1-(6-bromohexyloxy)-4-(methylthio)benzene | 118108-81-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-(6-bromohexyloxy)-4-(methylthio)benzene
• 英文别名: 1-[6-(4-methylthiophenoxy)hexyl]bromide；1-(6-Bromohexoxy)-4-methylsulfanylbenzene
• CAS: 118108-81-9
• 化学式: C₁₃H₁₉BrOS
• 分子量: 303.263
• InChiKey: YUUFRJASBAIEFN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  16
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  34.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(6-bromohexyloxy)-4-(methylthio)benzene 在 sodium iodide 作用下， 以 丙酮 为溶剂， 反应 6.0h， 生成 (4-((6-iodohexyl)oxy)phenyl)(methyl)sulfane
  参考文献：
  名称：

  用于合成脂肪族酯的烷基碘的铜催化烷氧基羰基化反应：氢气有所不同

  摘要：

  已开发出铜催化的未活化烷基碘的烷氧基羰基化转化。各种烷基碘可以以良好的产率转化为相应的叔丁基酯。NaO t Bu 既是亲核试剂又是碱。此外，如果添加额外的醇，也可以中等收率获得其他类型的脂肪族酯。伯醇和仲烷基醇均可成功反应。

  DOI：

  10.1021/acs.orglett.1c03071
• 作为产物：
  描述：

  6-溴正己醇 、 4-(甲硫基)苯酚 在 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 以70%的产率得到1-(6-bromohexyloxy)-4-(methylthio)benzene
  参考文献：
  名称：

  铁催化的链烯基乙酸酯的交叉偶联

  摘要：

  稳定的CO键通常在交叉偶联反应中没有反应性，而交叉偶联反应通常使用更多的亲电子卤化物或活化的酯（三氟甲磺酸酯，甲苯磺酸酯）。乙酸盐价格便宜，易于获得亲电试剂，但由于其强大的CO键和极高的参与不希望的乙酰化和去质子化的能力，因此并未用于交叉偶联中。本文报道了多种乙酸烯基酯的选择性铁催化交叉偶联，它在温和的反应条件下（0°C，2 h）与不含配体的催化剂（1-2 mol％）一起运行。

  DOI：

  10.1002/anie.201504524

文献信息

• Olefin-Assisted Iron-Catalyzed Alkylation of Aryl Chlorides
  作者：Samet Gülak、Tim N. Gieshoff、Axel Jacobi von Wangelin

  DOI：10.1002/adsc.201300095

  日期：2013.8.12

  AbstractA selective and operationally simple iron‐catalyzed cross‐coupling of aryl chlorides with alkylmagnesium halides has been developed. The reaction tolerates various functional groups and exhibits high chemoselectivity even in the presence of aryl bromides. Mechanistic studies indicate the essential role of the olefin substituent for substrate activation. Competing polymerization and reduction are effectively suppressed.magnified image
• Design, Synthesis, and Structure−Activity Relationship of Pyridyl Imidazolidinones:  A Novel Class of Potent and Selective Human Enterovirus 71 Inhibitors
  作者：Kak-Shan Shia、Wen-Tai Li、Chung-Ming Chang、Ming-Chu Hsu、Jyh-Haur Chern、Max K. Leong、Sung-Nien Tseng、Chung-Chi Lee、Yen-Chun Lee、Shu-Jen Chen、Kuan-Chang Peng、Huan-Yi Tseng、Yi-Ling Chang、Chia-Liang Tai、Shin-Ru Shih

  DOI：10.1021/jm010536a

  日期：2002.4.1

  When skeletons of Win compounds were used as templates, computer-assisted drug design led to the identification of a novel series of imidazolidinone derivatives with significant antiviral activity against enterovirus 71(EV 71), the infection of which had resulted in about 80 fatalities during the 1998 epidemic outbreak in Taiwan. In addition to inhibiting all the genotypes (A, B, and C) of EV 71 in the submicromolar to low micromolar range, compounds 1 and 8 were extensively evaluated against a variety of viruses, showing potent activity against coxsackievirus A9 (IC50 = 0.47-0.55 muM) and coxsackievirus A24 (IC50 = 0.47-0.55 muM) as well as moderate activity against enterovirus 68 (IC50 = 2.13 muM) and echovirus 9 (IC50 = 2.6 muM). Our SAR studies revealed that imidazolidinone analogues with an aryl substituent at the para position of the phenoxyl ring, such as compounds 20, 21, 27, 57, 58, and 61, in general exhibited the highest activity against EV 71. Among them, compound 20 and its corresponding hydrochloride salt 57, in terms of potency and selectivity index, appear to be the most promising candidates in this series for further development of anti-EV-71 agents. Preliminary results of the study on the mode of action by a time-course experiment suggest that test compounds 1 and 8 can effectively inhibit the virus replication at the early stages, referring to virus attachment or uncoating. This indicates that the surface protein may be the target for this type of compounds.
• US5750532A
  申请人：——

  公开号：US5750532A

  公开（公告）日：1998-05-12
• Iron-Catalyzed Cross-Coupling of Alkenyl Acetates
  作者：Dominik Gärtner、André Luiz Stein、Sabine Grupe、Johannes Arp、Axel Jacobi von Wangelin

  DOI：10.1002/anie.201504524

  日期：2015.9.1

  unreactive in cross‐coupling reactions which mostly employ more electrophilic halides or activated esters (triflates, tosylates). Acetates are cheap and easily accessible electrophiles but have not been used in cross‐couplings because the strong CO bond and high propensity to engage in unwanted acetylation and deprotonation. Reported herein is a selective iron‐catalyzed cross‐coupling of diverse alkenyl

  稳定的CO键通常在交叉偶联反应中没有反应性，而交叉偶联反应通常使用更多的亲电子卤化物或活化的酯（三氟甲磺酸酯，甲苯磺酸酯）。乙酸盐价格便宜，易于获得亲电试剂，但由于其强大的CO键和极高的参与不希望的乙酰化和去质子化的能力，因此并未用于交叉偶联中。本文报道了多种乙酸烯基酯的选择性铁催化交叉偶联，它在温和的反应条件下（0°C，2 h）与不含配体的催化剂（1-2 mol％）一起运行。
• Copper-Catalyzed Alkoxycarbonylation of Alkyl Iodides for the Synthesis of Aliphatic Esters: Hydrogen Makes the Difference
  作者：Hui-Qing Geng、Xiao-Feng Wu

  DOI：10.1021/acs.orglett.1c03071

  日期：2021.10.15

  A copper-catalyzed alkoxycarbonylation transformation of unactivated alkyl iodides has been developed. Various alkyl iodides can be converted into the corresponding tert-butyl esters in good yields. NaOtBu acts as both a nucleophile and a base. Moreover, other types of aliphatic esters can also be obtained in moderated yields if extra alcohols are added. Both primary and secondary alkyl alcohols can

  已开发出铜催化的未活化烷基碘的烷氧基羰基化转化。各种烷基碘可以以良好的产率转化为相应的叔丁基酯。NaO t Bu 既是亲核试剂又是碱。此外，如果添加额外的醇，也可以中等收率获得其他类型的脂肪族酯。伯醇和仲烷基醇均可成功反应。