(R)-2-chloro-4-(1,5,5-trimethylhydantyl)butanoic acid pentachlorophenyl ester | 860803-14-1

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: (R)-2-chloro-4-(1,5,5-trimethylhydantyl)butanoic acid pentachlorophenyl ester
• 英文别名: (2,3,4,5,6-pentachlorophenyl) (2R)-2-chloro-4-(3,4,4-trimethyl-2,5-dioxoimidazolidin-1-yl)butanoate
• CAS: 860803-14-1
• 化学式: C₁₆H₁₄Cl₆N₂O₄
• 分子量: 511.016
• InChiKey: PDMRHGVLLXUARY-ZCFIWIBFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  66.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-2-chloro-4-(1,5,5-trimethylhydantyl)butanoic acid pentachlorophenyl ester 在 Amberlite hydrogen sulfide resin 、 Celite 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 15.0h， 生成 (2S)-3,3-二甲基-2-甲基氨基-N-[(2S)-4-甲基-2-[[(2S)-2-硫基-4-(3,4,4-三甲基-2,5-二氧代-咪唑烷-1-基)丁酰基]氨基]戊酰]丁酰胺
  参考文献：
  名称：

  Performing the Synthesis of a Complex Molecule on Sequentially Linked Columns:  Toward the Development of a “Synthesis Machine”

  摘要：

  We describe the diastereoselective synthesis of a pharmaceutically active drug candidate via a column-based system. This methodology is complementary to classical solid-phase synthesis; individual columns are packed with resin-bound reagents and then linked in sequence and/or in parallel. In contrast to the traditional solid-phase approach, substrates are introduced in the mobile phase where they build up chemical complexity by percolating through the linked columns, ultimately eluting as the desired product.

  DOI：

  10.1021/ol050980y
• 作为产物：
  描述：

  4-(1,5,5-trimethylhydantyl)butanoyl chloride 、 2,3,4,5,6,6-六氯-2,4-环己二烯-1-酮 在 benzoylquinine-loaded Wang resin VHL 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 (S)-2-chloro-4-(1,5,5-trimethylhydantyl)butanoic acid pentachlorophenyl ester 、 (R)-2-chloro-4-(1,5,5-trimethylhydantyl)butanoic acid pentachlorophenyl ester
  参考文献：
  名称：

  A column-based ‘flush and flow’ system for the asymmetric α-chlorination of acid halides

  摘要：

  We describe a column based flow system in which a cinchona alkaloid based reagent/catalyst solid-phase promotes the asymmetric a-chlorination of acid chlorides to afford highly optically active alpha-chloroesters in high enantiomeric excess and in good yields. (c) 2005 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetasy.2005.09.014