(1S,7aS)-7,7a-dihydro-7a-methyl-1-<<2-(trimethylsilyl)ethoxy>methoxy>-5(6H)-indanone | 102650-61-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,7aS)-7,7a-dihydro-7a-methyl-1-<<2-(trimethylsilyl)ethoxy>methoxy>-5(6H)-indanone
• 英文别名: (1S,7aS)-7,7a-dihydro-7a-methyl-1-{[2-(trimethylsilyl)ethoxy]methoxy}-5(6H)-indanone；(1S,7AS)-7A-Methyl-1-{[2-(trimethylsilyl)ethoxy]methoxy}-1,2,3,6,7,7A-hexahydro-5H-inden-5-one；(1S,7aS)-7a-methyl-1-(2-trimethylsilylethoxymethoxy)-2,3,6,7-tetrahydro-1H-inden-5-one
• CAS: 102650-61-3
• 化学式: C₁₆H₂₈O₃Si
• 分子量: 296.482
• InChiKey: ROKOVAGLCOZGRV-HOTGVXAUSA-N

物化性质

• 沸点：
  370.6±42.0 °C(Predicted)
• 密度：
  1.00±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.77
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1S,7aS)-7,7a-dihydro-7a-methyl-1-<<2-(trimethylsilyl)ethoxy>methoxy>-5(6H)-indanone 在 双氧水 、 乙酸酐 、 lithium diisopropyl amide 作用下， 以 乙醚 、 水 、 乙酸乙酯 为溶剂， 反应 7.75h， 生成 Acetic acid 3-(5-hydroxy-2-methyl-phenyl)-1-(2-trimethylsilanyl-ethoxymethoxy)-propyl ester
  参考文献：
  名称：

  Synthesis and photochemical rearrangements of bicyclic cross-conjugated cyclohexadienones containing .delta.-oxy substituents

  摘要：

  Several 6/5-fused cross-conjugated cyclohexadienones containing delta-oxy substituents on the B ring including the benzoyl, SEM, and TBDPS hydroxyl-protected systems 12b, 12f, and 12g were prepared from the corresponding enones by the phenylselenenylation-selenoxide elimination procedure. Attempted preparation of dienones 12a, 12c, and 12d containing tert-butyl, methyl, and trimethylsilyl hydroxyl-protecting groups failed. Instead, the phenolic aldehyde 13 was obtained after workup or column chromatography on silica gel. The THP-protected dienone 12e could be purified and characterized, but it gave aldehyde 13 on standing in acetic acid at room temperature. Irradiations of dienones 12b, 12f, and 12g in glacial acetic acid using a high-pressure mercury lamp housed in a Pyrex probe gave mixtures containing several photoproducts. The corresponding 5/6-fused acetoxy ketones 22a, 22c, and 22b were the major products in each case. The 5/6-fused hydroxy ketone 23 was also obtained from dienone 22a. Mixtures of tricyclic ketones of the type 27 and 28 resulting from rare examples of trapping of Zimmerman-Schuster cyclopropyl carbocation intermediates, i.e., 26, by the solvent were also obtained from all three dienones. Dienones 12g and 12f also gave tricyclic acetoxy ketones 31a and 31b, which presumably arose via a 1,4-sigmatropic rearrangement of an excited-state precursor of 26.

  DOI：

  10.1021/jo00022a018
• 作为产物：
  描述：

  (S)-(+)-2,3,7,7A-四氢-7A-甲基-1H-茚-1,5(6H)-二酮 在 lithium tri(t-butoxy)aluminum hydride 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 (1S,7aS)-7,7a-dihydro-7a-methyl-1-<<2-(trimethylsilyl)ethoxy>methoxy>-5(6H)-indanone
  参考文献：
  名称：

  Enantiospecific total synthesis of the sesquiterpene antibiotics (-)-punctatin A and (+)-punctatin D

  摘要：

  DOI：

  10.1021/ja00244a025

文献信息

• Enantiospecific total synthesis and absolute configurational assignment of (-)-punctatin A (antibiotic M95464)
  作者：Leo A. Paquette、Takashi. Sugimura

  DOI：10.1021/ja00273a056

  日期：1986.6
• Tietze, Lutz F.; Beifuss, Uwe; Loekoes, Magdolna, Angewandte Chemie, 1990, vol. 102, # 5, p. 545 - 547
  作者：Tietze, Lutz F.、Beifuss, Uwe、Loekoes, Magdolna、Rischer, Matthias、Goehrt, Axel、Sheldrick, George M.

  DOI：——

  日期：——
• TIETZE, LUTZ F.;BEIFUSS. , UWE;LOKOS, MAGDOLNA;RISCHER, MATTHIAS;GOHRT, A+, ANGEW. CHEM., 102,(1990) N, C. 545-547
  作者：TIETZE, LUTZ F.、BEIFUSS. , UWE、LOKOS, MAGDOLNA、RISCHER, MATTHIAS、GOHRT, A+

  DOI：——

  日期：——