(1R,5S)-2-(4-Bromo-butyl)-6,6-dimethyl-bicyclo[3.1.1]hept-2-ene | 461417-86-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1R,5S)-2-(4-Bromo-butyl)-6,6-dimethyl-bicyclo[3.1.1]hept-2-ene
• 英文别名: (1R,5S)-2-(4-bromobutyl)-6,6-dimethylbicyclo[3.1.1]hept-2-ene
• CAS: 461417-86-7
• 化学式: C₁₃H₂₁Br
• 分子量: 257.214
• InChiKey: NFJJEEJUWSNSBJ-RYUDHWBXSA-N

物化性质

• 沸点：
  286.1±19.0 °C(Predicted)
• 密度：
  1.176±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  (1R,5S)-2-(4-Bromo-butyl)-6,6-dimethyl-bicyclo[3.1.1]hept-2-ene 在 cesium hydroxide 、 2,6-二叔丁基-4-甲基苯酚 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 168.0h， 生成 (1R,5S)-2-(4-hydroperoxybutyl)-6,6-dimethylbicyclo[3.1.1]hept-2-ene
  参考文献：
  名称：

  Synthesis of cardamom peroxide analogues by radical cyclization of hydroperoxyalkenes

  摘要：

  Three pinenic hydroperoxides were synthesized according to the Dussault method. Two of them could cyclize under radical conditions to give the exo-trig isomer as a single regioisomer. Only five- and six-member ring peroxides were obtained, whereas none of the possible seven-member ones was observed. This strategy could be employed in the total synthesis of cardamom peroxide. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)01122-x
• 作为产物：
  描述：

  beta-pinene 在 吡啶 、 sodium tetrahydroborate 、 N-溴代丁二酰亚胺(NBS) 、 三苯基膦 、 zinc dibromide 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 生成 (1R,5S)-2-(4-Bromo-butyl)-6,6-dimethyl-bicyclo[3.1.1]hept-2-ene
  参考文献：
  名称：

  Monoterpene-Containing Substituted Coumarins as Inhibitors of Respiratory Syncytial Virus (RSV) Replication

  摘要：

  呼吸道合胞病毒（RSV）是婴儿死亡的一个重要原因。然而，目前尚无疫苗和足够的药物用于治疗。我们首次展示，O-连接的香豆素-单萜共轭物是有效的RSV抑制剂。最有效的化合物对RSV的A型和B型两种血清型都具有活性。根据添加时间实验的结果，这些共轭物在病毒周期的早期阶段起作用。根据分子模拟数据，RSV F蛋白可能被视为一个可能的靶点。

  DOI：

  10.3390/molecules26247493

文献信息

• New Inhibitors of Respiratory Syncytial Virus (RSV) Replication Based on Monoterpene-Substituted Arylcoumarins
  作者：Tatyana M. Khomenko、Anna A. Shtro、Anastasia V. Galochkina、Yulia V. Nikolaeva、Anzhelika V. Garshinina、Sophia S. Borisevich、Dina V. Korchagina、Konstantin P. Volcho、Nariman F. Salakhutdinov

  DOI：10.3390/molecules28062673

  日期：——

  Respiratory syncytial virus (RSV) causes annual epidemics of respiratory infection. Usually harmless to adults, the RSV infection can be dangerous to children under 3 years of age and elderly people over 65 years of age, often causing serious problems, even death. At present, there are no vaccines and specific chemotherapeutic agents for the treatment of this disease, so the search for low-molecular weight compounds to combat RSV is a challenge. In this work, we have shown, for the first time, that monoterpene-substituted arylcoumarins are efficient RSV replication inhibitors at low micromolar concentrations. The most active compound has a selectivity index of about 200 and acts most effectively at the early stages of infection. The F protein of RSV is a potential target for these compounds, which is also confirmed by molecular docking and molecular dynamics simulation data.

  呼吸道合胞病毒（RSV）每年都会引起呼吸道感染流行。通常情况下，RSV 对成人无害，但对 3 岁以下儿童和 65 岁以上老人来说，RSV 感染可能很危险，往往会造成严重问题，甚至死亡。目前，还没有治疗这种疾病的疫苗和特异性化疗药物，因此寻找抗 RSV 的低分子量化合物是一项挑战。在这项研究中，我们首次发现单萜取代的芳基香豆素类化合物在低微摩尔浓度下是高效的 RSV 复制抑制剂。活性最高的化合物的选择性指数约为 200，在感染的早期阶段发挥最有效的作用。RSV 的 F 蛋白是这些化合物的潜在靶标，分子对接和分子动力学模拟数据也证实了这一点。
• Synthesis and antimalarial activity of 2-methoxyprop-2-yl peroxides derivatives
  作者：Laure Cointeaux、Jean-François Berrien、Viviane Peyrou、Olivier Provot、Liliane Ciceron、Martin Danis、Anne Robert、Bernard Meunier、Joëlle Mayrargue

  DOI：10.1016/s0960-894x(02)00837-5

  日期：2003.1

  2-Methoxyprop-2-yl peroxides were synthesized and evaluated in vitro against Plasmodium falciparum. These acyclic artemisinin-related peroxides revealed moderate to good activity but were devoid of alkylating property towards the synthetic model of heme Mn-II-TPP. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Monoterpene-Containing Substituted Coumarins as Inhibitors of Respiratory Syncytial Virus (RSV) Replication
  作者：Tatyana M. Khomenko、Anna A. Shtro、Anastasia V. Galochkina、Yulia V. Nikolaeva、Galina D. Petukhova、Sophia S. Borisevich、Dina V. Korchagina、Konstantin P. Volcho、Nariman F. Salakhutdinov

  DOI：10.3390/molecules26247493

  日期：——

  Respiratory syncytial virus (RSV) is a critical cause of infant mortality. However, there are no vaccines and adequate drugs for its treatment. We showed, for the first time, that O-linked coumarin–monoterpene conjugates are effective RSV inhibitors. The most potent compounds are active against both RSV serotypes, A and B. According to the results of the time-of-addition experiment, the conjugates act at the early stages of virus cycle. Based on molecular modelling data, RSV F protein may be considered as a possible target.

  呼吸道合胞病毒（RSV）是婴儿死亡的一个重要原因。然而，目前尚无疫苗和足够的药物用于治疗。我们首次展示，O-连接的香豆素-单萜共轭物是有效的RSV抑制剂。最有效的化合物对RSV的A型和B型两种血清型都具有活性。根据添加时间实验的结果，这些共轭物在病毒周期的早期阶段起作用。根据分子模拟数据，RSV F蛋白可能被视为一个可能的靶点。
• Synthesis of cardamom peroxide analogues by radical cyclization of hydroperoxyalkenes
  作者：Laure Cointeaux、Jean-François Berrien、Joëlle Mayrargue

  DOI：10.1016/s0040-4039(02)01122-x

  日期：2002.8

  Three pinenic hydroperoxides were synthesized according to the Dussault method. Two of them could cyclize under radical conditions to give the exo-trig isomer as a single regioisomer. Only five- and six-member ring peroxides were obtained, whereas none of the possible seven-member ones was observed. This strategy could be employed in the total synthesis of cardamom peroxide. (C) 2002 Elsevier Science Ltd. All rights reserved.