(S)-2-(5,5,5-trifluoro-4-(hydroxymethyl)pentyl)isoindoline-1,3-dione | 1180131-04-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: (S)-2-(5,5,5-trifluoro-4-(hydroxymethyl)pentyl)isoindoline-1,3-dione
• 英文别名: 2-[(4S)-5,5,5-trifluoro-4-(hydroxymethyl)pentyl]isoindole-1,3-dione
• CAS: 1180131-04-7
• 化学式: C₁₄H₁₄F₃NO₃
• 分子量: 301.265
• InChiKey: JYQFQGODTWBDHQ-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-2-(5,5,5-trifluoro-4-(hydroxymethyl)pentyl)isoindoline-1,3-dione 、 2-萘甲酰氯 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  The Productive Merger of Iodonium Salts and Organocatalysis: A Non-photolytic Approach to the Enantioselective α-Trifluoromethylation of Aldehydes

  摘要：

  An enantioselective organocatalytic alpha-trifluoromethylation of aldehydes has been accomplished using a commercially available, electrophilic trifluoromethyl source. The merging of Lewis acid and organocatalysis provides a new strategy for the enantioselective construction of trifluoromethyl stereogenicity, an important chiral synthon for pharmaceutical, materials, and agrochemical applications. This mild and operationally simple protocol allows rapid access to enantioenriched alpha-trifluoromethylated aldehydes through a nonphotolytic pathway.

  DOI：

  10.1021/ja100748y
• 作为产物：
  描述：

  (2S)-5-(1,3-dioxoisoindol-2-yl)-2-(trifluoromethyl)pentanal 在 sodium tetrahydroborate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 1.0h， 以0.186 g的产率得到(S)-2-(5,5,5-trifluoro-4-(hydroxymethyl)pentyl)isoindoline-1,3-dione
  参考文献：
  名称：

  Enantioselective α-Trifluoromethylation of Aldehydes via Photoredox Organocatalysis

  摘要：

  The first enantioselective, organocatalytic alpha-trifluoromethytation and alpha-perfluoroalkylation of aldehydes have been accomplished using a readily available iridium photocatalyst and a chiral imidazolidinone catalyst. A range of alpha-trifluoromethyl and alpha-perfluoroalkyl aldehydes were obtained from commercially available perfluoroalkyl halides with high efficiency and enantioselectivity. The resulting alpha-trifluoromethyl aldehydes were subsequently shown to be versatile precursors for the construction of a variety of enantioenriched trifluoromethylated building blocks.

  DOI：

  10.1021/ja9053338