(Z)-2,2-dimethyl-5-((E)-2-oxo-4-phenylbut-3-en-1-ylidene)-1,3-dioxolan-4-one | 1232682-47-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (Z)-2,2-dimethyl-5-((E)-2-oxo-4-phenylbut-3-en-1-ylidene)-1,3-dioxolan-4-one
• CAS: 1232682-47-1
• 化学式: C₁₅H₁₄O₄
• 分子量: 258.274
• InChiKey: TYLOVPMNSRPANK-WOKGKLDWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.46
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (Z)-2,2-dimethyl-5-((E)-2-oxo-4-phenylbut-3-en-1-ylidene)-1,3-dioxolan-4-one 在 sodium hydroxide 作用下， 以 水 为溶剂， 以65%的产率得到(2Z,5E)-2-hydroxy-4-oxo-6-phenylhexa-2,5-dienoic acid
  参考文献：
  名称：

  (Z)-2,2-Dimethyl-5-carboxymethylene-1,3-dioxolan-4-one: a new synthon for the synthesis of α,γ-diketoacid derivatives

  摘要：

  The synthesis and reactivity of (Z)-2,2-dimethyl-5-carboxymethylene-1,3-dioxolan-4-one, a new and versatile synthon useful for the synthesis of selectively protected alpha,gamma-diketoacid derivatives, are described. This new, protected form of hydroxyl fumaric acid along with its acid chloride was used to prepare ester, amide, and aryl derivatives. The dioxolane moiety was found to be a convenient functionality that facilitated ready unmasking by straightforward hydrolysis to reveal alpha,gamma-diketoacid derivatives or derivatization to yield ester, amide, and 2,3-pyrrolidinedione derivatives. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.04.032
• 作为产物：
  描述：

  (Z)-2-(2,2-dimethyl-5-oxo-1,3-dioxolan-4-ylidene)acetyl chloride 、 (E)-1-phenyl-(2-tributylstannyl)ethene 在 双(乙腈)氯化钯(II) 作用下， 以75%的产率得到(Z)-2,2-dimethyl-5-((E)-2-oxo-4-phenylbut-3-en-1-ylidene)-1,3-dioxolan-4-one
  参考文献：
  名称：

  (Z)-2,2-Dimethyl-5-carboxymethylene-1,3-dioxolan-4-one: a new synthon for the synthesis of α,γ-diketoacid derivatives

  摘要：

  The synthesis and reactivity of (Z)-2,2-dimethyl-5-carboxymethylene-1,3-dioxolan-4-one, a new and versatile synthon useful for the synthesis of selectively protected alpha,gamma-diketoacid derivatives, are described. This new, protected form of hydroxyl fumaric acid along with its acid chloride was used to prepare ester, amide, and aryl derivatives. The dioxolane moiety was found to be a convenient functionality that facilitated ready unmasking by straightforward hydrolysis to reveal alpha,gamma-diketoacid derivatives or derivatization to yield ester, amide, and 2,3-pyrrolidinedione derivatives. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.04.032