2-(hydroxymethyl)phenyl 4-methyl-1-benzenesulfonate | 210688-98-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(hydroxymethyl)phenyl 4-methyl-1-benzenesulfonate
• 英文别名: 4-tosyloxybenzyl alcohol；2-HOCH2C6H4OTs；C6H4(p-OTs)CH2OH；2-(4-OTs)C6H4CH2OH；[2-(Hydroxymethyl)phenyl] 4-methylbenzenesulfonate
• CAS: 210688-98-5
• 化学式: C₁₄H₁₄O₄S
• 分子量: 278.329
• InChiKey: HDMYFJVMFCBACK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  72
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(hydroxymethyl)phenyl 4-methyl-1-benzenesulfonate 在 氯化亚砜 、 苄基三乙基氯化铵 作用下， 以 sodium hydroxide 、 苯 为溶剂， 反应 31.5h， 生成 1-(2'-hydroxyfenilmethyl)isoquinoline
  参考文献：
  名称：

  Collado, Daniel; Perez-Inestrosa, Ezequiel; Suau, Rafael, Organic letters, 2002, vol. 4, # 5, p. 855 - 858

  摘要：

  DOI：
• 作为产物：
  描述：

  2-formylphenyl tosylate 在 甲醇 、 sodium tetrahydroborate 作用下， 反应 4.0h， 以87%的产率得到2-(hydroxymethyl)phenyl 4-methyl-1-benzenesulfonate
  参考文献：
  名称：

  Synthesis, characterization and structures of 2-(3,5-dimethylpyrazol-1-yl)ethylseleno derivatives and their probable glutathione peroxidase (GPx) like activity

  摘要：

  合成了一系列2-(3,5-二甲基吡唑-1-基)乙基硒衍生物。研究了这些化合物在模型系统中的谷胱甘肽过氧化物酶样催化活性，其中利用有机硒化合物存在下，用二硫苏糖醇（DTTred）还原过氧化氢，通过1H NMR光谱进行研究。所有这些化合物均表现出GPx样催化活性，催化反应通过一种硒氧化物中间体进行，该中间体由77Se{1H} NMR光谱鉴定。

  DOI：

  10.1039/c0ob00807a

文献信息

• Chemoselective Carbonyl Reduction of Functionalised Aldehydes and Ketones to Alcohols with Sodium Dithionite
  作者：Jasvinder Singh、Goverdhan L. Kad、Munisha Sharma、R. S. Dhillon

  DOI：10.1080/00397919808007041

  日期：1998.6

  Abstract Sodium dithionite efficiently reduces carbonyl functionalities of functionalised aldehydes and ketones to corresponding alcohols in good yields without effecting the other functional groups in water/dioxane system at 85°C.

  摘要 连二亚硫酸钠有效地将官能化醛和酮的羰基官能团以良好的收率还原为相应的醇，而不会影响 85°C 水/二恶烷体系中的其他官能团。
• An Efficient Organocatalyzed Interconversion of Silyl Ethers to Tosylates Using DBU and <i>p</i>-Toluenesulfonyl Fluoride
  作者：Vincent Gembus、Francis Marsais、Vincent Levacher

  DOI：10.1055/s-2008-1078407

  日期：2008.6

  A mild and efficient interconversion from silyl ethers to sulfonates esters is reported with good yields. This silyl-sulfonyl exchange proceeds readily in acetonitrile at room temperature in the presence of p-toluenesulfonyl fluoride and a catalytic amount of 1,8-diazabicyclo[5.4.0]undec-7ene (DBU). This method can be used with trimethysilyl (TMS), triethylsilyl (TES) and tert-butyldimethylsilyl (TBDMS) ethers.

  报道了一种温和且高效的硅醚转化为磺酸酯的方法，获得了良好的产率。这种硅-磺酰交换在室温下的乙腈中，在对甲苯磺酰氟和催化量的1,8-二氮杂双环[5.4.0]十一烯（DBU）存在下容易进行。该方法可以用于三甲基硅基（TMS）、三乙基硅基（TES）和叔丁基二甲基硅基（TBDMS）醚。
• Synthesis, characterization and structures of 2-(3,5-dimethylpyrazol-1-yl)ethylseleno derivatives and their probable glutathione peroxidase (GPx) like activity
  作者：Ananda S. Hodage、Prasad P. Phadnis、Amey Wadawale、K. I. Priyadarsini、Vimal K. Jain

  DOI：10.1039/c0ob00807a

  日期：——

  A series of 2-(3,5-dimethylpyrazol-1-yl)ethylseleno derivatives has been synthesized. The glutathione peroxidase like catalytic activity of these compounds has been studied in a model system, in which reduction of hydrogen peroxide with dithiothreitol (DTTred), in the presence of an organoselenium compound was investigated by 1H NMR spectroscopy. All these compounds exhibit GPx like catalytic activities and the catalytic reaction proceeds through a selenoxide intermediate, identified by 77Se1H} NMR spectroscopy.

  合成了一系列2-(3,5-二甲基吡唑-1-基)乙基硒衍生物。研究了这些化合物在模型系统中的谷胱甘肽过氧化物酶样催化活性，其中利用有机硒化合物存在下，用二硫苏糖醇（DTTred）还原过氧化氢，通过1H NMR光谱进行研究。所有这些化合物均表现出GPx样催化活性，催化反应通过一种硒氧化物中间体进行，该中间体由77Se1H} NMR光谱鉴定。
• [EN] PHENETHANOLAMINE DERIVATIVE FOR THE TREATMENT OF RESPIRATORY DISEASES<br/>[FR] DERIVE DE PHENETHANOLAMINE UTILISE DANS LE TRAITEMENT DE MALADIES RESPIRATOIRES
  申请人：GLAXO GROUP LTD

  公开号：WO2004037773A1

  公开（公告）日：2004-05-06

  The present invention relates to novel compounds of formula (I), to a process for their manufacture, to pharmaceutical compositions containing them, and to their use in therapy, in particular their use in the prophylaxis and treatment of respiratory diseases.

  本发明涉及公式（I）的新化合物，以及其制备方法、含有它们的药物组合物，以及它们在治疗中的使用，特别是在预防和治疗呼吸道疾病中的使用。
• Natural products-based insecticidal agents 11. Synthesis and insecticidal activity of novel 4α-arylsulfonyloxybenzyloxy-2β-chloropodophyllotoxin derivatives against Mythimna separata Walker in vivo
  作者：Hui Xu、Jun-Liang Zhang

  DOI：10.1016/j.bmcl.2011.07.075

  日期：2011.9

  In continuation of our program aimed at the discovery and development of natural products-based insecticidal agents, 14 novel 4 alpha-arylsulfonyloxybenzyloxy-2 beta-chloropodophyllotoxin derivatives were stereoselectively semisynthesized from podophyllotoxin, and preliminarily evaluated for their insecticidal activity against the pre-third-instar larvae of Mythimna separata Walker in vivo. Especially compounds 9c' and 9g' exhibited the most promising and pronounced insecticidal activity than toosendanin, a commercial insecticide derived from Melia azedarach at 1 mg/mL. Generally, it was preliminarily demonstrated that arylsulfonyloxy groups at the C-2 position of benzyloxy moiety and the length of the side chain on the benzenesulfonyloxy group of 4 alpha-arylsulfonyloxybenzyloxy-2 beta-chloropodophyllotoxins might be important for the insecticidal activity. (C) 2011 Elsevier Ltd. All rights reserved.