ethyl 2-(chloromethyl)-2-hydroxy-6-methoxy-2H-1-benzopyran-3-carboxylate | 1278587-65-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: ethyl 2-(chloromethyl)-2-hydroxy-6-methoxy-2H-1-benzopyran-3-carboxylate
• 英文别名: ethyl 2-(chloromethyl)-2-hydroxy-6-methoxy-2H-chromene-3-carboxylate
• CAS: 1278587-65-7
• 化学式: C₁₄H₁₅ClO₅
• 分子量: 298.723
• InChiKey: YTXYEYGPEIYGGI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.96
• 重原子数：
  20.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  64.99
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  ethyl 2-(chloromethyl)-2-hydroxy-6-methoxy-2H-1-benzopyran-3-carboxylate 在 三乙基硅烷 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 以82 %的产率得到ethyl 2-(chloromethyl)-6-methoxy-4H-chromene-3-carboxylate
  参考文献：
  名称：

  Synthesis of ethyl 2-((4-phenyl-1H-1,2,3-triazol-1-yl)methyl)-4H/2H-chromene-3-carboxylates by cycloaddition of ethyl 2-(azidomethyl)-4H-chromene-3-carboxylates with alkynes

  摘要：

  DOI：

  10.56042/ijc.v61i8.63519
• 作为产物：
  描述：

  2-羟基-5-甲氧基苯甲醛 、 4-氯乙酰乙酸乙酯 在 哌啶 作用下， 以 二氯甲烷 为溶剂， 反应 14.0h， 以42%的产率得到ethyl 2-(chloromethyl)-2-hydroxy-6-methoxy-2H-1-benzopyran-3-carboxylate
  参考文献：
  名称：

  轻松合成取代的2-（氯甲基）-2-羟基-2-羟基-2H-1-苯并吡喃-3-羧酸乙酯

  摘要：

  在有哌啶的CH 2 Cl 2存在下，取代的水杨醛与4-氯-3-氧代丁酸乙酯反应，合成了2-（氯甲基）-2-羟基-2 H-亚铬基-3-羧酸乙酯2a – 2j。在室温下，收率良好。

  DOI：

  10.1002/hlca.201000181

文献信息

• Wittig homologation of 2-(chloromethyl)-2H-chromen-2-ol derivatives: a new facile synthesis of substituted 2,3-dihydrobenzoxepine-4-carboxylates
  作者：Bhimapaka China Raju、Gannerla Saidachary、Jaladi Ashok Kumar

  DOI：10.1016/j.tet.2012.05.047

  日期：2012.8

  homologation of 2-(chloromethyl)-2H-chromen-2-ol derivatives 2a–t with (ethoxycarbonylmethylene)triphenylphosphorane provided the 2-oxoethylidene-2,3-dihydrobenzoxepine-4-carboxy-lates 3a–t with Z (cis) selectivity. Various basic catalysts were studied for the reaction of 2-(chloromethyl)-2H-chromen-2-ol 2a with the combination of Wittig reagent to provide compound 3b. The reaction of 2-(chloromethyl)-2H-chromen-2-ol

  维蒂希的2-（氯甲基）-2同系ħ -苯并吡喃-2-醇衍生物2A -吨与（乙氧基羰基亚甲基）三苯基正膦中提供的2氧代亚乙基-2,3- dihydrobenzoxepine -4-羧基酸酯3A -吨与Ž（顺）的选择性。研究了各种碱性催化剂，用于2-（氯甲基）-2 H-铬-2-醇2a与Wittig试剂的反应，得到化合物3b。2-（氯甲基）-2 H -chromen-2-ol 2a的反应与其他Wittig试剂，例如亚甲基（三亚苯基）膦和（1-乙氧基羰基亚乙基）三苯基膦，提供了酮衍生物4a而不是2-氧代亚乙基衍生物3b。使酮衍生物4a与Wittig试剂（乙氧基羰基亚甲基）三苯基膦烷反应，得到2，3-二氢苯并二甲苯基-4-羧酸酯3b。本方法是新颖的，直接的，并且是首次报道。
• A facile construction of oxygen heterocycles by the reaction of benzoxepine-4-carboxylates with dihaloalkanes and activated alkynes
  作者：Veera Prasad Kasagani、Siva Hariprasad Kurma、China Raju Bhimapaka

  DOI：10.1039/c9ob00769e

  日期：——

  This manuscript describes the preparation of heterocyclic compounds such as naphtho[1,3]-dioxoles (3a-h), [1,4]-dioxines (4a-h), [1,4]-dioxepines (5a-c), [1,4]-dioxocines (6a-c) and diethyl 2-(2-ethoxy-2-oxoethyl)naphtho[1,3]dioxoles (8a-f). These heterocyclic compounds have been achieved by the reaction of benzoxepine-4-carboxylates (1a-h) with dihaloalkanes (2a-e) and activated alkyne (7a) for the

  该手稿描述了杂环化合物的制备，例如萘并[1,3]-二恶唑（3a-h），[1,4]-二恶英（4a-h），[1,4]-二氧杂庚环（5a-c）， [1，4]-二氧杂环酮（6a-c）和2-（2-乙氧基-2-氧代乙基）萘二乙基[1，3]二恶唑（8a-f）。这些杂环化合物是通过苯并xepine-4-羧酸盐（1a-h）与二卤代烷烃（2a-e）和活化炔烃（7a）的首次反应获得的。这项工作代表了通过一步法形成CC和CO键来构建实用氧杂环的第一个例子。
• Convenient one-pot synthesis, anti-mycobacterial and anticancer activities of novel benzoxepinoisoxazolones and pyrazolones
  作者：G. Saidachary、K. Veera Prasad、D. Divya、Ashita Singh、U. Ramesh、B. Sridhar、B. China Raju

  DOI：10.1016/j.ejmech.2014.02.042

  日期：2014.4

  Series of new benzoxepinoisoxazolones 4a-d and pyrazolones 6a-t were prepared by the cyclocondensation of substituted (E)-ethyl 3-oxo-2,3-dihydrobenzo[b]oxepine-4-carboxylates 3a-d with hydroxylamine hydrochloride and phenylhydrazine hydrochlorides 5a-k. Synthesized compounds were screened for their in vitro anti-mycobacterial activity and anticancer activity. Ten compounds displayed good anti-mycobacterial activity, among these; compound 4d and 6b found to be potent when compared to standard drug isoniazid. Eleven compounds displayed good anticancer activity and compounds 4b-d displayed equipotent activity on HeLa cell lines when compared to standard drug doxorubicin. Activation of caspase-3 and caspase-9 has been measured for compounds 4b-d on HeLa cell lines (apoptosis). This is the first report assigning in vitro anti-mycobacterial, anticancer and structure-activity relationship for this new class of benzoxepinoisoxazolones and pyrazolones. (C) 2014 Elsevier Masson SAS. All rights reserved.