2-{[(4-methylphenyl)sulfonyl]oxy} ethyl acetate | 19859-09-7

• 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-{[(4-methylphenyl)sulfonyl]oxy} ethyl acetate
• 英文别名: 2-(p-toluenesulfonyloxy) ethyl acetate；Ethylenglycolacetattosylat；2-(4-Methylphenyl)sulfonyloxyethyl acetate
• CAS: 19859-09-7
• 化学式: C₁₁H₁₄O₅S
• 分子量: 258.295
• InChiKey: OZXXZGAAZOLRHK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  78
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-溴-3-甲基噻吩 、 2-{[(4-methylphenyl)sulfonyl]oxy} ethyl acetate 在 magnesium 作用下， 以 乙醚 为溶剂， 生成 acetic acid 2-(3-methyl-thiophen-2-yl)-ethyl ester
  参考文献：
  名称：

  Orally active aminopyridines as inhibitors of tetrameric fructose-1,6-bisphosphatase

  摘要：

  A novel sulfonylureido pyridine series exemplified by compound 19 yielded potent inhibitors of FBPase showing significant glucose reduction and modest glycogen lowering in the acute db/db mouse model for Type-2 diabetes. Our inhibitors occupy the allosteric binding site and also extend into the dyad interface region of tetrameric FBPase. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.04.044
• 作为产物：
  描述：

  环氧乙烷 、 对甲基苯磺酸乙酸酐 生成 2-{[(4-methylphenyl)sulfonyl]oxy} ethyl acetate
  参考文献：
  名称：

  Mixed sulfonic-carboxylic anhydrides. II. Reactions with aliphatic ethers and amines

  摘要：

  DOI：

  10.1021/jo00803a010

文献信息

• 1,3-Dioxolan-2-ylium cations from acylfurans: Conversion of furyl ketones to esters under nonoxidative conditions
  作者：John A. Bender、Samantha Daves、F.G. West

  DOI：10.1016/s0040-4039(98)00185-3

  日期：1998.4

  Acylfurans 3 furnished tosylated glycol monoesters 5 when treated with 1,2-diols in the presence of an equivalent of TsOH. This process likely occurs via protiodefuranation of the intermediate furyl ketals to form 1,3-dioxolan-2-ylium cations 8. Subsequent ring-opening via SN2 nucleophilic displacement by p-toluenesulfonate then provides esters 5. When a 1,3-diol was employed, furan-containing ester

  当在等价的TsOH存在下用1,2-二醇处理时，酰基呋喃3提供了甲苯磺酸化的二醇单酯5。此过程可能通过中间呋喃基缩酮的Protoodefuranation形成1，3-dioxolan-2-ylium阳离子8发生。随后通过对甲苯磺酸的S N 2亲核取代而开环，然后提供酯5。当使用1，3-二醇时，通过表观的醇醛二聚/片段化途径形成了含呋喃的酯9而不是标准产物。
• Deacylation of pyrrole and other aromatic ketones
  作者：M. W. Moon、R. A. Wade

  DOI：10.1021/jo00189a002

  日期：1984.7
• Auteri,S.C. et al., Australian Journal of Chemistry, 1977, vol. 30, p. 2479 - 2485
  作者：Auteri,S.C. et al.

  DOI：——

  日期：——
• MOON, M. W.;WADE, R. A., J. ORG. CHEM., 1984, 49, N 15, 2663-2669
  作者：MOON, M. W.、WADE, R. A.

  DOI：——

  日期：——
• Orally active aminopyridines as inhibitors of tetrameric fructose-1,6-bisphosphatase
  作者：Paul Hebeisen、Wolfgang Haap、Bernd Kuhn、Peter Mohr、Hans Peter Wessel、Ulrich Zutter、Stephan Kirchner、Armin Ruf、Jörg Benz、Catherine Joseph、Rubén Alvarez-Sánchez、Marcel Gubler、Brigitte Schott、Agnes Benardeau、Effie Tozzo、Eric Kitas

  DOI：10.1016/j.bmcl.2011.04.044

  日期：2011.6

  A novel sulfonylureido pyridine series exemplified by compound 19 yielded potent inhibitors of FBPase showing significant glucose reduction and modest glycogen lowering in the acute db/db mouse model for Type-2 diabetes. Our inhibitors occupy the allosteric binding site and also extend into the dyad interface region of tetrameric FBPase. (C) 2011 Elsevier Ltd. All rights reserved.