(+/-)-β-conidendrin | 518-55-8

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 木脂素内酯
• 英文名称: (+/-)-β-conidendrin
• 英文别名: beta-Conidendrin；(3aS,9S,9aR)-7-hydroxy-9-(4-hydroxy-3-methoxyphenyl)-6-methoxy-3a,4,9,9a-tetrahydro-1H-benzo[f][2]benzofuran-3-one
• CAS: 518-55-8；5474-93-1；22614-13-7；26358-20-3；85699-62-3；89104-61-0；105817-20-7
• 化学式: C₂₀H₂₀O₆
• 分子量: 356.375
• InChiKey: CAYMSCGTKZIVTN-NJSLBKSFSA-N

物化性质

• 熔点：
  254-255 °C
• 沸点：
  601.4±55.0 °C(Predicted)
• 密度：
  1.334±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  85.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (+/-)-β-conidendrin 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 1,4-二氧六环 、 水 为溶剂， 以44%的产率得到detetrahydroconidendrin
  参考文献：
  名称：

  Directed, DDQ-Promoted Benzylic Oxygenations of Tetrahydronaphthalenes

  摘要：

  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.

  DOI：

  10.1021/jo981950u
• 作为产物：
  描述：

  4-(溴甲基)-2-甲氧基-1-苯基甲氧基苯 在 palladium on activated charcoal 六甲基磷酰三胺 、 sodium tetrahydroborate 、 三氟化硼乙醚 、 氢气 、 sodium methylate 、 三氟乙酸 、 mercury(II) oxide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， -80.0~25.0 ℃ 、399.99 kPa 条件下， 反应 87.5h， 生成 (+/-)-β-conidendrin
  参考文献：
  名称：

  练习曲：7-合成总的（±）-α等-β-分生孢子烯1个des的甲基（±）-α等-β-分生孢子

  摘要：

  将二噻吩的碳负离子迈克尔加成在丁烯内酯上，然后用苄基溴烷基化并酮酮羰基再生，得到α，β-二取代的内酯。使用NaBH 4还原后者的酮羰基羰基，然后用CF 3 CO 2 H处理并催化氢解得到（±）-α-分枝id烯。用DIBAL还原-二苄基（±）-α-分生烯醛，然后将中间乳醇甲基化并催化氢解，得到甲基1-表-（±）-α-分生烯醛。该化合物是Cambie描述为还具有结构的甲基α-二十二烯基差向异构体。

  DOI：

  10.1016/s0040-4020(01)87617-1

文献信息

• Syntheses of all eight stereoisomers of conidendrin
  作者：Hinako Shirakata、Hisashi Nishiwaki、Satoshi Yamauchi

  DOI：10.1080/09168451.2020.1777081

  日期：2020.10.2

  All eight stereoisomers of conidendrin were synthesized from (1 R,2 S,3 S)-1-(4-benzyloxy-3-methoxyphenyl)-3-(4-benzyloxy-3-methoxybenzyl)-2- hydroxymethyl-1,4-butanediol ((+)-4) and its enantiomer with high optical purity. The configurations at 4-positions of the conidendrin stereoisomers were constructed by intramolecular Friedel-Crafts reaction of protected 4. After conversion to tetrahydronaphthalene

  从（1 R，2  S，3  S）-1-（4-苄氧基-3-甲氧基苯基）-3-（4-苄氧基-3-甲氧基苄基）-2-羟甲基-1,4合成分生孢子蛋白的所有八个立体异构体 -具有高光学纯度的-丁二醇（（+）- 4）及其对映异构体。通过被保护的4的分子内Friedel-Crafts反应，构建了分生孢子蛋白立体异构体4位的构型。转化为四氢萘中间体7a后，将四氢萘结构7a的2-位和3-位分别转化为（+）-α-分枝烯苷（3a）的3a位和9a位。通过2a或3位7a的差向异构过程，获得了其他非对映异构体。所有对映体也由（-）- 4合成。
• Thermal process for beta conidendrin manufacture
  申请人：CROWN ZELLERBACH CORP

  公开号：US02610970A1

  公开（公告）日：1952-09-16
• Conidendrin. I. Its Isomerization and Demethylation¹
  作者：W. M. Hearon、Homer B. Lackey、Wendell W. Moyer

  DOI：10.1021/ja01152a131

  日期：1951.8
• 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.
• Etudes de lignanes
  作者：Robert Dhal、Yahia Nabi、Eric Brown

  DOI：10.1016/s0040-4020(01)87617-1

  日期：1986.1

  Michael addition of the carbanion of the dithian on butenolide, followed by alkylation with the benzylic bromide and regeneration of the ketonic carbonyl group, gave the α,β-disubstitued lactone . Reduction of the ketonic carbonyl of the latter using NaBH4, followed by treatment with CF3CO2H and catalytic hydrogenolysis afforded (±)-α-conidendrin . DIBAL reduction of -dibenzyl (±)-α-conidendrin and

  将二噻吩的碳负离子迈克尔加成在丁烯内酯上，然后用苄基溴烷基化并酮酮羰基再生，得到α，β-二取代的内酯。使用NaBH 4还原后者的酮羰基羰基，然后用CF 3 CO 2 H处理并催化氢解得到（±）-α-分枝id烯。用DIBAL还原-二苄基（±）-α-分生烯醛，然后将中间乳醇甲基化并催化氢解，得到甲基1-表-（±）-α-分生烯醛。该化合物是Cambie描述为还具有结构的甲基α-二十二烯基差向异构体。