(1R,4S)-5,8-Bis-(tert-butyl-dimethyl-silanyloxy)-6-methoxy-4,7-dimethyl-1,2,3,4-tetrahydro-naphthalen-1-yl]-pentanal 、 碘化异丙基三苯鏻 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以77%的产率得到tert-butyl-[[(5R,8S)-4-[tert-butyl(dimethyl)silyl]oxy-2-methoxy-3,8-dimethyl-5-[(2S)-6-methylhept-5-en-2-yl]-5,6,7,8-tetrahydronaphthalen-1-yl]oxy]-dimethylsilane
  参考文献：
  名称：

  Synthetic and Isolation Studies Related to the Marine Natural Products (+)-Elisabethadione and (+)-Elisabethamine

  摘要：

  These studies were conducted to determine the discrepancies between the spectroscopic data of the isolated and synthetic samples of the marine natural product (+)-elisabethadione. Attempts at the re-isolation of (+)-elisabethadione from Pseudopterogorgia elisabethae were unsuccessful, but during these efforts, two related natural products of O-methylelisabethadione (8) and O-methyl-nor-elisabethadione (9) were discovered. The total syntheses of these new natural products were accomplished by using the combined C-H activation/Cope rearrangement as the key step and the previously synthesized elisabethadione was converted to O-methylelisabethadione. These studies confirmed that the synthetic sample of (+)-elisabthadione was assigned the correct structure. The considerable differences in the data between the synthetic and natural samples of (+)-elisabethadione lead to the conclusion that the structure of the natural material was either miss-assigned or the published spectral data were incorrect. During the course of these studies, questions arose about the assigned structure of another natural product, elisabethamine, which was proposed to be an aminohydroquinone. Attempts at the synthesis of this compound revealed that the aminohydroquinone structure was unstable in air as it was readily oxidized to the quinone.

  DOI：

  10.1021/jo0618167

文献信息

• Synthetic and Isolation Studies Related to the Marine Natural Products (+)-Elisabethadione and (+)-Elisabethamine
  作者：Xing Dai、Zhongliang Wan、Russell G. Kerr、Huw M. L. Davies

  DOI：10.1021/jo0618167

  日期：2007.3.1

  These studies were conducted to determine the discrepancies between the spectroscopic data of the isolated and synthetic samples of the marine natural product (+)-elisabethadione. Attempts at the re-isolation of (+)-elisabethadione from Pseudopterogorgia elisabethae were unsuccessful, but during these efforts, two related natural products of O-methylelisabethadione (8) and O-methyl-nor-elisabethadione (9) were discovered. The total syntheses of these new natural products were accomplished by using the combined C-H activation/Cope rearrangement as the key step and the previously synthesized elisabethadione was converted to O-methylelisabethadione. These studies confirmed that the synthetic sample of (+)-elisabthadione was assigned the correct structure. The considerable differences in the data between the synthetic and natural samples of (+)-elisabethadione lead to the conclusion that the structure of the natural material was either miss-assigned or the published spectral data were incorrect. During the course of these studies, questions arose about the assigned structure of another natural product, elisabethamine, which was proposed to be an aminohydroquinone. Attempts at the synthesis of this compound revealed that the aminohydroquinone structure was unstable in air as it was readily oxidized to the quinone.