(3R,1'R)-5-hydroxy-3-methylpentanoic acid (1'-α-naphthyl)ethyl ester | 214260-94-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (3R,1'R)-5-hydroxy-3-methylpentanoic acid (1'-α-naphthyl)ethyl ester
• 英文别名: [(1R)-1-naphthalen-1-ylethyl] (3R)-5-hydroxy-3-methylpentanoate
• CAS: 214260-94-3
• 化学式: C₁₈H₂₂O₃
• 分子量: 286.371
• InChiKey: PTEFJEPMOVBRPQ-ZIAGYGMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3R,1'R)-5-hydroxy-3-methylpentanoic acid (1'-α-naphthyl)ethyl ester 在 4-甲基苯磺酸吡啶 、 二异丁基氢化铝 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 12.5h， 生成 (3R,2''RS)-3-methyl-5-(2-tetrahydropyranyloxy)pentanal
  参考文献：
  名称：

  Oxazoline N-Oxide-Mediated [2 + 3] Cycloadditions: Application to a Total Synthesis of the Hypocholesterolemic Agent 1233A

  摘要：

  Oxetanone 1233A1 has been synthesized in 22 steps and 3.43% overall yield from 3-methylglutaric anhydride. Asymmetric carbon at C-7 was introduced by a diastereoselective esterification of 3-methylglutaric anhydride, whereas the two asymmetric carbons at C-2' and C-3' were controlled by an asymmetric [2 +/- 3] cycloaddition using camphor-derived oxazoline N-oxide as dipole.

  DOI：

  10.1021/jo980813u
• 作为产物：
  描述：

  (3R)-3-methyl-5-[(1R)-1-naphthalen-1-ylethoxy]-5-oxopentanoic acid 在 dimethyl sulfide borane 作用下， 以 四氢呋喃 为溶剂， 以97%的产率得到(3R,1'R)-5-hydroxy-3-methylpentanoic acid (1'-α-naphthyl)ethyl ester
  参考文献：
  名称：

  Oxazoline N-Oxide-Mediated [2 + 3] Cycloadditions: Application to a Total Synthesis of the Hypocholesterolemic Agent 1233A

  摘要：

  Oxetanone 1233A1 has been synthesized in 22 steps and 3.43% overall yield from 3-methylglutaric anhydride. Asymmetric carbon at C-7 was introduced by a diastereoselective esterification of 3-methylglutaric anhydride, whereas the two asymmetric carbons at C-2' and C-3' were controlled by an asymmetric [2 +/- 3] cycloaddition using camphor-derived oxazoline N-oxide as dipole.

  DOI：

  10.1021/jo980813u

文献信息

• Oxazoline <i>N</i>-Oxide-Mediated [2 + 3] Cycloadditions: Application to a Total Synthesis of the Hypocholesterolemic Agent 1233A
  作者：Olivier Dirat、Cyrille Kouklovsky、Yves Langlois

  DOI：10.1021/jo980813u

  日期：1998.9.1

  Oxetanone 1233A1 has been synthesized in 22 steps and 3.43% overall yield from 3-methylglutaric anhydride. Asymmetric carbon at C-7 was introduced by a diastereoselective esterification of 3-methylglutaric anhydride, whereas the two asymmetric carbons at C-2' and C-3' were controlled by an asymmetric [2 +/- 3] cycloaddition using camphor-derived oxazoline N-oxide as dipole.