2-[o-(hydroxymethyl)phenoxy]ethanol | 98954-44-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-[o-(hydroxymethyl)phenoxy]ethanol
• 英文别名: 2-(2-hydroxyethoxy)benzyl alcohol；2-(2-Hydroxy-aethoxy)-benzylalkohol；(2-Hydroxy-aethyl)-(2-hydroxymethyl-phenyl)-aether；α-Hydroxy-2-(2-hydroxy-aethoxy)-toluol；2-(2'-Hydroxyethoxy)-benzyl alcohol；2-[2-(hydroxymethyl)phenoxy]ethanol
• CAS: 98954-44-0
• 化学式: C₉H₁₂O₃
• 分子量: 168.192
• InChiKey: YHQMBXHNJDFMEY-UHFFFAOYSA-N

物化性质

• 沸点：
  325.9±22.0 °C(Predicted)
• 密度：
  1.190±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-[o-(hydroxymethyl)phenoxy]ethanol 在 manganese(IV) oxide 作用下， 以 氯仿 为溶剂， 反应 20.0h， 生成 2-(2-羟基乙氧基)苯甲醛
  参考文献：
  名称：

  Efficient Catalytic, Oxidative Lactonization for the Synthesis of Benzodioxepinones Using Thiazolium-Derived Carbene Catalysts

  摘要：

  An efficient, oxidative carbene-catalyzed lactonization reaction has been developed. Using thiazolium precatalysts, a variety of benzodioxepinone products are accessible in good to excellent yields under mild and operationally simple conditions The reaction does not require high dilution conditions and proceeds via mild and selective oxidation with azobenzene, which can easily be recovered and reused applying inexpensive FeCl3 as a formal terminal oxidant

  DOI：

  10.1021/ol101854r
• 作为产物：
  描述：

  2-(2-羟基乙氧基)苯甲醛 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 为溶剂， 生成 2-[o-(hydroxymethyl)phenoxy]ethanol
  参考文献：
  名称：

  Efficient Catalytic, Oxidative Lactonization for the Synthesis of Benzodioxepinones Using Thiazolium-Derived Carbene Catalysts

  摘要：

  An efficient, oxidative carbene-catalyzed lactonization reaction has been developed. Using thiazolium precatalysts, a variety of benzodioxepinone products are accessible in good to excellent yields under mild and operationally simple conditions The reaction does not require high dilution conditions and proceeds via mild and selective oxidation with azobenzene, which can easily be recovered and reused applying inexpensive FeCl3 as a formal terminal oxidant

  DOI：

  10.1021/ol101854r

文献信息

• A Highly Chemoselective and Rapid Chlorination of Benzyl Alcohols under Neutral Conditions
  作者：Chunbao Li、Lili Sun、Guisheng Peng、Hongmei Niu、Qiang Wang

  DOI：10.1055/s-0028-1083243

  日期：2008.12

  A rapid and highly selective chlorination method has been developedusing 2,4,6-trichloro-1,3,5-triazine (TCT) catalyzed by dimethylsulfoxide. The reactions take 10 to 40 minutes, and the yields arealmost quantitative. The neutral reaction conditions are compatiblewith substrates bearing acid-labile functional groups. Both competitiveintramolecular and intermolecular reactions for benzyl alcoholsin

  使用二甲亚砜催化的 2,4,6-三氯-1,3,5-三嗪 (TCT) 开发了一种快速、高选择性的氯化方法。反应需要 10 到 40 分钟，产率几乎是定量的。中性反应条件与带有酸不稳定官能团的底物相容。苯甲醇在脂肪醇存在下的竞争性分子内和分子间反应均表明其选择性很高。该方法已成功用于临床上使用的神经药物天麻素的选择性氯化。该程序代表了有机和药物化学中一种有用的新工具。
• Chemoselective Etherification of Benzyl Alcohols Using 2,4,6-Trichloro-1,3,5-triazine and Methanol or Ethanol Catalyzed by Dimethyl Sulfoxide
  作者：Chunbao Li、Lili Sun、Yuping Guo、Guisheng Peng

  DOI：10.1055/s-0028-1083184

  日期：——

  An efficient method for the transformation of benzyl alcohols into their methyl or ethyl ethers has been established using 2,4,6-trichloro-1,3,5-triazine (TCT) and dimethyl sulfoxide in methanol or ethanol. This procedure chemoselectively converts benzylic hydroxys into their methyl or ethyl ethers in the presence of aliphatic or phenolic hydroxys.

  一种高效的方法已利用2,4,6-三氯-1,3,5-三嗪（TCT）与二甲基亚砜在甲醇或乙醇中的反应，实现了苄醇向其甲基或乙基醚的转化。该方法能在脂肪族或酚羟基存在下，化学选择性地将苄位羟基转化为甲基或乙基醚。
• Synthesis of calix[4]crowns containing soft donor atoms and a study of their metal–cation binding properties: highly selective receptors for Cu²⁺
  作者：Muhammad Ashram

  DOI：10.1039/b205436a

  日期：——

  Two new calix[4]arenethiacrown derivatives 1 and 2 in the cone conformation were synthesized by two different pathways in good yield. Their complexation properties toward alkali, alkaline earth and transition metal cations were studied in acetonitrile at 298.15 K using a conductometric titration technique. The selectivity for Cu2+ over other cations with these novel ligands was excellent.

  合成了两种新的钙克斯[4]芳烃硫冠衍生物1和2，均为锥形构象，并且通过两种不同的方法获得了良好的产率。利用电导滴定技术，在298.15 K的乙腈中研究了它们对碱金属、碱土金属和过渡金属阳离子的络合特性。这些新型配体对Cu²⁺相对于其他阳离子的选择性表现优异。
• Sulfones as Synthetic Linchpins: Transition‐Metal‐Free sp ³ –sp ² and sp ² –sp ² Cross‐Couplings Between Geminal Bis(sulfones) and Organolithium Compounds
  作者：Barry M. Trost、Christopher A. Kalnmals

  DOI：10.1002/chem.201800118

  日期：2018.6.26

  carbon of the bis(phenylsulfonyl)methyl unit to ultimately generate trisubstituted alkenes, comprising formal sp3–sp2 and sp2–sp2 cross‐couplings between organolithium reagents and bis(sulfones). This process occurs almost instantaneously at −78 °C in the absence of any transition metals. By developing this curious transformation, it has been demonstrated that bis(phenylsulfonyl)methane is a valuable

  据报道，一种有价值的抗药性策略突出了双（苯磺酰基）甲基合成子的歧义性质，并证明了其作为合成的关键物质的效用。尽管通常将双（苯磺酰基）甲基作为sp 3碳亲核试剂引入，但事实证明，在有机锂亲核试剂存在下，它也可以作为有效的sp 2碳亲电试剂起作用。烷基锂和芳基锂与双（苯磺酰基）甲基单元的中心碳偶合，最终生成三取代的烯烃，包括形式为sp 3 –sp 2和sp 2 –sp 2的烯烃。有机锂试剂和双（砜）之间的交叉偶联。在没有任何过渡金属的情况下，该过程几乎在-78°C下瞬间发生。通过发展这种奇怪的转变，已证明双（苯磺酰基）甲烷是一种有价值的合成链节，它可以经历两个CC键形成过程，即一个sp 3-亲核体，然后进行第三次CC键形成。反应作为有效的sp 2-亲电子试剂。此发现显着增强了这个普遍存在但未充分利用的链接器组的实用性。
• Macrocyclic Ghrelin Receptor Antagonists and Inverse Agonists and Methods of Using the Same
  申请人：Hoveyda Hamid R.

  公开号：US20110105389A1

  公开（公告）日：2011-05-05

  The present invention provides novel conformationally-defined macrocyclic compounds that have been demonstrated to be selective modulators of the ghrelin receptor (GRLN, growth hormone secretagogue receptor, GHS-R1a and subtypes, isoforms and/or variants thereof). Methods of synthesizing the novel compounds are also described herein. These compounds are useful as antagonists or inverse agonists of the ghrelin receptor and as medicaments for treatment and prevention of a range of medical conditions including, but not limited to, metabolic and/or endocrine disorders, obesity and obesity-associated disorders, appetite or eating disorders, addictive disorders, cardiovascular disorders, gastrointestinal disorders, genetic disorders, hyperproliferative disorders, central nervous system disorders and inflammatory disorders.

  本发明提供了新型构象定义的大环化合物，已被证明是生长激素分泌素受体（GRLN，生长激素分泌素受体，GHS-R1a及其亚型、异构体和/或变种）的选择性调节剂。本文还描述了合成这些新型化合物的方法。这些化合物可用作生长激素分泌素受体的拮抗剂或逆向激动剂，以及用于治疗和预防一系列医学疾病，包括但不限于代谢和/或内分泌紊乱、肥胖和与肥胖相关的疾病、食欲或进食紊乱、成瘾紊乱、心血管疾病、胃肠道疾病、遗传疾病、过度增殖性疾病、中枢神经系统疾病和炎症性疾病。