2(2-iodobenzyl)cyclohexane-1,3-dione | 154371-35-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2(2-iodobenzyl)cyclohexane-1,3-dione
• 英文别名: 2-[(2-Iodophenyl)methyl]cyclohexane-1,3-dione
• CAS: 154371-35-4
• 化学式: C₁₃H₁₃IO₂
• 分子量: 328.15
• InChiKey: DOVIEEAISXXCJK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2(2-iodobenzyl)cyclohexane-1,3-dione 在 吡啶 、 六甲基磷酰三胺 、 正丁基锂 、 palladium 10% on activated carbon 、 氢气 作用下， 以 二氯甲烷 、 甲苯 为溶剂， -78.0~20.0 ℃ 、101.33 kPa 条件下， 反应 0.25h， 生成 6,7,8,11-tetrahydro-5H-benzo[9]annulen-5-one
  参考文献：
  名称：

  Generation of Medium-Ring Cycloalkynes by Ring Expansion of Vinylogous Acyl Triflates

  摘要：

  Reductive cyclization of aryl and vinyl iodides tethered to vinylogous acyl trifiates (VATS) induces a ring-expanding fragmentation to provide cyclic alkynyl ketones, including strained nine-membered cycloalkynes, in fair to excellent yield. The tandem cyclization/C-C bond-cleavage is Initiated under carefully optimized conditions by halogen metal exchange in the presence of carbonyl and vinyl triflate functionality. A modified protocol for alkylation of 1,3-cyclohexanedione is described for preparing the relevant VAT substrates.

  DOI：

  10.1021/ol2003308
• 作为产物：
  描述：

  2-碘苄醇 在 pyridinium chlorochromate 、 L-脯氨酸 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 2(2-iodobenzyl)cyclohexane-1,3-dione
  参考文献：
  名称：

  Generation of Medium-Ring Cycloalkynes by Ring Expansion of Vinylogous Acyl Triflates

  摘要：

  Reductive cyclization of aryl and vinyl iodides tethered to vinylogous acyl trifiates (VATS) induces a ring-expanding fragmentation to provide cyclic alkynyl ketones, including strained nine-membered cycloalkynes, in fair to excellent yield. The tandem cyclization/C-C bond-cleavage is Initiated under carefully optimized conditions by halogen metal exchange in the presence of carbonyl and vinyl triflate functionality. A modified protocol for alkylation of 1,3-cyclohexanedione is described for preparing the relevant VAT substrates.

  DOI：

  10.1021/ol2003308

文献信息

• Alkylation of Cyclic 1,3-Diketones
  作者：Thennati Rajamannar、Namasivayam Palani、Kalpattu Kuppuswamy Balasubramanian

  DOI：10.1080/00397919308011168

  日期：1993.12

  Abstract A simple procedure for the C-alkylation of cyclic 1,3-diketones have been reported using Triton B as base in aqueous conditions.

  摘要 已经报道了在水性条件下使用 Triton B 作为碱对环状 1,3-二酮进行 C-烷基化的简单程序。
• Synthesis of Wieland-Miescher Ketone Analogues-Potential Substrates for the Carbocyclic Frameworks
  作者：Rajamannar、Balasubramanian

  DOI：10.1080/00397919408011186

  日期：1994.2

  The synthesis of the hitherto unknown 3,4,8,8a-tetrahydro-8a(2-bromo-1-cyelo-alkenylmethyl)-1,6(2A,7A)-naphthalene- diones are reported.
• Generation of Medium-Ring Cycloalkynes by Ring Expansion of Vinylogous Acyl Triflates
  作者：Jumreang Tummatorn、Gregory B. Dudley

  DOI：10.1021/ol2003308

  日期：2011.3.18

  Reductive cyclization of aryl and vinyl iodides tethered to vinylogous acyl trifiates (VATS) induces a ring-expanding fragmentation to provide cyclic alkynyl ketones, including strained nine-membered cycloalkynes, in fair to excellent yield. The tandem cyclization/C-C bond-cleavage is Initiated under carefully optimized conditions by halogen metal exchange in the presence of carbonyl and vinyl triflate functionality. A modified protocol for alkylation of 1,3-cyclohexanedione is described for preparing the relevant VAT substrates.