methyl 3-(2H-1,3-benzodioxol-5-yl)-2-methyl-3-oxopropanoate | 42267-23-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: methyl 3-(2H-1,3-benzodioxol-5-yl)-2-methyl-3-oxopropanoate
• 英文别名: α-(3,4-Methylendioxy)-benzoyl-propionsaeure-methylester；Methyl 3-(1,3-benzodioxol-5-yl)-2-methyl-3-oxopropanoate
• CAS: 42267-23-2
• 化学式: C₁₂H₁₂O₅
• 分子量: 236.224
• InChiKey: PLPJQKKNIOKFLQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 3-(2H-1,3-benzodioxol-5-yl)-2-methyl-3-oxopropanoate 在 一水合肼 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以65%的产率得到5-(2H-1,3-benzodioxol-5-yl)-4-methyl-2,3-dihydro-1H-pyrazol-3-one
  参考文献：
  名称：

  Morita–Baylis–Hillman adducts as building blocks of heterocycles: a simple approach to 4-substituted pyrazolones, and mechanism investigation via ESI–MS(/MS)

  摘要：

  We describe herein an efficient approach for the preparation of 4-substituted 2,3-dihydro-1H-pyrazol-3-ones starting from Morita-Baylis-Hillman adducts. These heterocycles were obtained in two or three steps as single isomers with moderate to good overall yields. One efficient and alternative methodology for the synthesis of alpha-methyl-beta-ketoesters is also reported (up to 91 % yield). Additionally, the mechanism of formation of pyrazolones was investigated employing ESI-MS/MS reaction monitoring.

  DOI：

  10.1007/s00706-015-1427-6
• 作为产物：
  描述：

  methyl 3-hydroxy-2-methylene-3-[(3,4-methylenedioxy)phenyl]propanoate 在 dimethyl sulfide borane 、 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 0.25h， 生成 methyl 3-(2H-1,3-benzodioxol-5-yl)-2-methyl-3-oxopropanoate
  参考文献：
  名称：

  Morita–Baylis–Hillman adducts as building blocks of heterocycles: a simple approach to 4-substituted pyrazolones, and mechanism investigation via ESI–MS(/MS)

  摘要：

  We describe herein an efficient approach for the preparation of 4-substituted 2,3-dihydro-1H-pyrazol-3-ones starting from Morita-Baylis-Hillman adducts. These heterocycles were obtained in two or three steps as single isomers with moderate to good overall yields. One efficient and alternative methodology for the synthesis of alpha-methyl-beta-ketoesters is also reported (up to 91 % yield). Additionally, the mechanism of formation of pyrazolones was investigated employing ESI-MS/MS reaction monitoring.

  DOI：

  10.1007/s00706-015-1427-6

文献信息

• 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。
• OHTA SHUNSAKU; HAYAKAWA SATOSHI; NISHIMURA KAZUKO; OKAMOTO MASAO, CHEM. AND PHARM. BULL., 35,(1987) N 3, 1058-1069
  作者：OHTA SHUNSAKU、 HAYAKAWA SATOSHI、 NISHIMURA KAZUKO、 OKAMOTO MASAO

  DOI：——

  日期：——
• Morita–Baylis–Hillman adducts as building blocks of heterocycles: a simple approach to 4-substituted pyrazolones, and mechanism investigation via ESI–MS(/MS)
  作者：Rosimeire C. Barcelos、Lucas A. Zeoly、Manoel T. Rodrigues、Bruno R. V. Ferreira、Marcos N. Eberlin、Fernando Coelho

  DOI：10.1007/s00706-015-1427-6

  日期：2015.9

  We describe herein an efficient approach for the preparation of 4-substituted 2,3-dihydro-1H-pyrazol-3-ones starting from Morita-Baylis-Hillman adducts. These heterocycles were obtained in two or three steps as single isomers with moderate to good overall yields. One efficient and alternative methodology for the synthesis of alpha-methyl-beta-ketoesters is also reported (up to 91 % yield). Additionally, the mechanism of formation of pyrazolones was investigated employing ESI-MS/MS reaction monitoring.