Acetic acid (1R,4aS,8aS)-7-methoxy-8a-methyl-5,8-dioxo-1,4,4a,5,8,8a-hexahydro-naphthalen-1-yl ester | 300766-66-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Acetic acid (1R,4aS,8aS)-7-methoxy-8a-methyl-5,8-dioxo-1,4,4a,5,8,8a-hexahydro-naphthalen-1-yl ester
• 英文别名: [(1R,4aS,8aS)-7-methoxy-8a-methyl-5,8-dioxo-4,4a-dihydro-1H-naphthalen-1-yl] acetate
• CAS: 300766-66-9
• 化学式: C₁₄H₁₆O₅
• 分子量: 264.278
• InChiKey: ZZZHKIYFTBPCMV-IUPBHXKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Acetic acid (1R,4aS,8aS)-7-methoxy-8a-methyl-5,8-dioxo-1,4,4a,5,8,8a-hexahydro-naphthalen-1-yl ester 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 以99%的产率得到Acetic acid (1R,4aS,8R,8aR)-8-hydroxy-7-methoxy-8a-methyl-5-oxo-1,4,4a,5,8,8a-hexahydro-naphthalen-1-yl ester
  参考文献：
  名称：

  Enantio-face control by molecular sieves in the asymmetric Diels–Alder reaction

  摘要：

  The presence of molecular sieves 4 Angstrom (MS 4 Angstrom) significantly influenced enantioselectivity in the Diels-Alder reaction of 2-methoxy-5-methyl-1,4-benzoquinone with 1-acetoxy-1,3-butadiene promoted by chiral TADDOL-Ti complexes. In the absence of MS 4 Angstrom the (R)-adduct was formed in 72% ee, and in the presence of MS 4 Angstrom the (S)-enantiomer in up to 53% ee. Capture of HCl by MS 4 Angstrom has been demonstrated to play a critical role. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01116-3
• 作为产物：
  描述：

  1-acetoxybuta-1,3-diene 、 2-甲氧基-6-甲基对苯醌 在 titanium(IV) isopropylate 、 (4R,5R)-2,2-二甲基-a,a,a',a'-四苯基-1,3-二氧戊环-4,5-二甲醇 、 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以50%的产率得到Acetic acid (1R,4aS,8aS)-7-methoxy-8a-methyl-5,8-dioxo-1,4,4a,5,8,8a-hexahydro-naphthalen-1-yl ester
  参考文献：
  名称：

  Enantio-face control by molecular sieves in the asymmetric Diels–Alder reaction

  摘要：

  The presence of molecular sieves 4 Angstrom (MS 4 Angstrom) significantly influenced enantioselectivity in the Diels-Alder reaction of 2-methoxy-5-methyl-1,4-benzoquinone with 1-acetoxy-1,3-butadiene promoted by chiral TADDOL-Ti complexes. In the absence of MS 4 Angstrom the (R)-adduct was formed in 72% ee, and in the presence of MS 4 Angstrom the (S)-enantiomer in up to 53% ee. Capture of HCl by MS 4 Angstrom has been demonstrated to play a critical role. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01116-3