2-(thiomorpholinomethyl)phenol | 151291-55-3

• 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-(thiomorpholinomethyl)phenol
• 英文别名: 2-(thiomorpholin-1-ylmethyl)phenol；2-(Thiomorpholin-4-ylmethyl)phenol
• CAS: 151291-55-3
• 化学式: C₁₁H₁₅NOS
• 分子量: 209.312
• InChiKey: XWCBLEYDANLDPN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  48.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-(Methoxymethyl)thiomorpholine 、 苯酚 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以90%的产率得到2-(thiomorpholinomethyl)phenol
  参考文献：
  名称：

  布朗斯台德酸催化苯酚的化学和邻位选择性氨甲基化

  摘要：

  我们开发了一种布朗斯台德酸催化的游离酚的高度邻位选择性官能化，在温和条件下易于获得N，O-缩醛，以中等至优异的产率提供各种相应的氨甲基化苯酚产品。这种转化的显着特点包括条件温和、底物范围好、邻位选择性好、效率高、易于进一步转化。

  DOI：

  10.1039/d1ob00820j

文献信息

• Regioselective Mannich Reaction of Phenols under High Pressure Using Dichloromethane as C1 Unit
  作者：Kiyoshi Matsumoto、Kouta Joho、Seisuke Mimori、Hirokazu Iida、Hiroshi Hamana、Akikazu Kakehi

  DOI：10.3987/com-08-s(n)111

  日期：——

  Regioselectivity in Mannich reaction of 4-, 3-, and 2-substituted phenols with typical heterocyclic amines are investigated under reaction conditions developed by Lis. Phenol and 4-alkyl, and 4-chlorophenols in the title reaction predominantly gave the corresponding 2-(aminometllyl)phenols, while 4-methoxyphenol afforded, in addition to the mono(aminomethyl) phenols, a considerable amount of the bis adducts. Peculiarly enough, 3-methylphenol with amines afforded 3-methyl-4-(aminomethyl) phenols whereas 2-methylphenol produced 2-methyl-6-(aminomethyl)phenols.
• Deprotonation Mechanism and log <i>P</i> Values of New Antihypertensive Thiomorpholinylmethylphenols: A Combined Experimental and Theoretical Study
  作者：Karla Sanpedro-Montoya、Beatriz Martínez-Pérez、Annia Galano、Enrique Ángeles、Víctor H. Abrego、María Teresa Ramírez-Silva、Alberto Rojas-Hernández

  DOI：10.1021/je100470g

  日期：2010.10.14

  Four new antihypertensive thiomorpholinylmethylphenol compounds were synthesized by its potential antihypertensive and antiarhythmic properties. The pK(a) values were determined experimentally, with die aid of program SQUAD, by Capillary Zone Electrophoresis (CZE) (T = 310.15 K and / = 0.05 mol.dm(-3)) and by UV spectrophotometry at pseudophysiological conditions (T = 310.15 K and / = 0.15 mol.dm(-3)). obtaining good agreement between the values determined with both techniques. A theoretical study was followed to propose a deprotonation mechanism for each compound. The log P values were also determined between n-octanol and water and compared with the values of other similar compounds to relate it with its possible biological activity.
• Brønsted acid catalysed chemo- and <i>ortho</i>-selective aminomethylation of phenol
  作者：Zhiqiong Tang、Dongdong Li、Yidi Yue、Dan Peng、Lu Liu

  DOI：10.1039/d1ob00820j

  日期：——

  We have developed a Brønsted acid catalysed highly ortho-selective functionalization of free phenols with readily available N,O-acetals under mild conditions, furnishing various corresponding aminomethylated phenol products in moderate to excellent yields. The salient features of this transformation include mild conditions, good substrate scope, excellent ortho-selectivity, high efficiency, and ease

  我们开发了一种布朗斯台德酸催化的游离酚的高度邻位选择性官能化，在温和条件下易于获得N，O-缩醛，以中等至优异的产率提供各种相应的氨甲基化苯酚产品。这种转化的显着特点包括条件温和、底物范围好、邻位选择性好、效率高、易于进一步转化。