(mesyloxy)acetic acid | 3586-50-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: (mesyloxy)acetic acid
• 英文别名: Carboxymethyl methanesulfonate；2-methylsulfonyloxyacetic acid
• CAS: 3586-50-3
• 化学式: C₃H₆O₅S
• 分子量: 154.144
• InChiKey: RRFDQGMDVFAAGT-UHFFFAOYSA-N

物化性质

• 熔点：
  113-114 °C
• 沸点：
  390.1±25.0 °C(Predicted)
• 密度：
  1.540±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  89
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 海关编码：
  2915900090

反应信息

• 作为反应物：
  描述：

  (mesyloxy)acetic acid 在 氯化亚砜 作用下， 生成 (mesyloxy)acetyl chloride
  参考文献：
  名称：

  Havbrandt,O.; Wachtmeister,C.A., Acta Chemica Scandinavica (1947), 1968, vol. 22, p. 2043 - 2044

  摘要：

  DOI：
• 作为产物：
  描述：

  (mesyloxy)acetonitrile 在 硫酸 、 水 作用下， 反应 0.33h， 以75%的产率得到(mesyloxy)acetic acid
  参考文献：
  名称：

  β-Lactams fromD-Erythrose-Derived Imines: A Convenient Synthesis of 2,3-Diamino-2,3-dideoxy-D-mannonic-Acid Derivatives

  摘要：

  The D-manno-configured N-anisylated beta-lactam 40, the beta-lactam carboxylic acids 4 and 43, and the corresponding phosphonic-acid isosters 49 and 50 have been synthesized from D-glucose in 8-10 steps, respectively None of these compounds exhibited a significant inhibitory activity in vitro against the sialidases of Vibrio cholerae, Salmonella typhimurium, Influenza A (N9), and Influenza B virus. Cycloaddition of the in situ generated imines derived from the D-erythroses 6, 16, and 17 with the ketene: from mesyloxyacetyl chloride (20) gave the 2-mesyloxy-D-hexono-1,3-lactams 25, 27a/b, 28a/b/c, and 29 in 23, 69, 57, and 90% yield, respectively (Scheme 3). Transformation of 27a/b and 29 (> 85%) to the corresponding azides, followed by oxidative N-deprotection, gave 30a/b (45%) and 34 (80%). Subsequent alkylation of the ring N-atom in 31a with benzyl bromoacetate and dibenzyl (triflyloxymethyl)phosphonate 46 gave the carboxylate 41 (77%) and the phosphonate 47 (55%; Schemes 4 and 5). Hydrogenolysis of 41 gave the beta-lactam amino acid 43, besides its hydrolysis product 44. Reductive N-acylation of the azido group in 41 (93%), followed by hydrogenolytic debenzylation, yielded the 2-trifluoroacetamido N-(carboxymethyl)-beta-lactam 4 (56%). Similarly, 47 gave the 2-trifluoroacetamide 48 (89%), and hence, the 2-amino-N-(phosphonoylmethyl)-beta-lactams 49 (40%) and 50, resulting from deacylation of 49 (14%). Aminolysis and carbamoylation of the protected beta-lactams 31a and 35 led to the 2,3-diamino-2,3-dideoxy-D-mannonamides 51 and 53, respectively (Scheme 6).

  DOI：

  10.1002/(sici)1522-2675(19991215)82:12<2380::aid-hlca2380>3.0.co;2-p

文献信息

• Synthesis and Radiofluorination of Iodophenyl Esters as Tool for the Traceless Staudinger Ligation
  作者：Marc Pretze、Anke Flemming、Martin Kockerling、Constantin Mamat

  DOI：10.1515/znb-2010-0912

  日期：2010.9.1

  A new synthetic pathway for the preparation of ω-functionalized 2-iodophenyl esters as starting materials for the synthesis of substituted phosphanes is described. A radiolabeling of these esters with fluorine-18 has led to building blocks which were reacted with HPPh₂ in a Pd-catalyzed P-C cross coupling to establish new phosphanes. These compounds can be applied as mild and bioorthogonal radiolabeling agents by means of the traceless Staudinger ligation. A route to access this class of compounds has been established.

  描述了一种新的合成途径，用于制备ω-官能化的2-碘苯酯，作为合成取代膦烷的起始物。将这些酯与氟-18进行放射标记，得到的构建块与HPPh₂在Pd催化的P-C交叉偶联中反应，建立了新的膦烷。通过无痕Staudinger缩合，这些化合物可以作为温和且生物正交的放射标记试剂。已建立了访问这类化合物的途径。
• Inactivation of liver alcohol dehydrogenases and inhibition of ethanol metabolism by ambivalent active-site-directed reagents
  作者：Wen-Sherng Chen、David P. Bohlken、Bryce V. Plapp

  DOI：10.1021/jm00134a012

  日期：1981.2

  Active-site-directed reagents, of the general structure omega-(BrCH2CONH)RCOY, where R = alkyl, aryl, or aralkyl, and Y = OH or NH2, inactivated horse, mouse, rat, and human liver alcohol dehydrogenases at widely different rates, reflecting differences in reagent specificity and in the structures of the enzymes. Treatment of mice and rats with either of two optimally specific reagents, p-(XCH2CONH)C6H4(CH2)3CONH2

  活性定点的通用结构为omega-（Br CONH）RCOY的试剂，其中R =烷基，芳基或芳烷基，Y = OH或NH2，失活的马，小鼠，大鼠和人肝醇脱氢酶有很大不同速率，反映了试剂特异性和酶结构的差异。用两种最佳特异性试剂p-（X CONH）C6H4（CH2）3CONH2（其中X = Br（7）或CH3SO3（10））部分（20％至40％）灭活肝脏中的酒精脱氢酶对小鼠和大鼠进行治疗，抑制乙醇代谢，并延长乙醇在这些动物体内产生的协调性受损。尽管使用的7种剂量（0.13 mmol / kg）接近LD50，但10种有效剂量为0.48 mmol / kg，无急性毒性。
• Versuche zur Totalsynthese von Cephalosporinderivaten, I Darstellung vontrans-3-Sulfonyloxy-4-alkylthio-2-azetidinonen
  作者：Rudolf Lattrell、Gerhard Lohaus

  DOI：10.1002/jlac.197419740605

  日期：1974.7.26

  Sulfonyloxyacetylchloride 1 reagieren mit Thioimidsäureestern 2 in Gegenwart von Triäthylamin zu trans-3-Sulfonyloxy-4-alkylthio-2-azetidinonen 3. Ein weiterer Weg zu dieser neuen Klasse von β-Lactamderivaten besteht in der Reaktion von Acyloxyacetylchloriden 8 mit Thioimidsäureestern 2, Verseifung der gebildeten 3-Acyloxy-2-azetidinone 9 zu den 3-Hydroxyverbindungen 10 und deren Veresterung mit Sulfonsäurechloriden

  在三乙胺的存在下，磺酰氧基乙酰氯1与硫代酰亚胺酯2反应形成反式-3-磺酰氧基-4-烷基硫基-2-氮杂环丁酮3。这类新的β-内酰胺衍生物的另一种途径是酰氧基乙酰氯8与硫代亚磺酸酯2的反应，3-酰氧基-2-氮杂环丁烷酮9的皂化反应，生成3-羟基化合物10以及它们与磺酸的酯化反应。酰氯。所示的β-内酰胺中硫和氮的不饱和残基被臭氧氧化形成羰基官能团。的Δ反应2 -thiazolines和5,6-二氢-4-氧代描述了H -1，3-噻嗪与磺酰氧基乙酰氯形成双环β-内酰胺衍生物。
• Phan; Miskolczi; Sztaricskai, Acta Chimica Academiae Scientiarum Hungaricae, 1980, vol. 103, # 4, p. 415 - 420
  作者：Phan、Miskolczi、Sztaricskai、Bognar

  DOI：——

  日期：——