2,2-dimethyl-5-(5-chloropentanoyl)-1,3-dioxan-4,6-dione | 882872-52-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,2-dimethyl-5-(5-chloropentanoyl)-1,3-dioxan-4,6-dione
• 英文别名: 5-(5-Chloropentanoyl)-2,2-dimethyl-1,3-dioxane-4,6-dione
• CAS: 882872-52-8
• 化学式: C₁₁H₁₅ClO₅
• 分子量: 262.69
• InChiKey: DQWBDBKNMUZKBI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,2-dimethyl-5-(5-chloropentanoyl)-1,3-dioxan-4,6-dione 在 potassium tert-butylate 、 四丁基碘化铵 、 对甲苯磺酸 作用下， 以 乙二醇二甲醚 、 甲苯 为溶剂， 反应 2.0h， 生成 1-[(1S)-phenylethyl]-2-[(methoxycarbonyl)methyliden]piperidine
  参考文献：
  名称：

  Practical method for the synthesis of (R)-homopipecolinic acid and (R)-homoproline esters from ω-chloroalkanoic acids and available chiral amines

  摘要：

  A practical synthesis of (R)-homopipecolinic acid methyl ester 1 and (R)-homoproline methyl ester 2 was performed utilizing (i) a direct intramolecular cyclization of omega-chloro-beta-enamino esters 11 and 12, which were prepared from available (S)-1-phenylethylamine or (S)-1-(1-naphthyl)ethylamine and omega-chloro-beta-keto esters 5 and 10, respectively and (ii) a highly diastereoselective NaBH4 reduction followed by hydrogenolysis. The present method is a short-step process using inexpensive and readily available substrates and reagents with fewer wasted materials. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.12.014
• 作为产物：
  描述：

  丙二酸环(亚)异丙酯 、 5-氯戊酸 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以95%的产率得到2,2-dimethyl-5-(5-chloropentanoyl)-1,3-dioxan-4,6-dione
  参考文献：
  名称：

  Practical method for the synthesis of (R)-homopipecolinic acid and (R)-homoproline esters from ω-chloroalkanoic acids and available chiral amines

  摘要：

  A practical synthesis of (R)-homopipecolinic acid methyl ester 1 and (R)-homoproline methyl ester 2 was performed utilizing (i) a direct intramolecular cyclization of omega-chloro-beta-enamino esters 11 and 12, which were prepared from available (S)-1-phenylethylamine or (S)-1-(1-naphthyl)ethylamine and omega-chloro-beta-keto esters 5 and 10, respectively and (ii) a highly diastereoselective NaBH4 reduction followed by hydrogenolysis. The present method is a short-step process using inexpensive and readily available substrates and reagents with fewer wasted materials. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.12.014