3-Decyl-cyclobut-3-ene-1,2-dione | 198137-65-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-Decyl-cyclobut-3-ene-1,2-dione
• 英文别名: 3-Decylcyclobut-3-ene-1,2-dione
• CAS: 198137-65-4
• 化学式: C₁₄H₂₂O₂
• 分子量: 222.327
• InChiKey: XCABVPDDBAPHDM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  16
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-十二炔 、 alkaline earth salt of/the/ methylsulfuric acid 在 sodium tetrahydroborate 、 溶剂黄146 作用下， 生成 3-Decyl-cyclobut-3-ene-1,2-dione
  参考文献：
  名称：

  [HFe 3（CO）11 ] -试剂与炔烃的新型反应：环丁烯二酮的新合成

  摘要：

  使用Fe（CO）5和NaBH 4 / CH 3 COOH在THF中与炔烃进行原位生成的[HFe 3（CO）11 ] -物种与炔烃的反应，然后通过CuCl 2 .2H 2 O氧化，在60 ℃生成相应的环丁烯二酮–73％的收益率。

  DOI：

  10.1016/s0040-4039(97)01677-8

文献信息

• Novel Reaction of the [HFe3(CO)11]− reagent with alkynes: A new synthesis of cyclobutenediones
  作者：Mariappan Periasamy、Chellappan Rameshkumar、Ukkiramapandian Radhakrishnan

  DOI：10.1016/s0040-4039(97)01677-8

  日期：1997.10

  Reaction of the [HFe3(CO)11]− species generated in situ using Fe(CO)5 and NaBH4/CH3COOH in THF with alkynes, followed by CuCl2.2H2O oxidation leads to the corresponding cyclobutenediones in 60–73% yields.

  使用Fe（CO）5和NaBH 4 / CH 3 COOH在THF中与炔烃进行原位生成的[HFe 3（CO）11 ] -物种与炔烃的反应，然后通过CuCl 2 .2H 2 O氧化，在60 ℃生成相应的环丁烯二酮–73％的收益率。
• New Convenient One-Pot Methods of Conversion of Alkynes to Cyclobutenediones or α,β-Unsaturated Carboxylic Acids Using Novel Reactive Iron Carbonyl Reagents
  作者：Mariappan Periasamy、Chellappan Rameshkumar、Ukkiramapandian Radhakrishnan、Jean-Jacques Brunet

  DOI：10.1021/jo971929d

  日期：1998.7.1

  Reactions of NaHFe(CO)(4)/RX or [HFe3(CO)(11)](-) reagents with alkynes lead to the formation of the corresponding cr,P-unsaturated carboxylic acids and/or the cyclobutenediones. The reagent; generated in situ using the NaHFe(CO)(4)/CH3I combination in THF, on reaction with alkynes followed by CuCl2. 2H(2)O oxidation, gives the corresponding cyclobutenediones (27-42%) and alpha,beta-unsaturated carboxylic acids (10-22%), whereas the reagent generated using CH2Cl2 in place of CH3I leads to a,P-unsaturated carboxylic acids (37-60%) and their derivatives (35-55%) at 25 degrees C. The same reagent system in the presence of acetic acid (4 equiv) yields the corresponding cyclobutenedione (33%). The reaction using Me3SiCl gives the corresponding alpha,beta-unsaturated carboxylic acids (45-54%) at 25 degrees C and the corresponding cyclobutenediones (51-63%) at 60 degrees C. Interestingly, the reaction of the [HFe3(CO)(11)](-) species generated using Fe(CO)(5)/NaBH4/CH3COOH, with alkynes at 25 degrees C, followed by CuCl2. 2H(2)O oxidation gives the corresponding cyclobutenediones (60-73%). The possible intermediates and pathways for the formation of alpha,beta-unsaturated carboxylic acids and cyclobutenediones are discussed.