4-(吗啉-4-磺酰基)-苯酚 | 3077-65-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-(吗啉-4-磺酰基)-苯酚
• 中文别名: D-阿卓糖酮酸
• 英文名称: 4-(morpholinosulfonyl)phenol
• 英文别名: 4-(Morpholin-4-ylsulfonyl)phenol；4-morpholin-4-ylsulfonylphenol
• CAS: 3077-65-4
• 化学式: C₁₀H₁₃NO₄S
• mdl: MFCD03147214
• 分子量: 243.284
• InChiKey: LYIHIMLRHVZNJK-UHFFFAOYSA-N

物化性质

• 熔点：
  149-151 °C
• 沸点：
  437.7±55.0 °C(Predicted)
• 密度：
  1.396±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  75.2
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 海关编码：
  2935009090
• 危险性防范说明：
  P261,P264,P270,P271,P280,P301+P312,P302+P352,P304+P340,P305+P351+P338,P330,P332+P313,P337+P313,P362,P403+P233,P405,P501
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  (R)-2-氯-1-(2-甲基环氧乙烷-2-基甲基)-4-硝基咪唑 、 4-(吗啉-4-磺酰基)-苯酚 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以28%的产率得到(R)-2-{4-(morpholinsulfonyl)phenoxymethyl}-2,3-dihydro-2-methyl-6-nitroimidazo[2,1-b]oxazole
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Polar Functionalities Containing Nitrodihydroimidazooxazoles as Anti-TB Agents

  摘要：

  Novel polar functionalities containing 6-nitro-2,3-dihydroimidazooxazole (NHIO) analogues were synthesized to produce a compound with enhanced solubility. Polar functionalities including sulfonyl, uridyl, and thiouridyl-bearing NHIO analogues were synthesized and evaluated against Mycobacterium tuberculosis (MTB) H(37)Rv. The aqueous solubility of compounds with MIC values <= 0.5 mu g/mL were tested, and six compounds showed enhanced aqueous solubility. The best six compounds were further tested against resistant (Rif(R) and MDR) and dormant strains of MTB and tested for cytotoxicity in HepG2 cell line. Based on its overall in vitro characteristics and solubility profile, compound 6d was further shown to possess high microsomal stability, solubility under all tested biological conditions (PBS, SGF and SIF), and favorable oral in vivo pharmacokinetics and in vivo efficacy.

  DOI：

  10.1021/acsmedchemlett.5b00202
• 作为产物：
  描述：

  4-羟基苯磺酰氯 在 甲醇 、 三乙胺 作用下， 以 氯仿 为溶剂， 反应 12.0h， 生成 4-(吗啉-4-磺酰基)-苯酚
  参考文献：
  名称：

  Practical Sulfonylation of Amines with 4‐Hydroxybenzenesulfonyl Chloride: In Situ Silylation–Desilylation

  摘要：

  A one-pot procedure for the efficient sulfonylation of amines with 4-hydroxybenzenesulfonyl chloride involving in situ protection and deprotection of the phenol with N,O-bis(trimethylsilyl)acetamide (BTSA) is presented.

  DOI：

  10.1081/scc-200026214

文献信息

• One-Pot Sulfonamide Synthesis Exploiting the Palladium-Catalyzed Sulfination of Aryl Iodides
  作者：Michael Willis、Emmanuel Flegeau、Jack Harrison

  DOI：10.1055/s-0035-1560578

  日期：——

  prepared from aryl iodides and the sulfur dioxide surrogate DABSO, under the action of a palladium(0) catalyst, are transformed in a one-pot process to a variety of functionalized sulfonamides. The sulfinate to sulfonamide transformation is achieved by simple treatment with an aqueous solution of the relevant amine and sodium hypochlorite (bleach). A broad range of amines, including anilines, and amino

  芳基亚磺酸铵，方便地由芳基碘化物和二氧化硫替代物 DABSO 制备，在钯 (0) 催化剂的作用下，在一锅法中转化为各种功能化的磺酰胺。亚磺酸盐向磺酰胺的转化是通过用相关胺和次氯酸钠（漂白剂）的水溶液进行简单处理来实现的。广泛的胺，包括苯胺和氨基酸衍生物，可与各种芳基碘有效结合，产生高产率的磺胺类药物。
• S(<scp>vi</scp>) in three-component sulfonamide synthesis: use of sulfuric chloride as a linchpin in palladium-catalyzed Suzuki–Miyaura coupling
  作者：Xuefeng Wang、Min Yang、Shengqing Ye、Yunyan Kuang、Jie Wu

  DOI：10.1039/d1sc01351c

  日期：——

  Sulfuric chloride is used as the source of the –SO2– group in a palladium-catalyzed three-component synthesis of sulfonamides. Suzuki–Miyaura coupling between the in situ generated sulfamoyl chlorides and boronic acids gives rise to diverse sulfonamides in moderate to high yields with excellent reaction selectivity. Although this transformation is not workable for primary amines or anilines, the results

  在钯催化的三组分磺酰胺合成中，氯化硫被用作-SO 2-基团的来源。原位生成的氨磺酰氯与硼酸之间的Suzuki-Miyaura偶联以中等至高收率产生了多种磺酰胺，并具有出色的反应选择性。尽管此转化不适用于伯胺或苯胺，但结果表明官能团耐受性高。通过解决脱磺酰化问题并利用廉价且容易获得的氯化硫作为二氧化硫的来源，首先实现了氧化还原中性三组分合成的磺酰胺。
• A Broad‐Spectrum Catalytic Amidation of Sulfonyl Fluorides and Fluorosulfates**
  作者：Mingjie Wei、Dacheng Liang、Xiaohui Cao、Wenjun Luo、Guojian Ma、Zeyuan Liu、Le Li

  DOI：10.1002/anie.202013976

  日期：2021.3.22

  A broad‐spectrum, catalytic method has been developed for the synthesis of sulfonamides and sulfamates. With the activation by the combination of a catalytic amount of 1‐hydroxybenzotriazole (HOBt) and silicon additives, amidations of sulfonyl fluorides and fluorosulfates proceeded smoothly and excellent yields were generally obtained (87–99 %). Noticeably, this protocol is particularly efficient for

  已经开发了一种广谱催化方法，用于合成磺酰胺和氨基磺酸盐。通过催化量的1-羟基苯并三唑（HOBt）和硅添加剂的结合活化，磺酰氟和氟代硫酸盐的酰胺化反应顺利进行，通常获得优异的收率（87–99％）。值得注意的是，该协议对于空间受阻的底物特别有效。催化剂的负载量通常很低，而金刚烷衍生物的十克级合成仅需要0.02 mol％的催化剂。此外，通过关键中间体磺酰氟13合成市售药物Fedratinib，已证明了该方法在药物化学中的潜力。。由于大量的胺是可商购的，因此该途径提供了进入Fedratinib类似物进行生物学筛选的简便途径。
• SUBSTITUTED AMINOINDANES AND ANALOGS THEREOF, AND THE PHARMACEUTICAL USE THEREOF
  申请人：Rackelmann Nils

  公开号：US20110201590A1

  公开（公告）日：2011-08-18

  The invention relates to substituted aminoindanes and analogs thereof of formula (I) and the pharmaceutical use thereof. Medicaments which comprise compounds of this type are suitable for the prevention or treatment of diverse disorders such as, for example, of respiratory disorders, cystic fibrosis disorders, acute or chronic renal disorders or bowel disorders.

  该发明涉及公式（I）的替代氨基茚和类似物及其药用。包含这类化合物的药物适用于预防或治疗各种疾病，例如呼吸系统疾病、囊性纤维化疾病、急性或慢性肾脏疾病或肠道疾病。
• Derivatives of p-guantidinobenzoic acid and pharmaceutical agents
  申请人：Ono Pharmaceutical Co., Ltd.

  公开号：US04843094A1

  公开（公告）日：1989-06-27

  Compounds presented by the general formula: ##STR1## [wherein when Y is oxygen, R.sup.2 is H, alkyl, alkoxy, alkoxymethyl, --COOR.sup.3, --CH.sub.2 COOR.sup.3, --CH.dbd.CH--COOR.sup.3, halogen, --CF.sub.3, --COR.sup.4, --OCOR.sup.4, --CH.sub.2 OCOR.sup.4, --SO.sub.2 R.sup.4, --OSO.sub.2 R.sup.4, --CONR.sup.5 R.sup.6, --SO.sub.2 NR.sup.5 R.sup.6, --CONH--SO.sub.2 NR.sup.5 R.sup.6, --NHSO.sub.2 R.sup.7, --NO.sub.2, --OH, --CH.sub.2 OH, guanidino, benzyloxy, guanidinophenylthiomethyl, morpholinosulfonylphenoxymethyl, pyridyloxymethyl, or (1,1-dioxothiazol-3-yl)carbonyl, or when Y is sulfur, R.sup.2 is H, alkyl, alkoxy, halogen, --COOR.sup.3, --CH.sub.2 COOR.sup.3, --NO.sub.2, or --SO.sub.2 NR.sup.5 R.sup.6, and n represents an integer of one to five, and when n represents more than two, each of R.sup.2 may be the same group or the different group.] and acid addition salts thereof have inhibitory effect on elastase, and, therefore, are useful for the treatment and/or prevention of diseases induced by abnormal enhancing of degradation of proteins such as elastin and the like, by the action of elastase in mammals, especially in human beings.

  通式为：##STR1##的化合物及其酸盐具有对弹性蛋白酶的抑制作用，因此对于治疗和/或预防由于蛋白质降解异常增强引起的疾病，如弹性蛋白等在哺乳动物中，特别是在人类中的作用是有用的。