3-(tert-butyldimethylsilyloxymethyl)benzofuran-5-ol | 865775-92-4

• 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: 3-(tert-butyldimethylsilyloxymethyl)benzofuran-5-ol
• 英文别名: 3-[[Tert-butyl(dimethyl)silyl]oxymethyl]-1-benzofuran-5-ol；3-[[tert-butyl(dimethyl)silyl]oxymethyl]-1-benzofuran-5-ol
• CAS: 865775-92-4
• 化学式: C₁₅H₂₂O₃Si
• 分子量: 278.423
• InChiKey: ASFJQZYMCQVDRS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.66
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  42.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(tert-butyldimethylsilyloxymethyl)benzofuran-5-ol 在 KH₂PO₄ buffer 、 potassium nitrososulfonate 、 四丁基溴化铵 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 34.0h， 生成 (+)-3(S),17-dihydroxytanshinone di-tert-butyldimethylsilyl ether
  参考文献：
  名称：

  Asymmetric synthesis of 3(S),17-dihydroxytanshinone

  摘要：

  The first synthesis of 3(S),17-dihydroxytanshinone was achieved by ultrasound promoted Diels-Alder reaction of the protected 3-hydroxymethyl-4,5-benzofurandione with a vinylcyclohexene derivative. Bioassay showed that the synthetic 3(S), 17-dihydroxytanshinone was active in vitro against HL-60 tumor cell line by MTT method. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.11.091
• 作为产物：
  描述：

  ethyl 5-hydroxybenzofuran-3-carboxylate 在 咪唑 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 46.0h， 生成 3-(tert-butyldimethylsilyloxymethyl)benzofuran-5-ol
  参考文献：
  名称：

  Asymmetric synthesis of 3(S),17-dihydroxytanshinone

  摘要：

  The first synthesis of 3(S),17-dihydroxytanshinone was achieved by ultrasound promoted Diels-Alder reaction of the protected 3-hydroxymethyl-4,5-benzofurandione with a vinylcyclohexene derivative. Bioassay showed that the synthetic 3(S), 17-dihydroxytanshinone was active in vitro against HL-60 tumor cell line by MTT method. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.11.091

文献信息

• Asymmetric synthesis of 3(S),17-dihydroxytanshinone
  作者：Jiangang Zhang、Wenhu Duan、Junchao Cai

  DOI：10.1016/j.tet.2003.11.091

  日期：2004.2

  The first synthesis of 3(S),17-dihydroxytanshinone was achieved by ultrasound promoted Diels-Alder reaction of the protected 3-hydroxymethyl-4,5-benzofurandione with a vinylcyclohexene derivative. Bioassay showed that the synthetic 3(S), 17-dihydroxytanshinone was active in vitro against HL-60 tumor cell line by MTT method. (C) 2003 Elsevier Ltd. All rights reserved.