2-(5-phenylisoxazol-3-ylmethyl)acrylic acid methyl ester | 831181-22-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2-(5-phenylisoxazol-3-ylmethyl)acrylic acid methyl ester
• 英文别名: Methyl 2-[(5-phenyl-1,2-oxazol-3-yl)methyl]prop-2-enoate
• CAS: 831181-22-7
• 化学式: C₁₄H₁₃NO₃
• 分子量: 243.262
• InChiKey: RUBYRIQYJLBEHS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  52.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(5-phenylisoxazol-3-ylmethyl)acrylic acid methyl ester 在 镍 氢气 作用下， 以 甲醇 、 乙醇 为溶剂， 20.0 ℃ 、206.84 kPa 条件下， 反应 2.0h， 生成 (Z)-4-Amino-2-(4-methyl-piperazin-1-ylmethyl)-6-oxo-6-phenyl-hex-4-enoic acid methyl ester
  参考文献：
  名称：

  Simple and Efficient Synthesis of Substituted 2-Pyrrolidinones, 2-Pyrrolones, and Pyrrolidines from Enaminones of Baylis−Hillman Derivatives of 3-Isoxazolecarbaldehydes^,

  摘要：

  The enaminones, generated from derivatives of appropriately substituted Baylis-Hillman adducts of 3-isoxazolecarbaldehydes, undergo intramolecular ring-closure reactions to afford substituted 2-pyrrolidinones, 1,5-dihydro-2-pyrrolones, and N-substituted pyrrolidines in good yields.

  DOI：

  10.1021/jo048411b
• 作为产物：
  描述：

  2-[acetoxy(5-phenylisoxazol-3-yl)methyl]acrylic acid methyl ester 在 三乙烯二胺 、 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 0.5h， 以86%的产率得到2-(5-phenylisoxazol-3-ylmethyl)acrylic acid methyl ester
  参考文献：
  名称：

  Simple and Efficient Synthesis of Substituted 2-Pyrrolidinones, 2-Pyrrolones, and Pyrrolidines from Enaminones of Baylis−Hillman Derivatives of 3-Isoxazolecarbaldehydes^,

  摘要：

  The enaminones, generated from derivatives of appropriately substituted Baylis-Hillman adducts of 3-isoxazolecarbaldehydes, undergo intramolecular ring-closure reactions to afford substituted 2-pyrrolidinones, 1,5-dihydro-2-pyrrolones, and N-substituted pyrrolidines in good yields.

  DOI：

  10.1021/jo048411b

文献信息

• Unusual retention of isoxazole ring under the influence of 3-(substituted nitrophenyl)-2-isoxazoline during catalytic hydrogenation of isoxazoline-substituted isoxazole systems
  作者：Vijay Singh、Samiran Hutait、Gaya P. Yadav、Prakas R. Maulik、Sanjay Batra

  DOI：10.1002/jhet.87

  日期：2009.7

  The cleavage of the isoxazole ring during the Raney-Ni-promoted catalytic hydrogenation is prevented under the influence of 3-(substituted nitrophenyl)-2-isoxazoline in isoxazoline-substituted isoxazole systems produced via 1,3-dipolar cycloaddition either on the Baylis–Hillman derivatives or Grignard products. Unexpectedly, the hydrogenations in these diastereomeric compounds were observed to exclusively

  在阮内镍促进的催化加氢过程中，在3-（取代的硝基苯基）-2-异恶唑啉的影响下，异恶唑环的裂解被阻止，该异恶唑啉取代的异恶唑系统是通过在Baylis上的1，3-偶极环加成生成的异恶唑啉取代的异恶唑系统希尔曼衍生品或格利雅产品。出乎意料的是，观察到这些非对映体化合物中的氢化仅产生产物，其中甲氧基羰基和羟基或乙酰基彼此同义地存在。J.杂环化​​学，（2009）。
• Simple and Efficient Synthesis of Substituted 2-Pyrrolidinones, 2-Pyrrolones, and Pyrrolidines from Enaminones of Baylis−Hillman Derivatives of 3-Isoxazolecarbaldehydes^,
  作者：Vijay Singh、Rashmi Saxena、Sanjay Batra

  DOI：10.1021/jo048411b

  日期：2005.1.1

  The enaminones, generated from derivatives of appropriately substituted Baylis-Hillman adducts of 3-isoxazolecarbaldehydes, undergo intramolecular ring-closure reactions to afford substituted 2-pyrrolidinones, 1,5-dihydro-2-pyrrolones, and N-substituted pyrrolidines in good yields.