(4aR,8aS)-2-Methoxy-7,8a-dimethyl-4a,5,8,8a-tetrahydro-[1,4]naphthoquinone

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4aR,8aS)-2-Methoxy-7,8a-dimethyl-4a,5,8,8a-tetrahydro-[1,4]naphthoquinone
• 英文别名: (4aR,8aS)-2-methoxy-7,8a-dimethyl-5,8-dihydro-4aH-naphthalene-1,4-dione
• 化学式: C₁₃H₁₆O₃
• 分子量: 220.268
• InChiKey: OKNMBZHNQLZKAQ-ZANVPECISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4aR,8aS)-2-Methoxy-7,8a-dimethyl-4a,5,8,8a-tetrahydro-[1,4]naphthoquinone 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 0.08h， 以62%的产率得到(4aR,8aS)-2-Methoxy-7,8a-dimethyl-1,4,4a,5,8,8a-hexahydro-naphthalene-1,4-diol
  参考文献：
  名称：

  A New Approach to the Synthesis of Cortical Steroids

  摘要：

  AbstractA new bondset for cortical steroid synthesis is developed from the dual concepts of convergent assembly and multiple construction. A short synthesis on this bondset is presented in which the final bond construction by electrocyclization took an unwanted course. Stereocontrol is discussed separately.

  DOI：

  10.1002/jccs.199700022
• 作为产物：
  描述：

  3-甲氧基-5-甲基苯酚 在 potassium nitrososulfonate 、 四氯化钛 作用下， 以 丙酮 为溶剂， 反应 2.17h， 生成 (4aR,8aS)-2-Methoxy-7,8a-dimethyl-4a,5,8,8a-tetrahydro-[1,4]naphthoquinone
  参考文献：
  名称：

  A New Approach to the Synthesis of Cortical Steroids

  摘要：

  AbstractA new bondset for cortical steroid synthesis is developed from the dual concepts of convergent assembly and multiple construction. A short synthesis on this bondset is presented in which the final bond construction by electrocyclization took an unwanted course. Stereocontrol is discussed separately.

  DOI：

  10.1002/jccs.199700022

文献信息

• Catalysis and regioselectivity of quinone Diels–Alder reactions
  作者：James B. Hendrickson、Vishwakarma Singh

  DOI：10.1039/c39830000837

  日期：——

  In a series of six different cycloadditions of unsymmetrical quinones and alkyl-substituted butadienes, TiCl4 afforded considerable catalysis (–78 °C) and gave regioselectivity identical with that of the thermal reaction (200 °C) and therefore complementary to that BF3 catalysis.

  在一系列六种不对称醌和烷基取代的丁二烯的不同环加成反应中，TiCl 4具有相当的催化作用（–78°C），并具有与热反应（200°C）相同的区域选择性，因此可与BF 3催化作用互补。
• Assymetric quinone-based Deils-Alder reactions
  作者：Thomas A. Engler、Michael A. Letavic、Fusao Takusagawa

  DOI：10.1016/s0040-4039(00)61762-8

  日期：1992.11

  Asymmetric Diels-Alder reactions of 2-methoxy-1,4-benzoquinones utilizing a chiral Ti(IV) complex as a Lewis acid promoter are reported.
• 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.
• A New Approach to the Synthesis of Cortical Steroids
  作者：Ing-Lung Shih、James B. Hendrickson

  DOI：10.1002/jccs.199700022

  日期：1997.4

  AbstractA new bondset for cortical steroid synthesis is developed from the dual concepts of convergent assembly and multiple construction. A short synthesis on this bondset is presented in which the final bond construction by electrocyclization took an unwanted course. Stereocontrol is discussed separately.