3,3-dimethyl-2,3-dihydro-1H-benzo[f]chromen-8-ol | 858032-15-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: 3,3-dimethyl-2,3-dihydro-1H-benzo[f]chromen-8-ol
• 英文别名: 3,3-dimethyl-1,2-dihydrobenzo[f]chromen-8-ol
• CAS: 858032-15-2
• 化学式: C₁₅H₁₆O₂
• 分子量: 228.291
• InChiKey: NRRZIWAWAOFFFG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-(3-methylbut-2-en-1-yl)naphthalene-2,6-diol 、 1,5-bis(3-methylbut-2-en-1-yl)naphthalene-2,6-diol 在 iron(III) chloride 作用下， 以 异丙醇 为溶剂， 反应 3.0h， 以30%的产率得到3,3-dimethyl-2,3-dihydro-1H-benzo[f]chromen-8-ol
  参考文献：
  名称：

  Chromane derivatives of small aromatic molecules: Chemoenzymatic synthesis and growth inhibitory activity on human tumor cell line LoVo WT

  摘要：

  Aromatic substrates tyrosol (p-hydroxyphenylethanol) and 2,6-dihydroxynaphthalene (2,6-DHN) were converted into chromane derivatives by means of chemoenzymatic reactions catalyzed by the aromatic prenyltransferase of bacterial origin NovQ, using dimethylallyl bromide as allylic substrate instead of the natural isoprenyl pyrophosphate substrate. Stereoselective prenylation occurred in o-position with respect to the phenol hydroxyl in both compounds. Prenylated derivatives were readily converted into chromane products via a selective 6-endo-trig cyclization involving the oxygen atom from the phenol moiety and the double bond of the prenyl substituent, a process catalyzed by FeCl3. These findings set up the basis of a most convenient two-step, one-pot process which allows for easy recovery of the chromane products in high yields. The chromane derivatives thus obtained were tested for cytotoxicity and pro-apoptotic activity using LoVo WT cells, a line of human colon adenocarcinoma. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.06.061

文献信息

• Chromane derivatives of small aromatic molecules: Chemoenzymatic synthesis and growth inhibitory activity on human tumor cell line LoVo WT
  作者：Alberto Macone、Eugenio Lendaro、Alessandra Comandini、Irene Rovardi、Rosa Marina Matarese、Antonio Carraturo、Alessandra Bonamore

  DOI：10.1016/j.bmc.2009.06.061

  日期：2009.8

  Aromatic substrates tyrosol (p-hydroxyphenylethanol) and 2,6-dihydroxynaphthalene (2,6-DHN) were converted into chromane derivatives by means of chemoenzymatic reactions catalyzed by the aromatic prenyltransferase of bacterial origin NovQ, using dimethylallyl bromide as allylic substrate instead of the natural isoprenyl pyrophosphate substrate. Stereoselective prenylation occurred in o-position with respect to the phenol hydroxyl in both compounds. Prenylated derivatives were readily converted into chromane products via a selective 6-endo-trig cyclization involving the oxygen atom from the phenol moiety and the double bond of the prenyl substituent, a process catalyzed by FeCl3. These findings set up the basis of a most convenient two-step, one-pot process which allows for easy recovery of the chromane products in high yields. The chromane derivatives thus obtained were tested for cytotoxicity and pro-apoptotic activity using LoVo WT cells, a line of human colon adenocarcinoma. (C) 2009 Elsevier Ltd. All rights reserved.