6-(Iodomethyl)hexanolide | 145147-77-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 6-(Iodomethyl)hexanolide
• 英文别名: 7-(iodomethyl)oxepan-2-one；7-(Iodomethyl)-2-oxepanone
• CAS: 145147-77-9
• 化学式: C₇H₁₁IO₂
• 分子量: 254.068
• InChiKey: UPCYMGPAIVROLN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  6-庚烯酸 在 4-二甲氨基吡啶 、 bis(4-methoxyphenyl)selenide 、 N-碘代丁二酰亚胺 、 碳酸氢钠 作用下， 以 氯仿 为溶剂， 反应 16.25h， 以54%的产率得到6-(Iodomethyl)hexanolide
  参考文献：
  名称：

  有机硒和DMAP共催化：从未活化的烯烃区域选择性合成中等大小的内酯和溴氧杂环丁烷

  摘要：

  已经开发了由双（4-甲氧基苯基）硒化物和4-（二甲基氨基）吡啶（DMAP）组成的催化体系，用于区域选择性合成具有高跨环应变的中型溴/碘内酯和溴氧杂环丁烷。77Se NMR，质谱...

  DOI：

  10.1039/c5cc10245f

文献信息

• Efficient Medium Ring Size Bromolactonization Using a Sulfur-Based Zwitterionic Organocatalyst
  作者：Yi An Cheng、Tao Chen、Chong Kiat Tan、Jun Jie Heng、Ying-Yeung Yeung

  DOI：10.1021/ja307210n

  日期：2012.10.10

  Catalytic bromolactonization of long-chain olefinic acids resulting in the efficient synthesis of medium-sized lactones is reported using a zwitterionic catalyst and stoichiometric N-bromosuccinimide halogen source. The reaction was found to be more efficient at 0 degrees C than at room temperature, which could be attributed to the temperature dependence of the zwitterionic catalyst.
• Oxygen Effect in the Iodo Lactonization of Unsaturated Carboxylic Acids Leading to 7- to 12-Membered Ring Lactones
  作者：Bruno Simonot、Gerard Rousseau

  DOI：10.1021/jo00099a019

  日期：1994.10

  The reaction of omega-alkenoic acids with bis(sym-collidine)iodine(I) hexafluorophosphate led to (iodomethyl) epsilon-caprolactones in good yields (49-75%) and medium ring iodo lactones in low yields (4-5%). The latter compounds have been obtained after introduction of an oxygen atom in the carbon chain. The position of the oxygen appeared important. This oxygen effect was explained by the stabilization of the intermediate iodonium ion by the oxygen atom.
• Preparation of seven-membered and medium-ring lactones by iodo lactonization
  作者：Bruno Simonot、Gerard Rousseau

  DOI：10.1021/jo00053a002

  日期：1993.1

  Iodo lactonization of 6-heptenoic acid using bis(sym-collidine)iodine(I) hexafluorophosphate in methylene chloride led in high yield to 6-(iodomethyl)-hexanolide while with longer omega-ethylenic carboxylic acids the corresponding lactones were obtained in low yields; however, the presence of an oxygen atom in the carbon chain allowed the formation of medium-ring iodo lactones.
• Organoselenium and DMAP co-catalysis: regioselective synthesis of medium-sized halolactones and bromooxepanes from unactivated alkenes
  作者：Ajay Verma、Sadhan Jana、Ch. Durga Prasad、Abhimanyu Yadav、Sangit Kumar

  DOI：10.1039/c5cc10245f

  日期：——

  A catalytic system consisting of bis(4-methoxyphenyl)selenide and 4-(dimethylamino)pyridine (DMAP) has been developed for the regioselective synthesis of medium-sized bromo/iodo lactones and bromooxepanes possessing high transannular strain. 77Se NMR, mass spectrometry...

  已经开发了由双（4-甲氧基苯基）硒化物和4-（二甲基氨基）吡啶（DMAP）组成的催化体系，用于区域选择性合成具有高跨环应变的中型溴/碘内酯和溴氧杂环丁烷。77Se NMR，质谱...