(2E)-3-(8-{[tert-butyl(dimethyl)silyl]oxy}-1,2,3,4-tetrahydrodibenzo[b,d]furan-1-yl)-2-methylacrylaldehyde | 1246172-12-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: (2E)-3-(8-{[tert-butyl(dimethyl)silyl]oxy}-1,2,3,4-tetrahydrodibenzo[b,d]furan-1-yl)-2-methylacrylaldehyde
• 英文别名: (E)-3-[8-[tert-butyl(dimethyl)silyl]oxy-1,2,3,4-tetrahydrodibenzofuran-1-yl]-2-methylprop-2-enal
• CAS: 1246172-12-2
• 化学式: C₂₂H₃₀O₃Si
• 分子量: 370.564
• InChiKey: VREQBMIJPWSCAD-NTCAYCPXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.38
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  39.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2E)-3-(8-{[tert-butyl(dimethyl)silyl]oxy}-1,2,3,4-tetrahydrodibenzo[b,d]furan-1-yl)-2-methylacrylaldehyde 在 manganese(IV) oxide 、 锂硼氢 、 18-冠醚-6 、 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 methyl (2E,4Z,6E)-7-(8-{[tert-butyl(dimethyl)silyl]oxy}-1,2,3,4-tetrahydrodibenzo[b,d]furan-1-yl)-4-methoxy-6-methylhepta-2,4,6-trienoate
  参考文献：
  名称：

  Total synthesis and structural confirmation of (±)-cuevaene A

  摘要：

  The total synthesis and structural reassignment of cuevaene A have been completed. The key synthetic steps in the total synthesis included a base-promoted double conjugate addition and further elaboration to generate the tricyclic core structure, followed by construction of the trienoic acid side chain. Detailed comparison of proton and carbon NMR data with published values enabled the connectivity of the natural product, which had been debated in earlier publications, to be confirmed. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.07.121
• 作为产物：
  描述：

  1,4-二氧杂螺[4.5]癸-6,9-二烯-8-酮 在 咪唑 、 盐酸 、 manganese(IV) oxide 、 硼烷四氢呋喃络合物 、 草酰氯 、 potassium tert-butylate 、 trimethylsilylmethyllithium 、 二异丁基氢化铝 、 二甲基亚砜 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 正己烷 、 二氯甲烷 、 水 、 甲苯 、 正戊烷 、 正丁醇 为溶剂， 反应 162.5h， 生成 (2E)-3-(8-{[tert-butyl(dimethyl)silyl]oxy}-1,2,3,4-tetrahydrodibenzo[b,d]furan-1-yl)-2-methylacrylaldehyde
  参考文献：
  名称：

  Total synthesis and structural confirmation of (±)-cuevaene A

  摘要：

  The total synthesis and structural reassignment of cuevaene A have been completed. The key synthetic steps in the total synthesis included a base-promoted double conjugate addition and further elaboration to generate the tricyclic core structure, followed by construction of the trienoic acid side chain. Detailed comparison of proton and carbon NMR data with published values enabled the connectivity of the natural product, which had been debated in earlier publications, to be confirmed. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.07.121

文献信息

• Total syntheses of the proposed structures of cuevaene A
  作者：Yunxiu Chen、Jianfeng Huang、Bo Liu

  DOI：10.1016/j.tetlet.2010.06.133

  日期：2010.9

  Two proposed structures of cuevaene A were synthesized and the NMR spectra of both structures are proved to be inconsistent with those of the natural product. The structure of cuevaene A is still unclear and needs to be revised. (C) 2010 Elsevier Ltd. All rights reserved.