Methyl 3-(3-bromophenyl)-2-methyl-3-oxopropanoate | 1247559-91-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Methyl 3-(3-bromophenyl)-2-methyl-3-oxopropanoate
• CAS: 1247559-91-6
• 化学式: C₁₁H₁₁BrO₃
• 分子量: 271.111
• InChiKey: JUYOVOIEOBGHTH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Methyl 3-(3-bromophenyl)-2-methyl-3-oxopropanoate 在 盐酸羟胺 、 sodium acetate 作用下， 以 乙醇 为溶剂， 以0.5581 g的产率得到3-(3-bromophenyl)-4-methylisoxazol-5(4H)-one
  参考文献：
  名称：

  异恶唑酮与异氰酸酯的钯催化扩环反应：1,3-氧杂嗪-6-一衍生物的合成

  摘要：

  公开了异恶唑酮与异氰酸酯的钯催化的扩环反应。在反应中，提出了涉及开环/环化的级联过程。该反应由于没有消除CO 2而具有高原子经济性。此外，所获得的产品展示出具有较高固态发射效率的聚集诱发的发射特性。

  DOI：

  10.1002/adsc.202001200
• 作为产物：
  描述：

  3-溴苯甲酰氯 、 丙烯酸甲酯（MA） 在 [Rh(1,5-cyclooctadiene)(P(OPh)3)2]OTf 、 二乙基甲基硅烷 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以86%的产率得到Methyl 3-(3-bromophenyl)-2-methyl-3-oxopropanoate
  参考文献：
  名称：

  Rhodium-catalyzed hydroaroylation of α,β-unsaturated esters using aroyl chlorides and Et2MeSiH

  摘要：

  Hydroaroylation of methyl acrylate 2a to give the alpha-aroyl esters 4 took place in the three-component reaction of 2a, aroyl chlorides 1, and Et2MeSiH in the presence of 1 mol % of [Rh(cod)(PR3)2]OTf (cod = 1,5-cyclooctadiene, OTf = OSO2CF3, R = Ph (3a), OPh (3b)) in CH2Cl2. GC and H-1 NMR investigation revealed that the rhodium-catalyzed hydroaroylation proceeds via two successive transformations, that is, hydrosilylation of 2a to afford silyl enol ether 5a followed by C-C bond formation between 5a and 1a. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.06.009

文献信息

• An Efficient Tertiary Azidation of 1,3-Dicarbonyl Compounds in Water Catalyzed by Tetrabutylammonium Iodide
  作者：Jayaraman Dhineshkumar、Kandikere Ramaiah Prabhu

  DOI：10.1002/ejoc.201501374

  日期：2016.1

  An efficient azidation of 1,3-dicarbonyl compounds led to tertiary azides in the presence of tetrabutylammonium iodide (TBAI). TBAI is used as a pre-catalyst along with aq. tert-butyl hydroperoxide (TBHP) as an oxidant in aqueous medium. This operationally simple, practical, mild and green method provides an opportunity to synthesize a variety of azidated -keto esters, amides, and ketones in good yields

  在四丁基碘化铵 (TBAI) 存在下，1,3-二羰基化合物的有效叠氮化反应生成叔叠氮化物。TBAI 与 aq 一起用作预催化剂。叔丁基过氧化氢 (TBHP) 作为水性介质中的氧化剂。这种操作简单、实用、温和且绿色的方法为以良好的收率合成各种叠氮化酮酯、酰胺和酮提供了机会。
• Palladium Catalyzed Ring Expansion Reaction of Isoxazolones with Isocyanides: Synthesis of 1,3‐Oxazin‐6‐One Derivatives
  作者：Yi‐Ming Zhu、Wan Zhang、Hongkun Li、Xiao‐Ping Xu、Shun‐Jun Ji

  DOI：10.1002/adsc.202001200

  日期：2021.2.2

  A palladium catalyzed ring expansion reaction of isoxazolones with isocyanides was disclosed. In the reaction, a cascade process involving ring‐opening/cyclization was suggested. The reaction features high atomic economy due to no elimination of CO2 occurred. Moreover, products obtained demonstrate aggregation‐induced emission properties with relatively high solid‐state emission efficiencies.

  公开了异恶唑酮与异氰酸酯的钯催化的扩环反应。在反应中，提出了涉及开环/环化的级联过程。该反应由于没有消除CO 2而具有高原子经济性。此外，所获得的产品展示出具有较高固态发射效率的聚集诱发的发射特性。
• Rhodium-catalyzed hydroaroylation of α,β-unsaturated esters using aroyl chlorides and Et2MeSiH
  作者：Takako Muraoka、Eiji Hiraiwa、Minami Abe、Keiji Ueno

  DOI：10.1016/j.tetlet.2013.06.009

  日期：2013.8

  Hydroaroylation of methyl acrylate 2a to give the alpha-aroyl esters 4 took place in the three-component reaction of 2a, aroyl chlorides 1, and Et2MeSiH in the presence of 1 mol % of [Rh(cod)(PR3)2]OTf (cod = 1,5-cyclooctadiene, OTf = OSO2CF3, R = Ph (3a), OPh (3b)) in CH2Cl2. GC and H-1 NMR investigation revealed that the rhodium-catalyzed hydroaroylation proceeds via two successive transformations, that is, hydrosilylation of 2a to afford silyl enol ether 5a followed by C-C bond formation between 5a and 1a. (C) 2013 Elsevier Ltd. All rights reserved.