3-(4-Methoxy-phenyl)-oxirane-2,2-dicarboxylic acid diethyl ester | 58070-03-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-(4-Methoxy-phenyl)-oxirane-2,2-dicarboxylic acid diethyl ester
• 英文别名: diethyl 3-(4-methoxyphenyl)oxirane-2,2-dicarboxylate
• CAS: 58070-03-4
• 化学式: C₁₅H₁₈O₆
• 分子量: 294.304
• InChiKey: WAJHQIYHCRWIPN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.63
• 重原子数：
  21.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  74.36
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  苯并噻唑 、 3-(4-Methoxy-phenyl)-oxirane-2,2-dicarboxylic acid diethyl ester 在 scandium tris(trifluoromethanesulfonate) 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 72.0h， 以94%的产率得到diethyl 1-(4-methoxyphenyl)-1H-benzo[4,5]thiazolo[3,2-c]oxazole-3,3(3aH)-dicarboxylate
  参考文献：
  名称：

  Highly Chemo- and Diastereoselective Dearomative [3 + 2] Cycloaddition Reactions of Benzazoles with Donor–Acceptor Oxiranes

  摘要：

  A Sc(OTf)(3)-catalyzed dearomative [3 + 2] cycloaddition of benzazoles with donor-acceptor oxiranes through chemoselective C-C bond cleavage of oxiranes was developed under mild conditions. This reaction provides an efficient method to construct benzazolo[3,2-c]oxazole compounds in good yields and with high diastereoselectivity. The reaction has a general substrate scope, and the donor-acceptor oxiranes with electron-donating and electron-withdrawing groups on the aromatic ring afforded the desired cycloadducts.

  DOI：

  10.1021/acs.orglett.8b03615
• 作为产物：
  描述：

  4-甲氧基苯甲醛 在 哌啶 、 aluminum oxide 、 sodium hypochlorite 、 溶剂黄146 作用下， 以 水 、 甲苯 、 乙腈 为溶剂， 反应 16.0h， 生成 3-(4-Methoxy-phenyl)-oxirane-2,2-dicarboxylic acid diethyl ester
  参考文献：
  名称：

  Highly Chemo- and Diastereoselective Dearomative [3 + 2] Cycloaddition Reactions of Benzazoles with Donor–Acceptor Oxiranes

  摘要：

  A Sc(OTf)(3)-catalyzed dearomative [3 + 2] cycloaddition of benzazoles with donor-acceptor oxiranes through chemoselective C-C bond cleavage of oxiranes was developed under mild conditions. This reaction provides an efficient method to construct benzazolo[3,2-c]oxazole compounds in good yields and with high diastereoselectivity. The reaction has a general substrate scope, and the donor-acceptor oxiranes with electron-donating and electron-withdrawing groups on the aromatic ring afforded the desired cycloadducts.

  DOI：

  10.1021/acs.orglett.8b03615

文献信息

• KOH-Promoted Synthesis of Oxirane Functional Derivatives from Diethyl Bromomalonate and Aldehydes under Phase-Transfer Catalysis Conditions
  作者：Galina V. Kryshtal、Galina M. Zhdankina、Sergei G. Zlotin

  DOI：10.1016/j.mencom.2013.01.008

  日期：2013.1

  The Darzens condensation of diethyl bromomalonate with aromatic or isoprenoid aldehydes under heterogeneous conditions (KOH/MeCN) in the presence of Bu4NPF6 as a recoverable phase-transfer catalyst afforded the corresponding diethyl 3-R-oxirane-2,2-dicarboxylates in high yields.
• KULKARNI B. D.; RAO A. S., INDIAN J. CHEM. <IJOC-AP>, 1975, 13, NO 10, 1097-1098
  作者：KULKARNI B. D.、 RAO A. S.

  DOI：——

  日期：——