1,3-dihydroxy-5-<14'-(3'',5''-dihydroxyphenyl)tetradecyl>benzene | 26050-60-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 1,3-dihydroxy-5-<14'-(3'',5''-dihydroxyphenyl)tetradecyl>benzene
• 英文别名: 1,3-dihydroxy-5-[14''-(1',3'-dihydroxyphenyl)tetradecyl]benzene；bis-norstriatol；1,14-Bis-(3,5-dihydroxyphenyl)-tetradecan；Bisnorstriatol；5-[14-(3,5-dihydroxyphenyl)tetradecyl]benzene-1,3-diol
• CAS: 26050-60-2
• 化学式: C₂₆H₃₈O₄
• 分子量: 414.585
• InChiKey: QUXULJDSRDXUCR-UHFFFAOYSA-N

物化性质

• 熔点：
  138 °C (decomp)
• 沸点：
  602.6±30.0 °C(Predicted)
• 密度：
  1.106±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.2
• 重原子数：
  30
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  80.9
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,3-dihydroxy-5-<14'-(3'',5''-dihydroxyphenyl)tetradecyl>benzene 、 硫酸二甲酯 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 生成 1,3-dimethoxy-5-<14'-(3'',5''-dimethoxyphenyl)tetradecyl>benzene
  参考文献：
  名称：

  New phenolic constituents or Grevillea robusta wood

  摘要：

  DOI：

  10.1016/s0031-9422(00)97132-2
• 作为产物：
  描述：

  5-(5'-bromopentyl)-1,3-dimethoxybenzene 在 palladium on activated charcoal 六甲基磷酰三胺 、 甲基碘化镁 、 正丁基锂 、 氢气 作用下， 以 二甲基亚砜 为溶剂， 反应 25.0h， 生成 1,3-dihydroxy-5-<14'-(3'',5''-dihydroxyphenyl)tetradecyl>benzene
  参考文献：
  名称：

  5-Alkylresorcinols from Hakea trifurcata, that cleave DNA.

  摘要：

  A dichloromethane extract of Hakea trifurcata that mediated relaxation of phi X174 replicative form DNA at micromolar concentrations in the presence of CU2+ was resolved into six active components by bioassay-guided fractionation. Five of the active principles were characterized structurally and shown to be 5-alkylresorcinol derivatives. These included 1,3-dihydroxy-5-tridecylbenzene (1), 1,3-dihydroxy-5-(cis-8'-pentadecenyl)benzene (2), 1,3-dihydroxy-5-[14'-(3'',5''-dihydroxyphenyl)-cis-6'-tetradecenyl]benzene (3), 1,3-dihyroxy-5-[1 4'-(3'',5''-dihydroxyphenyl)tetradecyl]benzene (4), and 1,3-dihydroxy-5-[16'-(3'',5''-dihydroxyphenyl)-cis-8'-hexadencenyl]benzene (5). The structures of these five natural principles were confirmed by total synthesis; compounds 1-5 were accessible from 3,5-dimethoxybenzaldehyde in overall yields of 59%, 27%, 15%, 16%, and 13%, respectively.

  DOI：

  10.1021/ja00156a004

文献信息

• Shortcut Syntheses of Naturally Occurring 5-Alkylresorcinols with DNA-Cleaving Properties
  作者：Alois Fürstner、Günter Seidel

  DOI：10.1021/jo962423i

  日期：1997.4.1

  stereoselective manner, the remaining two terminal alkylboranes are treated with NaOMe, and the bis-borate complex 13 thus formed is finally used as the nucleophile for a palladium-catalyzed Suzuki cross-coupling reaction with triflate 7. This sequence is carried out in one pot and provides product 14 in 62% overall yield. Demethylation of 14 (and analogues) can be conveniently achieved by means of 9-iodo-9-BBN

  最近已从天然来源中分离出间苯二酚，例如在C-5位置带有长烷基或烯基取代基的1-5，包括硼酸酯形式的双间苯二酚衍生物，并显示出在氧化条件下具有出色的DNA裂解特性。就其结构简单而言，先前合成此类化合物的合成方法似乎冗长。公开了一种非常灵活的合成，其通过硼介导的反应歧管分别从三氟甲磺酸酯7和易于获得的烯烃，二烯，烯或二烯组装这些靶。作为一个典型的例子，在所有可能的位置上，用9-H-9-BBN对十六烷基-1,15-dien-8-yne 11进行氢硼化，将生成的三硼烷12的烯基硼烷实体选择性地裂解掉，得到以立体选择性的方式得到所需的（Z）-烯基，剩余的两个末端烷基硼烷用NaOMe处理，最终形成的双硼酸酯络合物13用作亲核试剂，用于钯催化的与三氟甲磺酸酯7的Suzuki交叉偶联反应。该步骤在一个罐中进行，提供了产物14％的总产率为14。可以通过9-碘-9-BBN方便地实现14（及其类似物）的去甲基化
• [EN] USE OF NATURAL PRODUCTS AND RELATED SYNTHETIC COMPOUNDS FOR THE TREATMENT OF CARDIOVASCULAR DISEASE<br/>[FR] UTILISATION DE PRODUITS NATURELS ET DE COMPOSES SYNTHETIQUES APPARENTES POUR LE TRAITEMENT DE MALADIES CARDIO-VASCULAIRES
  申请人：THE UNIVERSITY OF SYDNEY

  公开号：WO1994028886A1

  公开（公告）日：1994-12-22

  (EN) Use of a compound of formula (I), wherein Ar is an aromatic ring system comprising one or more optionally substituted phenyl rings optionally linked to or fused with one or more other optionally substituted phenyl rings or one or more 5 or 6-membered, optionally substituted heterocyclic rings wherein the heteroatom is oxygen; and wherein the ring system comprises 1-4 phenyl rings and wherein Ar can be linked to another Ar via a group X wherein the Ar is independently selected; where X is optionally substituted C1-20alkylene, C2-20alkenylene or C2-20alkynylene; R is hydrogen; C1-20alkenyl, C2-20alkynyl, C2-20alkanoyl, C2-20alkynoyl, each of which can be optionally substituted; R1 is independently selected and is hydrogen; optionally substituted C1-12alkyl, C2-12alkenyl, C2-12alkynyl; -COOR' -NR'R', halogen, -OR', -COR', -CONR'R', =O, -SR', -SO3R', -SO2NR'R', -SOR', -SO2R', -NO2, -CN, glycoside, silyl; where R' is independently hyrogen; alkyl, alkenyl or alkynyl each optionally substituted; and where two groups R1 can be joined; wherein the optional substituents are one or more independently selected from C1-10alkyl, C2-10alkenyl, C2-10alkynyl; -COOR' -NR'R', halogen, OR', -COR', -CONR'R', -SR', =O, -SO3R', -SO2NR'R', -SOR', -SO2', -NO2, -CN; wherein R' is independently hydrogen, alkyl, alkenyl, or alkynyl; n = 1, 2 or 3; m = 1, 2, 3 or 4; or a pharmaceutically acceptable derivative thereof in the manufacture of a medicament for inhibiting the action of Ca2+-ATPase enzymes. Certain compounds of formula (I) and 8-lavandulyl flavone pharmaceutical formulations are new.(FR) L'invention concerne l'utilisation d'un composé selon la formule (I) où Ar représente un système de cycles aromatiques comprenant un ou plusieurs cycles phényle éventuellement substitués, optionnellement reliés ou fusionnés avec un ou plusieurs autres cycles phényle optionnellement substitués ou un ou plusieurs cycles hétérocycliques optionnellement substitués, à 5 ou 6 éléments, dans lesquels l'hétéroatome est de l'oxygène; et où le système de cycles comprend 1 à 4 cycles phényle et où Ar peut être lié à un autre Ar via un groupe X dans lequel Ar est choisi indépendamment; où X est alkylène C1-20, alcénylène C2-20 ou alcynylène C2-20 optionnellement substitué; R représente hydrogène, alcényle C1-20, alcynyle C2-20, alcanoyle C2-20, alcynoyle C2-20, chacun pouvant être optionnellement substitué; R1 est choisi indépendamment et représente hydrogène, alkyle C1-12, alcényle C2-12, alcynyle C2-12 optionnellement substitué; -COOR' -NR'R', halogène, -OR', -COR', -CONR'R', =O, -SR', -SO3R', -SO2NR'R', -SOR', -SO2R', -NO2, -CN, glycoside, silyle; où R' représente indépendamment hydrogène, alkyle, alcényle ou alcynyle, chacun étant optionnellement substitué; et où deux groupes R1 peuvent être reliés; où les substituants optionnels sont un ou plusieurs éléments indépendamment sélectionnés parmi alkyle C1-10, alcényle C2-10, alcynyle C2-10; -COOR' -NR'R', halogène, OR', -COR', -CONR'R', -SR', =O, -SO3R', -SO2NR'R', -SOR', -SO2', -NO2, -CN; où R' représente indépendamment hydrogène, alkyle, alcényle ou alcynyle; n = 1, 2 ou 3; m = 1, 2, 3 ou 4. L'invention concerne également un dérivé pharmaceutiquement acceptable de ce composé, et leur utilisation dans la fabrication d'un médicament pour l'inhibition de l'action des enzymes Ca2+-ATPases. Certains composés de la formule (I) et les formulations pharmaceutiques flavone 8-lavandulyle sont nouveaux.
• 5-Alkylresorcinols from Hakea trifurcata, that cleave DNA.
  作者：William Lytollis、Ralph T. Scannell、Haoyun An、V. S. Murty、K. Sambi Reddy、John R. Barr、Sidney M. Hecht

  DOI：10.1021/ja00156a004

  日期：1995.12

  A dichloromethane extract of Hakea trifurcata that mediated relaxation of phi X174 replicative form DNA at micromolar concentrations in the presence of CU2+ was resolved into six active components by bioassay-guided fractionation. Five of the active principles were characterized structurally and shown to be 5-alkylresorcinol derivatives. These included 1,3-dihydroxy-5-tridecylbenzene (1), 1,3-dihydroxy-5-(cis-8'-pentadecenyl)benzene (2), 1,3-dihydroxy-5-[14'-(3'',5''-dihydroxyphenyl)-cis-6'-tetradecenyl]benzene (3), 1,3-dihyroxy-5-[1 4'-(3'',5''-dihydroxyphenyl)tetradecyl]benzene (4), and 1,3-dihydroxy-5-[16'-(3'',5''-dihydroxyphenyl)-cis-8'-hexadencenyl]benzene (5). The structures of these five natural principles were confirmed by total synthesis; compounds 1-5 were accessible from 3,5-dimethoxybenzaldehyde in overall yields of 59%, 27%, 15%, 16%, and 13%, respectively.
• New phenolic constituents or Grevillea robusta wood
  作者：R.S. Varma、Ms Manju、M.R. Parthasarathy

  DOI：10.1016/s0031-9422(00)97132-2

  日期：1976.1