(+/-)-1-bromo-3-(4-methoxyphenyloxy)-2-propanol | 95302-25-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (+/-)-1-bromo-3-(4-methoxyphenyloxy)-2-propanol
• 英文别名: 1-bromo-3-(4-methoxy-phenoxy)-propan-2-ol；1-bromo-3-(4-methoxyphenoxy)-2-propanol；1-bromo-3-(4-methoxyphenoxy)propan-2-ol；1-(p-tolyloxy)-3-bromo-2-propanol
• CAS: 95302-25-3；140696-02-2；140647-14-9
• 化学式: C₁₀H₁₃BrO₃
• 分子量: 261.115
• InChiKey: QEZDOAQPFHNGDZ-UHFFFAOYSA-N

物化性质

• 沸点：
  375.6±32.0 °C(Predicted)
• 密度：
  1.438±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 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-bromo-3-(4-methoxyphenyloxy)-2-propanol 生成 2-Propanol, 1-bromo-3-(4-methoxyphenoxy)-
  参考文献：
  名称：

  Resolution of Racemic O-(4-Methoxyphenyl)glycidol

  摘要：

  Racemic O-(4-methoxyphenyl)glycidol has been resolved in three steps by employing lipase mediated kinetic acylation of the halohydrin intermediates.

  DOI：

  10.3987/com-91-5934
• 作为产物：
  描述：

  4-甲氧基苯酚 在 sodium hydroxide 、 四甲基氯化铵 、 溶剂黄146 、 lithium bromide 作用下， 以 四氢呋喃 为溶剂， 反应 43.0h， 生成 (+/-)-1-bromo-3-(4-methoxyphenyloxy)-2-propanol
  参考文献：
  名称：

  Resolution of Racemic O-(4-Methoxyphenyl)glycidol

  摘要：

  Racemic O-(4-methoxyphenyl)glycidol has been resolved in three steps by employing lipase mediated kinetic acylation of the halohydrin intermediates.

  DOI：

  10.3987/com-91-5934

文献信息

• The halogen-mediated opening of epoxides in the presence of pyridine-containing macrocycles
  作者：Hashem Sharghi、Khodabakhsh Niknam、Maryam Pooyan

  DOI：10.1016/s0040-4020(01)00443-4

  日期：2001.7

  The ring opening of epoxides with elemental iodine and bromine in the presence of three pyridine-containing macrocyclic diamides as new catalysts affords vicinal iodo alcohols and bromo alcohols in high yields. This new procedure occurs regioselectively under mild conditions in various aprotic solvents. The catalysts are easily recovered and can be reused several times.

  在作为新催化剂的三种含吡啶大环二酰胺的存在下，环氧化物与元素碘和溴的开环提供了高产率的邻位碘代醇和溴代醇。这种新方法在温和条件下在各种非质子传递溶剂中区域选择性地发生。催化剂易于回收，可以重复使用多次。
• Allyltin tribromide: A versatile reagent involved in the ring-opening of epoxides
  作者：GuoHong Chen、Xin Wang、XiaoQian Jin、LingYan Liu、WeiXing Chang、Jing Li

  DOI：10.1007/s11426-010-3200-3

  日期：2010.6

  This paper presents a versatile reagent for epoxide cleavage. The allyltin tribromide could act as a novel and easily prepared allylation reagent and halide atom donor to convert epoxides to the corresponding homoallyl alcohols and halohydrins in high yields with excellent regioselectivities under mild reaction conditions, respectively. It could also act as a Lewis acid to catalyze the ring opening

  本文提出了一种用于环氧化物裂解的通用试剂。三溴化烯丙基锡可以作为一种新颖且易于制备的烯丙基化试剂和卤化物原子供体，分别在温和的反应条件下以高收率将环氧化物高产率地转化为相应的烯丙基醇和卤代醇。它也可以作为路易斯酸来催化环氧化物与醇的开环反应。
• Monobromoborane - Dimethyl Sulfide—a Highly Promising Reagent for the Regio- and Chemoselective Brominative Cleavage of Terminal Epoxides into Vicinal Bromohydrins
  作者：Chandra D. Roy、Herbert C. Brown

  DOI：10.1071/ch06408

  日期：——

  Monobromoborane–dimethyl sulfide (BH2Br–SMe2) is a highly regio- and chemoselective reagent useful for the brominative cleavage of the epoxy moiety into bromohydrins in the presence of alkenes, alkynes, ethers, acetals, ketals, and acetonides at 0°C, besides being an excellent hydroborating reagent. Several reactive functional groups, such as chloride, ketones, esters, nitriles, nitros, and thioethers, have been accommodated during such transformations. Although the reduction of acetophenone was completely suppressed at –25°C, 4-chlorobenzaldehyde still underwent 12–13% reduction of an aldehydic group.

  单溴硼烷二甲基硫醚（BH2Br-SMe2）是一种具有高度区域性和化学选择性的试剂，除了是一种出色的氢硼酸化试剂外，还可在 0°C 温度下，在烯、炔、醚、乙缩醛、酮和丙酮的存在下，将环氧分子溴化裂解成溴水酐。在这种转化过程中，可以容纳多种活性官能团，如氯化物、酮、酯、腈、亚硝基和硫醚。虽然苯乙酮的还原反应在零下 25 摄氏度时被完全抑制，但 4-氯苯甲醛仍能还原 12-13% 的醛基。
• Design, synthesis and biological evaluation of novel 1,2,3-triazolyl $$\upbeta $$ β -hydroxy alkyl/carbazole hybrid molecules
  作者：Mohammad Navid Soltani Rad、Somayeh Behrouz、Marzieh Behrouz、Akram Sami、Mehdi Mardkhoshnood、Ali Zarenezhad、Elham Zarenezhad

  DOI：10.1007/s11030-016-9678-7

  日期：2016.8

  The design, synthesis and biological study of several novel 1,2,3-triazolyl \(\upbeta \)-hydroxy alkyl/carbazole hybrid molecules as a new type of antifungal agent has been described. In this synthesis, the N-alkylation reaction of carbazol-9-ide potassium salt with 3-bromoprop-1-yne afforded 9-(prop-2-ynyl)-9H-carbazole. The ‘Click’ Huisgen cycloaddition reaction of 9-(prop-2-ynyl)-9H-carbazole with

  已经描述了几种新型的1,2,3-三唑基（upbeta） -羟基烷基/咔唑杂化分子作为新型抗真菌剂的设计，合成和生物学研究。在该合成中，Ñ与3-溴丙-1-炔，得到9-（丙-2-炔基）-9咔唑-9- IDE钾盐烷基化反应ħ -咔唑。具有不同\（\ upbeta \）的9-（prop-2- ynyl）-9 H-咔唑的'Click'Huisgen环加成反应掺杂铜的二氧化硅硫酸亚铜的存在下，叠氮基叠氮化物醇可以极高的收率产生目标分子。针对各种病原性真菌菌株，革兰氏阳性和/或革兰氏阴性细菌筛选了标题化合物的体外抗真菌和抗菌活性。特别地，证明了1-（4-（（9 H-咔唑-9-甲基）甲基）-1 H -1,2,3-三唑-1-基）-3-丁氧基丙烷-2-醇（10e）与氟康唑和克霉唑相比，作为已研究的参考药物，它对所有真菌测试均具有有效的抗真菌活性。我们的分子对接分析揭示了化合物10e与分枝杆菌P450DM酶活性
• ‘Click Synthesis’ of Some Novel O-Substituted Oximes Containing 1,2,3-Triazole-1,4-diyl Residues as New Analogs of β-Adrenoceptor Antagonists
  作者：Mohammad Navid Soltani Rad、Somayeh Behrouz、Fatemeh Karimitabar、Ali Khalafi-Nezhad

  DOI：10.1002/hlca.201100324

  日期：2012.3

  The ‘click synthesis’ of some novel O‐substituted oximes, 7a–7t, which contain 1,2,3‐triazolediyl residues, as new analogs of β‐adrenoceptor antagonists is described (Schemes 1–4). The synthesis of these compounds was achieved in four to five steps. The formation of oximes of 9H‐fluoren‐9‐one and benzophenone, i.e., 9a and 9b, respectively, followed by their reaction with propargyl bromide, afforded

  一些新颖的“点击合成” ø取代的肟，7A - 7吨，其含有1,2,3-三唑二基，作为新的类似物β -肾上腺素能受体拮抗剂被描述（方案1 - 4）。这些化合物的合成需要四到五个步骤。9本肟的形成ħ芴-9-酮和二苯甲酮，即，图9a和图9b分别，得到随后通过它们与炔丙基溴反应ö -propargyl肟10A和10B，分别，其通过随后的CuI催化惠斯根用制备的β-叠氮基醇11a – 11j进行环加成反应（方案2和3），得到的目标化合物7a – 7t的收率很高。