<1SR,3aSR,4SR,8aSR>-1-(t-Butyldimethylsiloxy)-4,8a-dimethyl-octahydro-6(1H)-azulenon

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: <1SR,3aSR,4SR,8aSR>-1-(t-Butyldimethylsiloxy)-4,8a-dimethyl-octahydro-6(1H)-azulenon
• 英文别名: (1S,3aS,4S,8aS)-1-[tert-butyl(dimethyl)silyl]oxy-4,8a-dimethyl-1,2,3,3a,4,5,7,8-octahydroazulen-6-one
• 化学式: C₁₈H₃₄O₂Si
• 分子量: 310.552
• InChiKey: UCYOSFBXGOWWQS-MBGYTDRXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.18
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.94
• 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：

  <1SR,3aSR,4SR,8aSR>-1-(t-Butyldimethylsiloxy)-4,8a-dimethyl-octahydro-6(1H)-azulenon 在 氢氟酸 作用下， 以 乙腈 为溶剂， 生成 (1SR,2SR,7SR,8SR)-2,7-dimethyl-8-hydroxybicyclo<5.3.0>decan-4-one
  参考文献：
  名称：

  Boron annulation in organic synthesis. 2. confertin & helenalin

  摘要：

  DOI：

  10.1016/s0040-4039(00)80138-0
• 作为产物：
  描述：

  tert-butyl-[(1S,2S,3S)-2-ethenyl-2-methyl-3-prop-1-en-2-ylcyclopentyl]oxy-dimethylsilane 生成 <1SR,3aSR,4SR,8aSR>-1-(t-Butyldimethylsiloxy)-4,8a-dimethyl-octahydro-6(1H)-azulenon
  参考文献：
  名称：

  WELCH, MICHAEL C.;BRYSON, THOMAS A., TETRAHEDRON LETT., 29,(1988) N 5, 521-524

  摘要：

  DOI：

文献信息

• A new route to functionalised hydroazulenes. Synthesis of (±)-confertin
  作者：Michael Kennedy、M. Anthony McKervey

  DOI：10.1039/c39880001028

  日期：——

  The advanced confertin intermediate (13) has been synthesised in 20% yield from a simple dihydrocinnamic acid precursor, the hydroazulene skeleton having been constructed by rhodium(II) mandelate-catalysed cyclisation–ring expansion of an α-diazoketone.

  先进的confertin中间体（13）是由一种简单的二氢肉桂酸前体合成的，产率为20％，该水解腈骨架是由扁桃酸铑（II）催化的α-二氮酮的环化-扩环构建的。
• Pseudoguaianolides from intramolecular cycloadditions of aryl diazoketones: synthesis of (±)-confertin and an approach to the synthesis of (±)-damsin
  作者：Michael Kennedy、M. Anthony McKervey

  DOI：10.1039/p19910002565

  日期：——

  Rhodium(II) mandelate-catalysed cyclisation of alpha-diazoketones derived from 3-arylpropionic acids produces bicyclo[5.3.0]decatrienones, one of which has been used to synthesise an advanced (+/-)-confertin intermediate in six stages and 20% overall yield. The possibility of constructing intermediates for the synthesis of damsin-like pseudoguaianolides via catalysed diazoketone cyclisation is also examined and methods for the construction of polyfunctional 3-arylpropionic acids suitable for use as damsin precursors are presented.
• Quinkert, Gerhard; Schmalz, Hans-Guenther; Walzer, Egon, Angewandte Chemie, 1987, vol. 99, # 1, p. 82 - 84
  作者：Quinkert, Gerhard、Schmalz, Hans-Guenther、Walzer, Egon、Kowalczyk-Przewloka, Teresa、Duerner, Gerd、Bats, Jan W.

  DOI：——

  日期：——
• Enantioselective Conjugate Addition Greatly Improves the Synthesis of (+)-Confertin
  作者：Gerhard Quinkert、Thomas Müller、Andreas Königer、Oliver Schultheis、Birgitt Sickenberger、Gerd Dürner

  DOI：10.1016/s0040-4039(00)92665-0

  日期：1992.6

  The five-membered ring building blocks 2+3 are enantioselectively produced by conjugate addition of a chiral ligand-modified organocuprate to 2-methylcyclopent-2-enone (1) (chemical yield: 88%; e.e.: 88%) and successfully converted in a multi-step sequence, after final enantioselection by recrystallization of an appropriate intermediate, into the pseudoguaianolide (+)-confertin (5).
• Novel and general entry into pseudoguaianolides. Formal and enantioselective synthesis of (+)-confertin
  作者：Masafumi Ohtsuka、Yuki Takekawa、Kozo Shishido

  DOI：10.1016/s0040-4039(98)01180-0

  日期：1998.8

  A novel and general access to pseudoguaianolide sesquiterpenoids has been developed by employing a diastereoselective acyl radical-mediated 7-endo-trigonal mode of cyclization as a key reaction step. The methodology has successfully been applied to the formal enantioselective synthesis of (+)-confertin. (C) 1998 Elsevier Science Ltd. All rights reserved.