3-(4-Bromo-phenyl)-oxirane-2,2-dicarboxylic acid diethyl ester | 58070-02-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-(4-Bromo-phenyl)-oxirane-2,2-dicarboxylic acid diethyl ester
• 英文别名: diethyl 3-(4-bromophenyl)oxirane-2,2-dicarboxylate
• CAS: 58070-02-3
• 化学式: C₁₄H₁₅BrO₅
• 分子量: 343.174
• InChiKey: HXJHYGPRGOMVFX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.39
• 重原子数：
  20.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  65.13
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  苯并噻唑 、 3-(4-Bromo-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78%的产率得到diethyl 1-(4-bromophenyl)-3,3-dimethyl-3,3a-dihydro-1H-benzo[4,5]thiazolo[3,2-c]oxazole
  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：

  diethyl 2-(4-bromobenzylidene)malonate 、 双氧水 生成 3-(4-Bromo-phenyl)-oxirane-2,2-dicarboxylic acid diethyl ester
  参考文献：
  名称：

  KULKARNI B. D.; RAO A. S., INDIAN J. CHEM. , 1975, 13, NO 10, 1097-1098

  摘要：

  DOI：

文献信息

• Chemo- and regioselective ring-opening of donor–acceptor oxiranes with <i>N</i>-heteroaromatics
  作者：Ji-Wei Sang、Ming-Sheng Xie、Man-Man Wang、Gui-Rong Qu、Hai-Ming Guo

  DOI：10.1039/d1cc00600b

  日期：——

  The first ring-opening of D–A oxiranes with N-heteroaromatics in a chemoselective C–C bond cleavage manner was achieved. In the presence of 5 mol% of Y(OTf)3 as the catalyst, diverse N-heteroaromatics, including benzotriazoles, purines, substituted benzimidazole, imidazole and pyrazole, reacted well with various D–A oxiranes, providing acyclic nucleoside analogues containing a N-glycosidic bond in

  通过化学选择性的C-C键裂解，实现了带有N-杂芳族化合物的D–A肟基的第一个开环反应。在存在5 mol％的Y（OTf）3作为催化剂的情况下，各种N-杂芳族化合物，包括苯并三唑，嘌呤，取代的苯并咪唑，咪唑和吡唑，与各种D-A肟酯反应良好，提供了含有N的无环核苷类似物-糖苷键的产率高达97％，区域选择性高达> 95：5。通过简单的转化，也可以得到更昔洛韦类似物。
• Asymmetric catalytic [4+3] cycloaddition of <i>ortho</i>-quinone methides with oxiranes
  作者：Qingfa Tan、Han Yu、Yao Luo、Fenzhen Chang、Xiaohua Liu、Yuqiao Zhou、Xiaoming Feng

  DOI：10.1039/d1cc00262g

  日期：——

  Catalytic enantioselective [4+3] cycloaddition reaction between o-quinone methides and oxiranes was achieved by using a chiral N,N′-dioxide/TbIII complex as the catalyst, affording medium-sized hydrodioxepine derivatives in high yields (up to 99%) with good to excellent diastereo-(up to 94 : 6 dr) and enantioselectivities (up to 97% ee). The topographic steric maps and distribution of the buried volume

  以手性N，N'-二氧化物/ Tb III络合物为催化剂，实现邻醌甲基化物与环氧乙烷之间的催化对映选择性[4 + 3]环加成反应，得到高收率的中型氢二氧杂环庚烷衍生物（高达99％ ）具有良好至优异的非对映体-（高达94：6 dr）和对映选择性（高达97％ee）。通过Cavallo的SambVca 2工具收集了拓扑空间图和催化剂的埋藏量（％V Bur）分布，以有效表示手性N，N'-二氧化物的金属配合物的手性口袋。
• Cyclization Reaction of Donor–Acceptor Oxiranes with <i>N,N′</i>-Disubstituted Thioureas: A Domino Process to <i>trans</i>-Dihydropyrimidines
  作者：Jing Wang、Qi-Ying Zhang、Ming-Sheng Xie、Dong-Chao Wang、Gui-Rong Qu、Hai-Ming Guo

  DOI：10.1021/acs.orglett.8b02930

  日期：2018.10.19

  An unprecedented cyclization reaction of donor–acceptor oxiranes with N,N′-disubstituted thioureas to construct trans-dihydropyrimidines is presented. Preliminary reaction mechanism studies demonstrated that the reaction underwent sequential cycloaddition/amine ester exchange/oxygen–sulfur exchange/desulfuration/Michael addition process. A wide range of trans-dihydropyrimidines were produced with high

  提出了空前的供体-受体环氧乙烷与N，N'-二取代的硫脲环化反应，以构建反式-二氢嘧啶的环化反应。初步的反应机理研究表明，该反应按顺序进行了环加成反应/胺酯交换反应/氧硫交换反应/脱硫反应/迈克尔加成反应过程。通过使用这种方法，以高达94％的高产率生产了各种各样的反式-二氢嘧啶。
• Highly Chemoselective Synthesis of Purino[3,2-<i>c</i>]oxazoles via the Asymmetric Dearomative [3+2] Cycloaddition of Purines with Donor–Acceptor Oxiranes
  作者：Meng-Cheng Zhang、Dong-Chao Wang、Hai-Ting Wang、Gui-Rong Qu、Hai-Ming Guo

  DOI：10.1021/acs.orglett.2c02773

  日期：2022.10.21

  donor–acceptor oxiranes was developed. This reaction, which proceeds via highly chemoselective C–C bond cleavage of the oxiranes, accesses chiral purino[3,2-c]oxazole compounds (≤99% ee after enrichment via crystallization). The electronic effects of the purine ring determine the reactivity of the substrate. The general applicability of this method was illustrated by gram-scale synthesis, the diverse

  开发了 Ni(II)/双恶唑啉催化的取代嘌呤与供体-受体环氧乙烷的不对称脱芳烃 [3+2] 环加成反应。该反应通过环氧乙烷的高度化学选择性 C-C 键断裂进行，获得手性嘌呤 [3,2- c ] 恶唑化合物（通过结晶富集后 ee ≤99%）。嘌呤环的电子效应决定了底物的反应性。这种方法的普遍适用性通过克级合成、产品的多样化转化以及所选衍生物的有前途的生物活性来说明。