(4aR,8aS)-1,4,4a,5,8,8a-Hexahydro-2-methoxy-8a-methyl-7-(1-methylethyl)-1,4-naphthalenedione | 145576-63-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4aR,8aS)-1,4,4a,5,8,8a-Hexahydro-2-methoxy-8a-methyl-7-(1-methylethyl)-1,4-naphthalenedione
• 英文别名: (4aR,8aS)-2-methoxy-8a-methyl-7-propan-2-yl-5,8-dihydro-4aH-naphthalene-1,4-dione
• CAS: 145576-63-2
• 化学式: C₁₅H₂₀O₃
• 分子量: 248.322
• InChiKey: FEWKGQSGEFEQSS-NHYWBVRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.67
• 重原子数：
  18.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  2-isopropyl-1,3-butadiene 、 2-甲氧基-6-甲基对苯醌 在 titanium(IV) isopropylate 、 chiral diol(+)-3 、 四氯化钛 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 生成 6-Isopropyl-2-methoxy-8a-methyl-4a,5,8,8a-tetrahydro-[1,4]naphthoquinone 、 (4aR,8aS)-1,4,4a,5,8,8a-Hexahydro-2-methoxy-8a-methyl-7-(1-methylethyl)-1,4-naphthalenedione 、 (4aS,8aR)-7-Isopropyl-2-methoxy-8a-methyl-4a,5,8,8a-tetrahydro-[1,4]naphthoquinone
  参考文献：
  名称：

  Assymetric quinone-based Deils-Alder reactions

  摘要：

  Asymmetric Diels-Alder reactions of 2-methoxy-1,4-benzoquinones utilizing a chiral Ti(IV) complex as a Lewis acid promoter are reported.

  DOI：

  10.1016/s0040-4039(00)61762-8

文献信息

• Formation and Isolation of Enantiomerically Pure Products in Quantity from Diels-Alder Reactions of 1,4-Benzoquinones
  作者：Thomas A. Engler、Michael A. Letavic、Kenneth O. Lynch、Fusao Takusagawa

  DOI：10.1021/jo00084a041

  日期：1994.3

  Diels-Alder reactions of 2-methoxy-6-methyl- and 2-methoxy-5-methyl-1,4-benzoquinones with various substituted dienes are promoted by a chiral complex prepared from TiCl4, Ti((OPr)-Pr-i)(4), and (2R,3R)-2,3-O-(1- phenylethylidene)-1,1,4,4-tetraphenyl-1,2,3,4-butanetetrol. The products from several dienes are formed in moderate to good ee and are obtained enantiomerically pure after simple recrystallization steps.