(4S)-4-(tert-butyldimethylsiloxy)-2-phenylselenyloctylnitrile | 1039034-42-8

• 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: (4S)-4-(tert-butyldimethylsiloxy)-2-phenylselenyloctylnitrile
• 英文别名: (4S)-4-[tert-butyl(dimethyl)silyl]oxy-2-phenylselanyloctanenitrile
• CAS: 1039034-42-8
• 化学式: C₂₀H₃₃NOSeSi
• 分子量: 410.534
• InChiKey: JYJKTVLSFBVNGX-KKFHFHRHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  24
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  33
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (4S)-4-(tert-butyldimethylsiloxy)-2-phenylselenyloctylnitrile 在 双氧水 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 7.5h， 生成 (S)-4-(tert-butyldimethylsiloxy)-2-octenylnitrile 、 (S)-4-(tert-butyldimethylsiloxy)-2-octenylnitrile
  参考文献：
  名称：

  Asymmetric Total Synthesis of Botcinins C, D, and F

  摘要：

  Stereoselective total synthesis of botcinins C, D, and F is effectively carried out through asymmetric aldol reactions, 6-endo ring closure, and Sml(12)-mediated 3,4-trans or -cis stereoselective intramolecular Reformatsky reaction. Rapid esterification of the main skeleton of botcinins with the chiral side chain using MNBA and DMAP produced botcinin D, an antifungal chemical against a pathogen of rice blast disease.

  DOI：

  10.1021/ol801066y
• 作为产物：
  描述：

  (4S)-4-(tert-butyldimethylsiloxy)-2-(methanesulfonyloxy)octylnitrile 、 苯硒酚 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以95%的产率得到(4S)-4-(tert-butyldimethylsiloxy)-2-phenylselenyloctylnitrile
  参考文献：
  名称：

  Asymmetric Total Synthesis of Botcinins C, D, and F

  摘要：

  Stereoselective total synthesis of botcinins C, D, and F is effectively carried out through asymmetric aldol reactions, 6-endo ring closure, and Sml(12)-mediated 3,4-trans or -cis stereoselective intramolecular Reformatsky reaction. Rapid esterification of the main skeleton of botcinins with the chiral side chain using MNBA and DMAP produced botcinin D, an antifungal chemical against a pathogen of rice blast disease.

  DOI：

  10.1021/ol801066y

文献信息

• Asymmetric Total Synthesis of Botcinins C, D, and F
  作者：Hiroki Fukui、Isamu Shiina

  DOI：10.1021/ol801066y

  日期：2008.7.17

  Stereoselective total synthesis of botcinins C, D, and F is effectively carried out through asymmetric aldol reactions, 6-endo ring closure, and Sml(12)-mediated 3,4-trans or -cis stereoselective intramolecular Reformatsky reaction. Rapid esterification of the main skeleton of botcinins with the chiral side chain using MNBA and DMAP produced botcinin D, an antifungal chemical against a pathogen of rice blast disease.