ethyl 2-(chloromethyl)-2-hydroxy-2H-chromene-3-carboxylate | 1278587-62-4

• 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-2H-chromene-3-carboxylate
• 英文别名: ethyl 2-(chloromethyl)-2-hydroxychromene-3-carboxylate
• CAS: 1278587-62-4
• 化学式: C₁₃H₁₃ClO₄
• 分子量: 268.697
• InChiKey: JKSQHSQUKZBXMO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 2-(chloromethyl)-2-hydroxy-2H-chromene-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80 %的产率得到ethyl 2-(chloromethyl)-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：

  4-氯乙酰乙酸乙酯 、 水杨醛 在 哌啶 作用下， 以 二氯甲烷 为溶剂， 生成 ethyl 2-(chloromethyl)-2-hydroxy-2H-chromene-3-carboxylate
  参考文献：
  名称：

  2-（氯甲基）-2 H -chromen-2-ol衍生物的Wittig同源性：取代的2,3-二氢苯并二甲苯-4-羧酸酯的新合成

  摘要：

  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。

  DOI：

  10.1016/j.tet.2012.05.047

文献信息

• A Novel Approach for C–C, C–N, and C–O Bond Formation Reactions: A Facile Synthesis of Benzophenazine, Quinoxaline, and Phenoxazine Derivatives via Ring Opening of Benzoxepines
  作者：Bhimapaka China Raju、Kasagani Veera Prasad、Gannerla Saidachary、Balasubramanian Sridhar

  DOI：10.1021/ol4033122

  日期：2014.1.17

  synthesis of benzophenazine, quinoxaline, and phenoxazine derivatives by the reaction of benzoxepine-4-carboxylates with benzene-1,2-diamines, ethane-1,2-diamine, and 2-aminophenols in the presence of Bi(OTf)3 (5 mol %) under mild conditions in very good yields. The present protocol opens a new way for C–C, C–N, and C–O bond-formation reactions in a single-step process. The structural assignment was

  已开发出一种新的一锅操作规程，用于通过苯并氧杂庚酸酯-4-羧酸盐与苯-1,2-二胺，乙烷-1,2-二胺和2-氨基苯酚的反应来合成苯并吩嗪，喹喔啉和苯恶嗪衍生物在温和的条件下在Bi（OTf）3（5 mol％）存在下以非常好的收率。本协议为单步过程中C–C，C–N和C–O键形成反应开辟了一条新途径。通过X射线分析确认了结构分配。
• 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。
• Facile Synthesis of Substituted Ethyl 2-(Chloromethyl)-2-hydroxy-2H-1-benzopyran-3-carboxylates
  作者：Bhimapaka China Raju、Gannerla Saidachary、Jaladi Ashok Kumar、Balasubramanian Sridhar

  DOI：10.1002/hlca.201000181

  日期：2011.2

  Ethyl 2‐(chloromethyl)‐2‐hydroxy‐2H‐chromene‐3‐carboxylates 2a–2j have been synthesized by reaction of substituted salicylaldehydes with ethyl 4‐chloro‐3‐oxobutanoate, in the presence of piperidine in CH2Cl2 at room temperature, in good yields.

  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。
• BF₃·OEt₂-catalyzed synthesis of 2,2′-spirobi-2<i>H</i>-1-benzopyrans from 2<i>H</i>-chromenes
  作者：Sairam Mudulkar、Sai Teja Kolla、Balasubramanian Sridhar、China Raju Bhimapaka

  DOI：10.1039/d2ob01286c

  日期：——

  A new BF3·OEt2-catalyzed approach was developed for the construction of 2,2′-spirobi-2H-1-benzopyrancarboxylates by reacting ethyl 2-(chloromethyl)-2-hydroxy-2H-chromene-3-carboxylates with salicylaldehydes. The reactions proceeded through the formation of C–C and C–O bonds in one pot. Structure assignment of compound 3c was confirmed by single crystal X-ray analysis.

  2-(氯甲基)-2-羟基-2 H-色烯-3-羧酸乙酯反应开发了一种新的BF 3 ·OEt 2催化方法用于构建2,2'-螺双-2 H -1-苯并吡喃羧酸盐与水杨醛。反应通过在一锅中形成C-C和C-O键进行。通过单晶 X 射线分析证实了化合物3c的结构分配。
• 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.