6-(tert-butyldimethylsilyloxy)-2-(1-methyl-3-trimethylsilylprop-2-yn-1-yl)indan-1-one | 930278-45-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 6-(tert-butyldimethylsilyloxy)-2-(1-methyl-3-trimethylsilylprop-2-yn-1-yl)indan-1-one
• 英文别名: 6-[Tert-butyl(dimethyl)silyl]oxy-2-(4-trimethylsilylbut-3-yn-2-yl)-2,3-dihydroinden-1-one
• CAS: 930278-45-8
• 化学式: C₂₂H₃₄O₂Si₂
• 分子量: 386.682
• InChiKey: QFAAZLRLPYQSKZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.94
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 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：

  6-(tert-butyldimethylsilyloxy)-2-(1-methyl-3-trimethylsilylprop-2-yn-1-yl)indan-1-one 在 咪唑 、 sodium tetrahydroborate 、 四丁基氟化铵 、 甲基锂 、 叔丁基锂 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 正戊烷 为溶剂， 反应 10.17h， 生成 (6SR,7SR)-11-(tert-butyldimethylsilyloxy)-4,4,7-trimethyl-1,2,3,4,5,6,7,8-octahydrodibenzo[a,h]azulen-6(2H)-ol
  参考文献：
  名称：

  Total syntheses of (±)-frondosin C and (±)-8-epi-frondosin C via a tandem anionic 5-exo dig cyclization–Claisen rearrangement sequence

  摘要：

  Microwave-assisted anionic 5-exo dig cyclization-Claisen rearrangement sequence has been investigated as a convenient 'one-pot' route to fused cycloheptanoid ring systems. This process was used as the key transformation to construct the tetracyclic framework of frondosin C. Subsequent manipulation of the core allowed the first total syntheses of (+/-)-frondosin C and (+/-)-8-epi-frondosin C in a combined overall yield of 20.8% over 14 steps. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.12.057
• 作为产物：
  描述：

  6-羟基-1-茚酮 在 咪唑 、 草酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.5h， 生成 6-(tert-butyldimethylsilyloxy)-2-(1-methyl-3-trimethylsilylprop-2-yn-1-yl)indan-1-one
  参考文献：
  名称：

  Total syntheses of (±)-frondosin C and (±)-8-epi-frondosin C via a tandem anionic 5-exo dig cyclization–Claisen rearrangement sequence

  摘要：

  Microwave-assisted anionic 5-exo dig cyclization-Claisen rearrangement sequence has been investigated as a convenient 'one-pot' route to fused cycloheptanoid ring systems. This process was used as the key transformation to construct the tetracyclic framework of frondosin C. Subsequent manipulation of the core allowed the first total syntheses of (+/-)-frondosin C and (+/-)-8-epi-frondosin C in a combined overall yield of 20.8% over 14 steps. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.12.057

文献信息

• Total syntheses of (±)-frondosin C and (±)-8-epi-frondosin C via a tandem anionic 5-exo dig cyclization–Claisen rearrangement sequence
  作者：Xin Li、Robert E. Kyne、Timo V. Ovaska

  DOI：10.1016/j.tet.2006.12.057

  日期：2007.2

  Microwave-assisted anionic 5-exo dig cyclization-Claisen rearrangement sequence has been investigated as a convenient 'one-pot' route to fused cycloheptanoid ring systems. This process was used as the key transformation to construct the tetracyclic framework of frondosin C. Subsequent manipulation of the core allowed the first total syntheses of (+/-)-frondosin C and (+/-)-8-epi-frondosin C in a combined overall yield of 20.8% over 14 steps. (c) 2006 Elsevier Ltd. All rights reserved.