trans-2-(3''-hydroxy-4''-methoxybenzyl)-3-(3',4'-dimethoxybenzyl)butyrolactone | 87605-56-9

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 呋喃类木脂素
• 英文名称: trans-2-(3''-hydroxy-4''-methoxybenzyl)-3-(3',4'-dimethoxybenzyl)butyrolactone
• 英文别名: (+/-)-prestegane A
• CAS: 87605-56-9；87678-76-0
• 化学式: C₂₁H₂₄O₆
• 分子量: 372.418
• InChiKey: TUXIKUQNFFNQOA-CVEARBPZSA-N

物化性质

• 沸点：
  568.6±45.0 °C(Predicted)
• 密度：
  1.227±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.99
• 重原子数：
  27.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  74.22
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  trans-2-(3''-hydroxy-4''-methoxybenzyl)-3-(3',4'-dimethoxybenzyl)butyrolactone 在 盐酸 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 72.0h， 生成 2-(3-hydroxy-4-methoxybenzyl)-3-(3,4-dimethoxybenzyl)tetrahydrofuran
  参考文献：
  名称：

  Oxidative cyclisation of 3,4-dibenzyltetrahydrofurans using ruthenium tetra(trifluoroacetate)

  摘要：

  A series of trans-3,4-dibenzyltetrahydrofurans has been synthesised and subjected to oxidative cyclisation using ruthenium tetra(trifluoroacetate), affording dibenzocyclooctadiene lignans belonging to the isostegane series, in high yields. Since no evidence was found for the formation of the corresponding stegane isomers it is assumed that the reactions proceed with complete diastereoselectivity. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00025-4
• 作为产物：
  描述：

  trans-2-(3''-benzyloxy-4''-methoxybenzyl)-3-(3',4'-dimethoxy-α,α-bisbenzyl)butyrolactone 在 sodium tetrahydroborate 、 nickel dichloride 作用下， 生成 trans-2-(3''-hydroxy-4''-methoxybenzyl)-3-(3',4'-dimethoxybenzyl)butyrolactone
  参考文献：
  名称：

  酚二苄基丁内酯的高价碘氧化制备四氢二苯并环辛烯木脂素和螺二烯酮。

  摘要：

  根据在反应中允许的时间长度，在三氟乙醇中用Phl（OCOCF 3）2处理二苄基丁内酯18，主要产物为螺二烯酮28或四氢二苯并环辛烯29。第二dibenzylbutyrolactone的反应19相同的条件下给出的产品33，34，36和38，而20给出了43直接。这些反应提供了螺二烯酮如28和33的第一批合成物，被假定为四氢二苯并环辛烯木脂素生物合成的中间体。

  DOI：

  10.1016/0040-4020(95)00960-4

文献信息

• New agents of biaryl oxidative coupling in fluoro acid medium. VI. Application to the synthesis of phenolic bisbenzocyclooctadiene lignans
  作者：Denis Planchenault、Robert Dhal、Jean-Pierre Robin

  DOI：10.1016/0040-4020(94)01028-x

  日期：1995.1

  carried out for the oxidative coupling of bisbenzocyclooctadiene lignan precursors. Tl2O3 and Re2O7 were found to be the more efficient reagents with precursors possessing methylenedioxy substituents for the former and only methoxy groups for the latter. Finally, oxidative coupling of a phenolic dibenzylbutane led to a mixture of two BBCOD's, resulting from para and ortho coupling to the phenolic group

  对于双苯并环辛二烯木脂素前体的氧化偶联，已经进行了对氟酸介质中氧化还原对的系统研究。发现Tl 2 O 3和Re 2 O 7是更有效的试剂，其前体具有前者具有亚甲基二氧基取代基，而后者仅具有甲氧基。最终，酚对二苄基丁烷的氧化偶合导致两个BBCOD的混合物，这是由于对酚基的对位和邻位偶合。
• Oxidative cyclisation of cis- and trans-2,3-dibenzylbutyrolactones using ruthenium tetra(trifluoroacetate)
  作者：Robert S Ward、David D Hughes

  DOI：10.1016/s0040-4020(01)00273-3

  日期：2001.4

  A series of cis- and trans-2,3-dibenzylbutyrolactones have been synthesised and subjected to oxidative cyclisation using ruthenium tetra(trifluoroacetate) affording dibenzocyclooctadiene lactones belonging to the stegane and isostegane series of lignans.

  已经合成了一系列顺式和反式-2,3-二苄基丁内酯，并使用四（三氟乙酸）钌进行氧化环化，得到属于木脂烷和异庚烷系列的二苯并环辛二烯内酯。
• Oxidative cyclisation of cis- and trans-2,3-dibenzylbutyrolactones using phenyl iodonium bis(trifluoroacetate) and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone
  作者：Robert S Ward、David D Hughes

  DOI：10.1016/s0040-4020(01)00472-0

  日期：2001.6

  A series of cis- and trans-2,3-dibenzylbutyrolactones have been subjected to oxidative cyclisation using phenyl iodonium bis(trifluoroacetate) and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone. The products obtained include two novel spirodienones 6 and 11, which rearrange with acid to give the dibenzocyclo-octadienes 7, and 12 and 13, respectively.

  使用苯基碘双（三氟乙酸酯）和2,3-二氯-5,6-二氰基-1,4-苯醌，对一系列顺式和反式-2,3-二苄基丁内酯进行了氧化环化反应。获得的产品包括两个新的spirodienones 6和11，其与酸重新排列，得到dibenzocyclo-辛二烯7，和12和13，分别。
• Ruthenium dioxide in fluoro acid medium: II. Application to the formation of steganes skeleton by oxidative phenolic coupling.
  作者：Jean-Pierre Robin、Yannick Landais

  DOI：10.1016/s0040-4020(01)88186-2

  日期：——

  Ruthenium (IV) dioxide dihydrate in fluoro acidic medium was found to be a very efficient agent for the oxidative coupling of the phenolic lignans (+/-)-presteganes A and B. Different attempts to oxidise the diphenolic dibenzylbutanolide (+/-)-HPMF were also carried out, but were unsuccessful. Likely explanation for these failures are given.
• Ruthenium(IV) dioxide in fluoro acid medium. An efficient biaryl phenol coupling process, exemplified with a biomimetic access to the skeleton of steganacin from presteganes
  作者：Jean Pierre Robin、Yannick Landais

  DOI：10.1021/jo00236a056

  日期：1988.1