2,2-dimethyl-5-(2'-carbethoxy-2'diphenylmethylimino-ethane)-1,3-dioxane | 133384-75-5

• 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-dimethyl-5-(2'-carbethoxy-2'diphenylmethylimino-ethane)-1,3-dioxane
• 英文别名: Ethyl 2-(benzhydrylideneamino)-3-(2,2-dimethyl-1,3-dioxan-5-yl)propanoate
• CAS: 133384-75-5
• 化学式: C₂₄H₂₉NO₄
• 分子量: 395.499
• InChiKey: YIVRTCDPQJEFFW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  57.1
• 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-(2'-carbethoxy-2'diphenylmethylimino-ethane)-1,3-dioxane 在 盐酸 作用下， 反应 4.0h， 以57%的产率得到5,5'-dihydroxyleucine
  参考文献：
  名称：

  Synthesis of 5,5′-dihydroxyleucine and 4-fluoro 5,5′-dihydroxyleucine, the reduction products of 4-carboxyglutamic and 4-carboxy-4-fluoroglutamic acids

  摘要：

  Schemes for the synthesis of 5-5'-dihydroxyleucine 3 and its 4-fluoro analog 7 involving the condensation of a suitable ''aminoacid moiety'' with 2,2-dimethyl-5-iodomethyl-1,3-dioxane 15D or its fluoro analog 27A were tested. The anion of the ethyl N-diphenylmethylene-glycinate 25 gave better yields of 3 than the classical anion of diethyl acetamidomalonate. This strategy could not be successfully applied to the synthesis of 7, which could be prepared by reduction of a suitably protected 4-fluoro-4-carboxyglutamate with BMS.

  DOI：

  10.1016/s0040-4020(01)80939-x
• 作为产物：
  描述：

  2,2-二甲基-[1,3]二恶烷-5,5-二甲酸二乙酯 在 lithium aluminium tetrahydride 、 四丁基碘化铵 、 三乙胺 、 sodium chloride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 、 乙醚 、 正己烷 、 水 、 二甲基亚砜 、 苯 为溶剂， 反应 14.5h， 生成 2,2-dimethyl-5-(2'-carbethoxy-2'diphenylmethylimino-ethane)-1,3-dioxane
  参考文献：
  名称：

  Synthesis of 5,5′-dihydroxyleucine and 4-fluoro 5,5′-dihydroxyleucine, the reduction products of 4-carboxyglutamic and 4-carboxy-4-fluoroglutamic acids

  摘要：

  Schemes for the synthesis of 5-5'-dihydroxyleucine 3 and its 4-fluoro analog 7 involving the condensation of a suitable ''aminoacid moiety'' with 2,2-dimethyl-5-iodomethyl-1,3-dioxane 15D or its fluoro analog 27A were tested. The anion of the ethyl N-diphenylmethylene-glycinate 25 gave better yields of 3 than the classical anion of diethyl acetamidomalonate. This strategy could not be successfully applied to the synthesis of 7, which could be prepared by reduction of a suitably protected 4-fluoro-4-carboxyglutamate with BMS.

  DOI：

  10.1016/s0040-4020(01)80939-x

文献信息

• Synthesis of 5,5′-dihydroxyleucine and 4-fluoro 5,5′-dihydroxyleucine, the reduction products of 4-carboxyglutamic and 4-carboxy-4-fluoroglutamic acids
  作者：Joëlle Dubois、Christine Fourès、Sonia Bory、Serge Falcou、Michel Gaudry、Andrée Marquet

  DOI：10.1016/s0040-4020(01)80939-x

  日期：1991.1

  Schemes for the synthesis of 5-5'-dihydroxyleucine 3 and its 4-fluoro analog 7 involving the condensation of a suitable ''aminoacid moiety'' with 2,2-dimethyl-5-iodomethyl-1,3-dioxane 15D or its fluoro analog 27A were tested. The anion of the ethyl N-diphenylmethylene-glycinate 25 gave better yields of 3 than the classical anion of diethyl acetamidomalonate. This strategy could not be successfully applied to the synthesis of 7, which could be prepared by reduction of a suitably protected 4-fluoro-4-carboxyglutamate with BMS.