5-(5'-bromopentyl)-1,3-dimethoxybenzene | 886-52-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-(5'-bromopentyl)-1,3-dimethoxybenzene
• 英文别名: 1-(5-bromopentyl)-3,5-dimethoxybenzene；5-<3,5-Dimethoxy-phenyl>-pentylbromid-(1)；4-(3',5'-Dimethoxyphenyl)-1-brompentan
• CAS: 886-52-2
• 化学式: C₁₃H₁₉BrO₂
• 分子量: 287.197
• InChiKey: MBQICLDDHZFUAW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 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：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-(5'-bromopentyl)-1,3-dimethoxybenzene 在 lithium aluminium tetrahydride 、 三氟化硼乙醚 、 三溴化硼 、 magnesium sulfate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 10.25h， 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：

  在 四溴化碳 、 palladium on activated charcoal 、 氢气 、 三苯基膦 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 17.0h， 生成 5-(5'-bromopentyl)-1,3-dimethoxybenzene
  参考文献：
  名称：

  粟酒裂殖酵母的5-烷基间苯二酚衍生物：分离，合成和抗氧化活性。

  摘要：

  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'

  DOI：

  10.3390/md15110344

文献信息

• Huisgen,R. et al., Justus Liebigs Annalen der Chemie, 1964, vol. 677, p. 21 - 33
  作者：Huisgen,R. et al.

  DOI：——

  日期：——
• 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.
• Cannon,J.R.; Metcalf,B.W., Australian Journal of Chemistry, 1973, vol. 26, p. 2277 - 2290
  作者：Cannon,J.R.、Metcalf,B.W.

  DOI：——

  日期：——
• Δ⁹-Tetrahydrocannabinol Immunochemical Studies:  Haptens, Monoclonal Antibodies, and a Convenient Synthesis of Radiolabeled Δ⁹-Tetrahydrocannabinol
  作者：Longwu Qi、Noboru Yamamoto、Michael M. Meijler、Laurence J. Altobell、George F. Koob、Peter Wirsching、Kim D. Janda

  DOI：10.1021/jm050442r

  日期：2005.11.1

  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.
• 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'