2-(3-methoxybenzyl)-3-furoic acid | 55888-93-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 英文名称: 2-(3-methoxybenzyl)-3-furoic acid
• 英文别名: 2-[(3-Methoxyphenyl)methyl]furan-3-carboxylic acid
• CAS: 55888-93-2
• 化学式: C₁₃H₁₂O₄
• 分子量: 232.236
• InChiKey: YEGOOIPLWUUVTG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  59.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(3-methoxybenzyl)-3-furoic acid 在 三氯化铝 、 salcomine 、 氧气 、 magnesium sulfate 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 25.67h， 生成 9-Methoxy-14-(2,2,5-trimethyl-1,3-dioxan-5-yl)-3-oxa-14-azatetracyclo[6.6.1.02,6.012,15]pentadeca-1(15),2(6),4,8,10,12-hexaen-7-one
  参考文献：
  名称：

  Synthesis of Furanonaphthoquinones with Hydroxyamino Side Chains

  摘要：

  Several furanonaphthoquinones have shown useful activity in a yeast assay for DNA-damaging agents and cytotoxicity in mammalian cell culture assays. These results, together with the planar aromatic character of the furanonaphthoquinones, suggested that they might be acting as DNA intercalators. In an attempt to improve this activity, various analogues containing a hydroxyamino side chain have been synthesized. The analogues were prepared by standard methods, but some unexpected reactions were observed nonetheless. Thus, 8-formyl-5-methoxy-4,9-dihydronaphtho[2,3-b]furan-4,9-dione (24) showed an unusual reactivity toward reductive amination, with the reaction proceeding further to give one of two different cyclized products, depending on the amination reagent used. Bioassay results indicated that only simple furanonaphthoquines showed activity in a yeast assay for DNA-damaging agents; compounds with a substituted hydroxyamino side chain were uniformly inactive in this assay. Most of the compounds with a substituted hydroxyamino side chain on the furan ring did, however, show cytotoxicity, although none of them was any more active than the simple aldehyde 2-formyl-4,9-dihydronaphtho[2,3-b]furan-4,9-dione (14). This evidence tends to suggest that the furanonaphthoquinones do not serve primarily as DNA intercalators, because if this were the case, they would have been expected to show an increased activity on conversion to their hydroxyamino side chain derivatives.

  DOI：

  10.1021/np9900019
• 作为产物：
  描述：

  3-糠酸 在 正丁基锂 、 三甲基氯硅烷 、 二异丙胺 、 sodium iodide 作用下， 以 乙腈 为溶剂， 反应 1.08h， 生成 2-(3-methoxybenzyl)-3-furoic acid
  参考文献：
  名称：

  细胞毒性呋喃萘醌的合成：地丹单酮和2-乙基呋喃萘醌的区域特异性合成

  摘要：

  Diodantunezone首先从马Lan丹（马鞭草科）中分离出来，最初分配为8-hydroxy-4,9-dihydronaphtho [2,3 - b ] furan-4,9-dione 1a，但后来将其结构修改为5-hydroxy-4 ，9-二氢萘并[2,3- b ]呋喃-4,9-二酮2a。描述了地丹单酮2a及其甲基醚5-甲氧基-4,9-二氢萘并[2,3 - b ]呋喃-4,9-二酮2b的区域特异性合成。还描述了两个2-乙基呋喃萘醌14a和14b的制备。已显示所有四个醌对三种细胞系均具有细胞毒活性（1.3–17.4μmoldm -3）。

  DOI：

  10.1016/s0040-4020(97)00030-6

文献信息

• The birch reduction of heterocyclic compounds V Birch reduction of 2- and 5-acylfuran-3-carboxylic acids and reductive elimination of 2-(arylmethoxymethyl)furan-3-carboxylic acids
  作者：Yasuo Ohta、Matsumi Doe、Yoshiki Morimoto、Takamasa Kinoshita

  DOI：10.1002/jhet.5570370414

  日期：2000.7

  The Birch reduction of 2- and 5-acylfuran-3-carboxylic acid 1 and 4 gave 2-acyl-2,3-dihydrofuran-3-carboxylic acid 2 and 5-acyltetrahydrofuran-3-carboxylic acid 5, respectively. Further examination of the reductive elimination was also studied on 2-(arylmethoxymethyl)furan-3-carboxylic acids 7.

  2-和5-酰基呋喃-3-羧酸1和4的桦木还原分别得到2-酰基-2，3-二氢呋喃-3-羧酸2和5-酰基四氢呋喃-3-羧酸5。还对2-（芳基甲氧基甲基）呋喃-3-羧酸7进行了进一步的还原消除研究。
• The Rapid Reduction of α,α-Diaryl Alcohols To The Corresponding Alkanes Using lodotrimethylsilane
  作者：Philip J Perry、Vasilios H Pavlidis、lan G C Coutts

  DOI：10.1080/00397919608003868

  日期：1996.1

  The utility of iodotrimethylsilane has been extended to include the rapid and highly selective reduction of alpha,alpha-diaryl alcohols. The reduction of a series of alpha-hydroxyfuroic acids in near quantitative yield has been demonstrated and the mechanism discussed.
• Synthesis of Furanonaphthoquinones with Hydroxyamino Side Chains
  作者：Chongming Wu、Randall K. Johnson、Michael R. Mattern、Jackson C. Wong、David G. I. Kingston

  DOI：10.1021/np9900019

  日期：1999.7.1

  Several furanonaphthoquinones have shown useful activity in a yeast assay for DNA-damaging agents and cytotoxicity in mammalian cell culture assays. These results, together with the planar aromatic character of the furanonaphthoquinones, suggested that they might be acting as DNA intercalators. In an attempt to improve this activity, various analogues containing a hydroxyamino side chain have been synthesized. The analogues were prepared by standard methods, but some unexpected reactions were observed nonetheless. Thus, 8-formyl-5-methoxy-4,9-dihydronaphtho[2,3-b]furan-4,9-dione (24) showed an unusual reactivity toward reductive amination, with the reaction proceeding further to give one of two different cyclized products, depending on the amination reagent used. Bioassay results indicated that only simple furanonaphthoquines showed activity in a yeast assay for DNA-damaging agents; compounds with a substituted hydroxyamino side chain were uniformly inactive in this assay. Most of the compounds with a substituted hydroxyamino side chain on the furan ring did, however, show cytotoxicity, although none of them was any more active than the simple aldehyde 2-formyl-4,9-dihydronaphtho[2,3-b]furan-4,9-dione (14). This evidence tends to suggest that the furanonaphthoquinones do not serve primarily as DNA intercalators, because if this were the case, they would have been expected to show an increased activity on conversion to their hydroxyamino side chain derivatives.
• Synthesis of cytotoxic furonaphthoquinones: Regiospecific synthesis of diodantunezone and 2-ethylfuronaphthoquinones
  作者：Philip J Perry、Vasilios H Pavlidis、John A Hadfield

  DOI：10.1016/s0040-4020(97)00030-6

  日期：1997.3

  achyrantifolia (Verbenaceae) and originally assigned as 8-hydroxy-4,9-dihydronaphtho[2,3-b]furan-4,9-dione 1a but its structure was later revised to 5-hydroxy-4,9-dihydronaphtho[2,3-b]furan-4,9-dione 2a. The regiospecific synthesis of diodantunezone 2a and its methyl ether, 5-methoxy-4,9-dihydronaphtho[2,3-b]furan-4,9-dione 2b, is described. The preparation of two 2-ethylfuronaphthoquinones 14a and 14b

  Diodantunezone首先从马Lan丹（马鞭草科）中分离出来，最初分配为8-hydroxy-4,9-dihydronaphtho [2,3 - b ] furan-4,9-dione 1a，但后来将其结构修改为5-hydroxy-4 ，9-二氢萘并[2,3- b ]呋喃-4,9-二酮2a。描述了地丹单酮2a及其甲基醚5-甲氧基-4,9-二氢萘并[2,3 - b ]呋喃-4,9-二酮2b的区域特异性合成。还描述了两个2-乙基呋喃萘醌14a和14b的制备。已显示所有四个醌对三种细胞系均具有细胞毒活性（1.3–17.4μmoldm -3）。