2-(methylsulfonyl)acetaldehyde | 13154-68-2

• 分子结构分类: 有机化合物 - 有机硫化合物 - 磺酰类
• 英文名称: 2-(methylsulfonyl)acetaldehyde
• 英文别名: methanesulfonyl-acetaldehyde；(Methanesulfonyl)acetaldehyde；2-methylsulfonylacetaldehyde
• CAS: 13154-68-2
• 化学式: C₃H₆O₃S
• 分子量: 122.145
• InChiKey: QAKXPQSVKFRFHD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  7
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  59.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  {4-[4-(2-Methyl-quinolin-4-ylmethoxy)-benzoylamino]-piperidin-4-yl}-acetic acid methyl ester 、 2-(methylsulfonyl)acetaldehyde 在 三乙酰氧基硼氢化钠 作用下， 以 1,2-二氯乙烷 为溶剂， 生成 {1-(2-Methanesulfonyl-ethyl)-4-[4-(2-methyl-quinolin-4-ylmethoxy)-benzoylamino]-piperidin-4-yl}-acetic acid methyl ester
  参考文献：
  名称：

  Synthesis and structure–activity relationship of a novel, achiral series of TNF-α converting enzyme inhibitors

  摘要：

  A novel series of achiral TNF-alpha converting enzyme (TACE) inhibitors has been discovered. These compounds exhibited activities from 0.35 to 11 nM in a porcine TACE assay and inhibited TNF-alpha production in an LPS-stimulated whole blood assay with an IC50 value of 23 nM for the most potent one. They also have excellent selectivities over related metalloproteases including aggrecanases. (C) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.02.015
• 作为产物：
  描述：

  2,2'-bis-methanesulfonyl-1,1'-oxy-bis-ethanol 120.0 ℃ 、1.33 Pa 条件下， 生成 2-(methylsulfonyl)acetaldehyde
  参考文献：
  名称：

  Wanzlick,H.-W.; Ahrens,H., Chemische Berichte, 1966, vol. 99, p. 1580 - 1588

  摘要：

  DOI：

文献信息

• NITROGENOUS HETEROCYCLIC COMPOUND, PREPARATION METHOD, INTERMEDIATE, COMPOSITION AND USE
  申请人：Shanghai Pharmaceuticals Holding Co., Ltd.

  公开号：EP3424928A1

  公开（公告）日：2019-01-09

  Disclosed are a nitrogenous heterocyclic compound, intermediates, a preparation method, a composition and use thereof. The nitrogenous heterocyclic compound in the present invention is as shown in formula I. The compound has a high inhibitory activity towards ErbB2 tyrosine kinase and a relatively good inhibitory activity towards human breast cancer BT-474 and human gastric cancer cell NCI-N87 which express ErbB2 at a high level, and at the same time has a relatively weak inhibitory activity towards EGFR kinase. Namely, the compound is a highly selective small-molecule inhibitor targeted at ErbB2, and hence it has a high degree of safety, and can effectively enlarge the safety window in the process of taking the drug.

  本公开揭示了一种含氮杂环化合物、中间体、制备方法、组合物及其用途。本发明中的含氮杂环化合物如公式I所示。该化合物对ErbB2酪氨酸激酶具有较高的抑制活性，并且对人类乳腺癌BT-474和人类胃癌细胞NCI-N87表达ErbB2的抑制活性相对较好，同时对EGFR激酶具有相对较弱的抑制活性。换句话说，该化合物是一种高度选择性的针对ErbB2的小分子抑制剂，因此具有很高的安全度，并且可以有效地扩大服药过程中的安全窗口。
• Eliminative fission of hydroxythietanes: transition structures for cleavage of 4-membered rings
  作者：David J. Young、Charles J. M. Stirling

  DOI：10.1039/c39870000552

  日期：——

  Pathways in nucleophilic fission of hydroxythietanes are determined by the oxidation state of sulphur; for eliminative fission, activation parameters, substituent effects, and comparison with unstrained analogues all suggest a greater degree of ring cleavage in the transition structure for thietanes than for cyclobutanes.

  羟基硫杂环丁烷亲核裂变的途径由硫的氧化态决定。对于消除裂变，活化参数，取代基作用以及与未拉伸的类似物的比较均表明，硫杂环丁烷比环丁烷在过渡结构中的环裂解程度更高。
• Diggle, Andrew W.; Griffiths, Gwerydd; Young, David J., Bulletin de la Societe Chimique de France, 1988, # 2, p. 317 - 321
  作者：Diggle, Andrew W.、Griffiths, Gwerydd、Young, David J.、Stirling, Charles J. M.

  DOI：——

  日期：——
• Synthesis and structure–activity relationship of a novel, achiral series of TNF-α converting enzyme inhibitors
  作者：John L. Gilmore、Bryan W. King、Cathy Harris、Thomas Maduskuie、Stephen E. Mercer、Rui-Qin Liu、Maryanne B. Covington、Mingxin Qian、Maria D. Ribadeneria、Krishna Vaddi、James M. Trzaskos、Robert C. Newton、Carl P. Decicco、James J.-W. Duan

  DOI：10.1016/j.bmcl.2006.02.015

  日期：2006.5

  A novel series of achiral TNF-alpha converting enzyme (TACE) inhibitors has been discovered. These compounds exhibited activities from 0.35 to 11 nM in a porcine TACE assay and inhibited TNF-alpha production in an LPS-stimulated whole blood assay with an IC50 value of 23 nM for the most potent one. They also have excellent selectivities over related metalloproteases including aggrecanases. (C) 2006 Elsevier Ltd. All rights reserved.
• Wanzlick,H.-W.; Ahrens,H., Chemische Berichte, 1966, vol. 99, p. 1580 - 1588
  作者：Wanzlick,H.-W.、Ahrens,H.

  DOI：——

  日期：——