ethyl 2-(4-oxo-3,4-dihydro-2H-chromen-2-yl)acetate | 115085-92-2

• 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-(4-oxo-3,4-dihydro-2H-chromen-2-yl)acetate
• 英文别名: ethyl 3,4-dihydro-4-oxo-2H-1-benzopyran-2-acetate；ethyl 2-(4-oxochroman-2-yl)acetate；ethyl 2-(4-oxochroman-2-yl) acetate；Ethyl 2-(4-oxo-2,3-dihydrochromen-2-yl)acetate
• CAS: 115085-92-2
• 化学式: C₁₃H₁₄O₄
• 分子量: 234.252
• InChiKey: MMJIBTAYSXAVPX-UHFFFAOYSA-N

物化性质

• 沸点：
  68-70 °C
• 密度：
  1.183±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 2-(4-oxo-3,4-dihydro-2H-chromen-2-yl)acetate 以80%的产率得到6-nitro-4-oxo-chroman-2-yl-acetic acid (ethyl ester)
  参考文献：
  名称：

  Methods for producing chiral chromones, chromanes, amino substituted chromanes and intermediates therefor

  摘要：

  揭示了生产富含至少一种(2R或2S)对映体的香豆素组合物的工艺步骤和新型工艺，优选为香豆素-2-基羧酸化合物和香豆素-2-基羧酸酯，它们是生产血小板聚集抑制剂的中间体和/或本身是有效的血小板聚集抑制剂。进一步揭示了用于解析手性中间体或最终产品以提供所需对映体的酶促过程。

  公开号：

  US20040053992A1
• 作为产物：
  描述：

  2'-羟基苯乙酮 在 三氟甲磺酸三甲基硅酯 、 sodium hydride 作用下， 以 二氯甲烷 为溶剂， 反应 3.5h， 生成 ethyl 2-(4-oxo-3,4-dihydro-2H-chromen-2-yl)acetate
  参考文献：
  名称：

  Access to 2-alkyl chromanones via a conjugate addition approach

  摘要：

  The introduction of alkyl substituents at C-2 of chromanones via conjugate addition of silyl enol ethers to a variety of chromenones is reported. In most cases racemic 2-alkyl chromanones were obtained in good yield in the presence of TMSOTf. The copper(II)-promoted conjugate addition of silyl enol ethers to chromenones was also carried out, albeit in low yields and no selectivity. Reliable syntheses of the chromenones via acylation of the corresponding beta-diketo-compounds are also described. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.05.115

文献信息

• Reaction of 4-t-butyldimethylsiloxy-1-benzopyrylium salt with enol silyl ethers and active methylenes
  作者：Hideharu Iwasaki、Takashi Kume、Yohsuke Yamamoto、Kin-ya Akiba

  DOI：10.1016/s0040-4039(01)91372-3

  日期：1987.1

  4-t-Butyldimethylsiloxy-l-benzopyrylium salt () was prepared in situ from chromone () and t-butyldimethylsilyl trillate and the salt reacted with enol silyl ethers, ketene silyl acetals and active methylene compounds to afford 2-substituted 4-t-butyldimethylsiloxy-2H-1-benzopyrans () in high yield. These products reacted with acid chlorides and an iminium salt to give 2,3-disubstituted 2,3-dihydro-

  由色酮（）和叔丁基二甲基甲硅烷基三甲酸酯原位制备4-叔丁基二甲基甲硅烷氧基-1-苯并benzo鎓盐（），并使该盐与烯醇甲硅烷基醚，乙烯酮甲硅烷基乙缩醛和活性亚甲基化合物反应，得到2-取代的4-叔丁醇丁基二甲基甲硅烷氧基-2H-1-苯并吡喃（），收率高。这些产物与酰氯和亚胺盐反应，得到2，3-二取代的2，3-二氢-4H-1-苯并吡喃-4-酮。
• Heterodiene cycloadditions: Preparation and transformations of some substituted pyrano[4,3-b][1]benzopyrans
  作者：Simon J. Coutts、Timothy W. Wallace

  DOI：10.1016/s0040-4020(01)85668-4

  日期：1994.1

  Heterodiene cycloadditions of 4-oxo-4H-1-benzopyrans with formyl, acetyl, or carboxyl substituents at C-3 to 1-alkoxy- or 1,1-dialkoxyalkenes produce 3-alkoxy- or 3,3-dialkoxy-4,4a- dihydropyrano[4,3-b][1]benzopyran-10-ones which are capable of a variety of selective transformations, including acid-induced epimerisation and/or retro-cycloaddition, reduction, hydrolysis and alcoholysis, in some cases

  4-氧代-4 H -1-苯并吡喃在C-3处具有甲酰基，乙酰基或羧基取代基的异二烯环加成反应会生成3-烷氧基-或3,3-二烷氧基-4， 4a-二氢吡喃并[4,3- b ] [1]苯并吡喃-10-酮，在某些情况下，能够在多种条件下进行多种选择性转化，包括酸诱导的差向异构和/或逆环加成，还原，水解和醇解非常温和的条件。
• One-pot reaction of ortho-acylphenols and terminal alkynoates for synthesis of 2-alkyl-substituted chromanones
  作者：Ling-Guo Meng、Hui-Fang Liu、Jian-Long Wei、Sun-Na Gong、Song Xue

  DOI：10.1016/j.tetlet.2010.01.093

  日期：2010.3

  A facile synthesis of 2-alkyl-substituted chromanones from ortho-acylphenols and terminal alkynoates is described. The method contains two consecutive processes in one-pot reaction through a DABCO-catalyzed condensation reaction and a KOBu'-mediated intramolecular cycloaddition to afford the desired products. (C) 2010 Elsevier Ltd. All Fights reserved.
• IWASAKI, HIDEHARU;KUME, TAKASHI;YAMAMOTO, YOHSUKE;AKIBA, KIN-YA, TETRAHEDRON LETT., 28,(1987) N 50, 6355-6358
  作者：IWASAKI, HIDEHARU、KUME, TAKASHI、YAMAMOTO, YOHSUKE、AKIBA, KIN-YA

  DOI：——

  日期：——
• METHODS FOR PRODUCING CHIRAL CHROMONES, CHROMANES, AMINO SUBSTITUTED CHROMANES AND INTERMEDIATES THEREFOR
  申请人：MILLENIUM PHARMACEUTICALS, INC.

  公开号：EP1292589A2

  公开（公告）日：2003-03-19