5-(5-溴戊基)苯-1,3-二醇 | 58545-34-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: 5-(5-溴戊基)苯-1,3-二醇
• 英文名称: 1-(5-bromopentyl)benzene-1,3-diol
• 英文别名: 5'-bromo olivetol；5-(5'-bromopentyl)resorcinol；1-(3',5'-Dihydroxyphenyl)-5-brompentan；1-bromo-5-(3,5-dihydroxy-phenyl)-pentane；1,3-Benzenediol, 5-(5-bromopentyl)-；5-(5-bromopentyl)benzene-1,3-diol
• CAS: 58545-34-9
• 化学式: C₁₁H₁₅BrO₂
• 分子量: 259.143
• InChiKey: GMTNLSIDZHTTPR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-(5-溴戊基)苯-1,3-二醇 在 lithium aluminium tetrahydride 、 三氟化硼乙醚 、 magnesium sulfate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.5h， 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：

  5-(5'-bromopentyl)-1,3-dimethoxybenzene 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 6.75h， 以98%的产率得到5-(5-溴戊基)苯-1,3-二醇
  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

文献信息

• Synthesis of Cannabinoid Model Compounds. Part 3. (6aR, 10aR)-N-ethyl-?8-tetrahydrocannabinol-18-amide, (6aR, 10aR, 17RS)-N-ethyl-17-methyl-?8- tetrahydrocannabinol-18-amide and (6aR, 10aR)-17,18-didehydro-?8-tetrahydrocannabinol
  作者：Burkhard Schmidt、Ingo Franke、Franz-Josef Witteler、Michael Binder

  DOI：10.1002/hlca.19830660822

  日期：1983.12.14

  The novel cannabinoids (6aR, 10aR)-N-ethyl-Δ8-tetrahydrocannabinol-18-amide (15) and (6aR, 10aR, 17 RS)-N-ethyl-17-methyl-Δ8- tetrahydrocannabinol-18-amide (16), designed as cannabinoid affinity ligands, were synthesized from the corresponding acids 11 and 12via the N-hydroxysuccinimide esters. Amide 16 was tested in the rat and was generalized to Δ9-tetrahydrocannabinol, being 5 times less potent

  新颖的大麻素（6A - [R，10A - [R ）- ñ -乙基- Δ 8四氢大麻酚-18-酰胺（15）和（6A - [R，10A - [R，17个RS） - ñ -乙基-17-甲基Δ 8 -四氢-18 -酰胺（16） ，设计为大麻素亲和配体，从该相应的酸合成11和12经由所述ñ羟基琥珀酰亚胺酯。酰胺16在大鼠中测试和推广到Δ 9-四氢大麻酚，效力比训练药低5倍。（6a的改进的合成- [R，10A - [R）-17,18二脱氢Δ 8四氢大麻酚（23）进行报告。至于制备模型反应氚代Δ 8四氢大麻酚，化合物23被选择性地在C（17）和在苯C（18）/ ET氘化3 N使用[（C 6 H ^ 5）3 P] 3的RuCl 2作为催化剂。
• The synthesis of deuterium, carbon-14, and carrier-free tritium labeled cannabinoids
  作者：C. G. Pitt、D. T. Hobbs、H. Schran、C. E. Twine、D. L. Williams

  DOI：10.1002/jlcr.2590110412

  日期：——

  1′,2′-Dehydroolivetol and its monomethyl ether, 5′-bromoolivetol, and olivetol-5,-2H3, have been synthesized. Acid catalyzed condensation of the latter three compounds with p-mentha-2,8-dien-1-ol gave 1′,2′-dehydro-Δ8-THC methyl ether, 5′-bromo-Δ8-THC, and Δ9-THC-5′-2H3, respectively. 5′-Bromo-Δ8-THC served as a precursor of 4′,5′-dehydro-Δ8- and Δ8-THC, 4′- and 5′-hydroxy-Δ8-THC, 5′-dimethylamino-Δ8-THC and 5′-carboxy-Δ8-THC. Reduction of 4′,5′-dehydro-Δ8- and Δ9-THC in the presence of homogeneous catalysts afforded tritium labeled Δ8-THC (50 Ci/mmole) and Δ9-THC (58 Ci/mmole), respectively. Syntheses of Δ9-THC-11-2H3, Δ9-THC-11-14C cannabinol-5,-2H3′ and other labeled cannabinoids are described.

  1′,2′-Dehydroolivetol 及其单甲醚、5′-bromoolivetol 和 olivetol-5,-2H3已被合成。在酸催化下，后三种化合物与对薄荷-2,8-二烯-1-醇缩合，分别得到 1′,2′-脱氢-Δ8-THC 甲醚、5′-溴-Δ8-THC 和 Δ9-THC-5′-2H3。5′-Bromo-Δ8-THC 是 4′、5′-脱氢-Δ8-和Δ8-THC、4′-和 5′-羟基-Δ8-THC、5′-二甲氨基-Δ8-THC 和 5′-羧基-Δ8-THC 的前体。在均相催化剂存在下还原 4′,5′-脱氢-Δ8-和 Δ9-THC，分别得到氚标记的 Δ8-THC（50 Ci/mmole）和 Δ9-THC（58 Ci/mmole）。介绍了Δ9-THC-11-2H3、Δ9-THC-11-14C 大麻酚-5,-2H3′ 和其他标记大麻素的合成。
• ONE-STEP FLOW-MEDIATED SYNTHESIS OF CANNABIDIOL (CBD) AND DERIVATIVES
  申请人：TRUSTEES OF BOSTON UNIVERSITY

  公开号：US20200325091A1

  公开（公告）日：2020-10-15

  Herein are described apparatus and processes for the preparation of cannabinoids, such as cannabidiol (CBD) and derivatives thereof. The apparatus and processes described can be used for the one-step, flow-mediated synthesis of cannabidiol and derivatives with improved overall yield, material throughput, and product purity relative to batch processes.

  本文描述了用于制备大麻素（如大麻二酚CBD）及其衍生物的装置和工艺。所描述的装置和工艺可用于一步法、流程介导的合成大麻二酚及其衍生物，相对于批处理过程，具有更高的总产量、材料通过量和产品纯度。
• One-step flow-mediated synthesis of cannabidiol (CBD) and derivatives
  申请人：TRUSTEES OF BOSTON UNIVERSITY

  公开号：US10981850B2

  公开（公告）日：2021-04-20

  Herein are described apparatus and processes for the preparation of cannabinoids, such as cannabidiol (CBD) and derivatives thereof. The apparatus and processes described can be used for the one-step, flow-mediated synthesis of cannabidiol and derivatives with improved overall yield, material throughput, and product purity relative to batch processes.

  本文描述了制备大麻素（如大麻二酚（CBD）及其衍生物）的设备和工艺。所述设备和工艺可用于一步法、流动介导合成大麻二酚及其衍生物，与批量工艺相比，总体产量、材料吞吐量和产品纯度均有所提高。
• 5'-Azido-.DELTA.8-THC: a novel photoaffinity label for the cannabinoid receptor
  作者：Avgui Charalambous、Guo Yan、Devin B. Houston、Allyn C. Howlett、David R. Compton、Billy R. Martin、Alexandros Makriyannis

  DOI：10.1021/jm00094a023

  日期：1992.8