(3S,4R,5S)-4-(dimethylphenylsilyl)-4,5-dihydro-5-methyl-3-(5-methylhexyl)-2(3H)-furanone | 214210-37-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (3S,4R,5S)-4-(dimethylphenylsilyl)-4,5-dihydro-5-methyl-3-(5-methylhexyl)-2(3H)-furanone
• 英文别名: (3S,4R,5S)-4-[dimethyl(phenyl)silyl]-5-methyl-3-(5-methylhexyl)oxolan-2-one
• CAS: 214210-37-4
• 化学式: C₂₀H₃₂O₂Si
• 分子量: 332.558
• InChiKey: YYSJFJMGSFSEPT-UHOSZYNNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.75
• 重原子数：
  23.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (3S,4R,5S)-4-(dimethylphenylsilyl)-4,5-dihydro-5-methyl-3-(5-methylhexyl)-2(3H)-furanone 在 过氧乙酸 、 sodium acetate 、 potassium bromide 作用下， 以 溶剂黄146 为溶剂， 反应 21.0h， 以63%的产率得到(-)-NFX-4
  参考文献：
  名称：

  Brief syntheses of (+)-blastmycinone and related γ-lactones from an asymmetrically dihydroxylated carboxylic ester

  摘要：

  A method for synthesizing optically active trans,trans-configurated alpha,beta,gamma-substituted gamma-lactones is presented. Asymmetric hydroxylation of ester 8 with AD mix alpha (AD mix beta) and subsequent dehydration provided butenolide S-6 (R-6). Conjugate addition of Li-2(Me2PhSi)(2)Cu(CN) to S-6 followed by alkylation of the resulting enolate led to the stereopure silyllactones 9-11. They furnished the title compounds after oxidative removal of the Me2PhSi group. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00687-5
• 作为产物：
  描述：

  5-甲基-1-己醇 在 咪唑 、 碘 、 三苯基膦 作用下， 以 乙醚 、 乙腈 为溶剂， 反应 0.5h， 生成 (3S,4R,5S)-4-(dimethylphenylsilyl)-4,5-dihydro-5-methyl-3-(5-methylhexyl)-2(3H)-furanone
  参考文献：
  名称：

  Brief syntheses of (+)-blastmycinone and related γ-lactones from an asymmetrically dihydroxylated carboxylic ester

  摘要：

  A method for synthesizing optically active trans,trans-configurated alpha,beta,gamma-substituted gamma-lactones is presented. Asymmetric hydroxylation of ester 8 with AD mix alpha (AD mix beta) and subsequent dehydration provided butenolide S-6 (R-6). Conjugate addition of Li-2(Me2PhSi)(2)Cu(CN) to S-6 followed by alkylation of the resulting enolate led to the stereopure silyllactones 9-11. They furnished the title compounds after oxidative removal of the Me2PhSi group. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00687-5