1,3-二甲氧基-5-(5-羟基戊基)苯 | 836-27-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1,3-二甲氧基-5-(5-羟基戊基)苯
• 英文名称: 5-(3,5-dimethoxyphenyl)pentan-1-ol
• 英文别名: 1,3-dimethoxy-5-(5-hydroxypentyl)benzene；5-(3,5-dimethoxyphenyl)-1-pentanol；4-(3',5'-Dimethoxyphenyl)-pentan-1-ol；5-(3,5-Dimethoxy-phenyl)-pentanol-(1)；5-(3,5-Dimethoxyphenyl)pentan-1-ol
• CAS: 836-27-1
• 化学式: C₁₃H₂₀O₃
• 分子量: 224.3
• InChiKey: IJTAGKZHQOCIIZ-UHFFFAOYSA-N

物化性质

• 沸点：
  145-155 °C(Press: 0.01 Torr)
• 密度：
  1.032±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,3-二甲氧基-5-(5-羟基戊基)苯 在 lithium aluminium tetrahydride 、 四溴化碳 、 三氟化硼乙醚 、 三溴化硼 、 magnesium sulfate 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 24.25h， 生成 四氢大麻酚
  参考文献：
  名称：

  Δ⁹-Tetrahydrocannabinol Immunochemical Studies:  Haptens, Monoclonal Antibodies, and a Convenient Synthesis of Radiolabeled Δ⁹-Tetrahydrocannabinol

  摘要：

  Immunopharmacotherapy as an approach to combat drugs of abuse has become an active area of investigation. Marijuana is the most commonly used illicit drug in the U.S. The main active chemical in marijuana is Delta(9)-tetrahydrocannabinol (Delta(9)-THC); hence, monoclonal antibodies with high affinity and specificity for Delta(9)-tetrahydrocannabinol could be valuable immunopharmacotherapeutic intervention and diagnostic tools. We have synthesized immunoconjugates that induce an effective immune response to Delta(9)-THC and describe a convenient synthesis of radiolabeled Delta(9)-THC. We demonstrate the value and use of this probe to select anti-Delta(9)-THC antibodies that bind Delta(9)-THC with good affinity. The synthetic route to radiolabeled Delta(9)-THC has enabled the correct assessment of the affinity of these antibodies to their ligand and may facilitate future binding studies between Delta(9)-THC and its analogues and the cannabinoid receptors.

  DOI：

  10.1021/jm050442r
• 作为产物：
  描述：

  (E)-1,3-dimethoxy-5-(pent-1-en-1-yl)benzene 在 sodium hydroxide 、 sodium tetrahydroborate 、 三氟化硼乙醚 、 双氧水 作用下， 生成 1,3-二甲氧基-5-(5-羟基戊基)苯
  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

• 5-Alkylresorcinol Derivatives from the Bryozoan Schizomavella mamillata: Isolation, Synthesis, and Antioxidant Activity
  作者：María Ortega、Juan Pantoja、Carolina de los Reyes、Eva Zubía

  DOI：10.3390/md15110344

  日期：——

  corresponding 1,3-disulfates. Schizol A (1) has been synthetized from 3,5-dimethoxybenzaldehyde through a sequence involving a Wittig reaction for the construction of the C-1',C-2' bond and a Julia-Kocienski olefination for the synthesis of the C-5',C-6' double bond. In the ABTS (2,2'-azinobis(3-ethylbenzothiazoline-6-sulphonic acid)) antioxidant assay, the natural compounds schizol A (1) and schizol B (2)

  对苔藓菌Schizomavella mamillata的化学研究导致分离出六种新的5-烷基间苯二酚衍生物，schizols AF（1-6），其结构是通过分光光度法确定的。schizol A（1）表现出与间苯二酚环的C-5连接的（E）-6-苯基非-5-烯基部分，而在schizol B（2）中，C-5的取代基包含一个不寻常的1,2-二氢环丁苯部分。schizols C（3）和D（4）分别被表征为1和2的1-硫酸盐衍生物，schizols E（5）和F（6）是相应的1,3-二硫酸盐。Schizol A（1）已通过3,5-二甲氧基苯甲醛通过涉及Wittig反应的C-1'，C-2'键的构建和Julia-Kocienski烯烃合成C-5的序列合成'，C-6'双键。在ABTS（2,2'
• ANGIOGENIC RESORCINOL DERIVATIVES
  申请人：Makriyannis Alexandros

  公开号：US20120172339A1

  公开（公告）日：2012-07-05

  Novel resorcinol derivatives and methods of preparation and use are presented. These compounds can stimulate angiogenesis as a biological function triggered by the activation of one cannabinoid receptor distinct from CB1 and CB2. Thus, these compounds are specific ligands for one cannabinoid receptor distinct from CB1 and CB2. The invented compounds, when administered in a therapeutically effective amount to an individual or animal, results in a sufficiently high level of that compound in the individual or animal to cause a physiological response. The physiological response may be useful to treat a number of physiological conditions.

  本发明提供了新型间苯二酚衍生物的制备方法和用途。这些化合物可以刺激血管生成，作为一种由激活与CB1和CB2不同的一种大麻素受体而触发的生物学功能。因此，这些化合物是与CB1和CB2不同的一种大麻素受体的特异性配体。当以治疗有效量的方式向个体或动物施用这些发明化合物时，会在个体或动物中产生足够高的该化合物水平，从而引起生理反应。这种生理反应可能有助于治疗许多生理状况。
• Huisgen,R. et al., Justus Liebigs Annalen der Chemie, 1964, vol. 677, p. 21 - 33
  作者：Huisgen,R. et al.

  DOI：——

  日期：——
• Synthesis of 5′,11-dihydroxy-Δ8-tetrahydrocannabinol
  作者：John W. Huffman、Ming-Jung Wu、W.Kenneth Banner、Dong Dai

  DOI：10.1016/s0040-4020(97)00868-5

  日期：1997.9

  The synthesis of a polar cannabinoid, 5',11-dihydroxy-Delta(8)-tetrahydrocannabinol (2), has been carried out. A key step in the synthesis is the reaction of an aryllithium derived from 1-(tert-butyldimethylsilyloxy)-5-(3, 5-dimethoxyphenyl)pentane with apoverbenone. Subsequent conversions provided diol 2, which has significantly less affinity for the cannabinoid receptor than Delta(8)-THC. (C) 1997 Elsevier Science Ltd.
• Identification of Novel ROS Inducers: Quinone Derivatives Tethered to Long Hydrocarbon Chains
  作者：Yeonsun Hong、Sandip Sengupta、Wooyoung Hur、Taebo Sim

  DOI：10.1021/jm501846y

  日期：2015.5.14

  We performed the first synthesis of the 17-carbon chain-tethered quinone moiety 22 (SAN5201) of irisferin A, a natural product exhibiting anticancer activity, and its derivatives. We found that 22 is a potent ROS inducer and cytotoxic agent. Compound 25 (SAN7401), the hydroquinone form of 22, induced a significant release of intracellular ROS and apoptosis (EC50 = 1.3-2.6 mu M) in cancer cell lines, including A549 and HCT-116. Compared with the activity of a well-known ROS inducer, piperlongumine, 22 and 25 showed stronger cytotoxicity and higher selectivity over noncancerous cells. Another hydroquinone tethering 12-carbon chain, 26 (SAN4601), generated reduced levels of ROS but showed more potent cytotoxicity (EC50 = 0.8-1.6 mu M) in cancer cells, although it lacked selectivity over noncancerous cells, implying that the naturally occurring 17-carbon chain is also crucial for ROS production and a selective anticancer effect. Both 25 and 26 displayed strong, equipotent activities against vemurafenib-resistant SK-Mel2 melanoma cells and p53-deficient H1299 lung cancer cells as well, demonstrating their broad therapeutic potential as anticancer agents.