β-conidendreol dimethyl ether | 66510-81-4

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 芳基四氢萘木脂素
• 英文名称: β-conidendreol dimethyl ether
• 英文别名: (+)-dimethyl-β-conidendryl alcohol；(1S)-1r-(3,4-dimethoxy-phenyl)-2t,3t-bis-hydroxymethyl-6,7-dimethoxy-1,2,3,4-tetrahydro-naphthalene；(1S)-1r-(3,4-Dimethoxy-phenyl)-2t,3t-bis-hydroxymethyl-6,7-dimethoxy-1,2,3,4-tetrahydro-naphthalin；[(2S,3R,4S)-4-(3,4-dimethoxyphenyl)-3-(hydroxymethyl)-6,7-dimethoxy-1,2,3,4-tetrahydronaphthalen-2-yl]methanol
• CAS: 66510-81-4
• 化学式: C₂₂H₂₈O₆
• 分子量: 388.461
• InChiKey: LTMZRNBMJLXRNY-ZWWNWMABSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  77.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  β-conidendreol dimethyl ether 在 potassium hydrogensulfate 作用下， 生成 anhydro-β-conidendreol dimethyl ether
  参考文献：
  名称：

  Conidendrin. II.¹ The Stereochemistry and Reactions of the Lactone Ring²

  摘要：

  DOI：

  10.1021/ja01649a021
• 作为产物：
  描述：

  β-conidendrin dimethyl ether 在 四氢呋喃 、 lithium aluminium tetrahydride 作用下， 生成 β-conidendreol dimethyl ether
  参考文献：
  名称：

  Application of Tosylate Reductions and Molecular Rotations to the Stereochemistry of Lignans²

  摘要：

  DOI：

  10.1021/ja01607a063

文献信息

• Concerning phyltetralin
  作者：Robert Stevenson、John R. Williams

  DOI：10.1016/0040-4020(77)88022-8

  日期：1977.1

  The acid-catalyzed rearrangement of diaryl-dilactones, readily obtained by oxidation of ferulic acid derivatives, is examined as a synthesis route to aryltetralins. Two structures which have been proposed for the lignan, phyltetralin, are shown by synthesis of the two diastereomeric 1-veratryltetralins (3A) and (3B), to be untenable. Conidendrin has been converted to isolariciresinol tetramethyl ether

  容易通过阿魏酸衍生物的氧化获得的酸催化的二芳基-二内酯重排作为合成芳基四氢萘的合成途径得到了检验。通过合成两个非对映异构的1-veratryltetralins（3A）和（3B），显示了针对木脂素phyltetralin提出的两个结构是站不住脚的。分生孢子素已被转化为异二十碳烯醇四甲醚（21），经验常数和光谱与叶绿素的报道进行比较，强烈表明木脂素具有对映体组成（26）。
• Directed, DDQ-Promoted Benzylic Oxygenations of Tetrahydronaphthalenes
  作者：Frank D. Ramdayal、David J. Kiemle、Robert T. LaLonde

  DOI：10.1021/jo981950u

  日期：1999.6.1

  Positional preferences for-para benzylic oxygenation of tetrahydronaphthalenes by 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ)-aqueous dioxane were investigated by comparing the tetralone products from 6-hydroxy-7-methoxy- and 6-acetoxy-7-methoxy-1,2,3,4-tetrahydronaphthalene. The directing influence by an aromatic substituent on para benzylic oxygenation was in the order OH > OMe > OAc. Consistent with this finding were results obtained from lignan analogues. Treatment of (+)-beta-conidendryl alcohol with DDQ in dry dioxane resulted in the intramolecular bridging by one of two primary hydroxy groups to the benzylic position, giving an oxabicyclo[3.2.1]octane. Similar treatment of (+)-dimethyl-beta-conidendryl alcohol resulted in bridging by the alternate primary hydroxyl group to the benzhydrylic carbon giving an isomeric oxabicyclo[3.2.1]octane.
• Carnmalm, Acta Chemica Scandinavica (1947-1973), 1954, vol. 8, p. 1827
  作者：Carnmalm

  DOI：——

  日期：——
• Carnmalm, Acta Chemica Scandinavica (1947-1973), 1954, vol. 8, p. 806,809
  作者：Carnmalm

  DOI：——

  日期：——
• Application of Tosylate Reductions and Molecular Rotations to the Stereochemistry of Lignans²
  作者：Anthony W. Schrecker、Jonathan L. Hartwell

  DOI：10.1021/ja01607a063

  日期：1955.1