1-(chloromethoxy)-2-(methylsulfonyl)ethane | 129499-56-5

• 分子结构分类: 有机化合物 - 有机硫化合物 - 磺酰类
• 英文名称: 1-(chloromethoxy)-2-(methylsulfonyl)ethane
• 英文别名: 2-(methylsulfonyl)ethoxymethyl chloride；MeSO2(CH2)2OCH2Cl；MeSO2CH2CH2OCH2Cl；Msem-Cl；1-(Chloromethoxy)-2-methylsulfonylethane
• CAS: 129499-56-5
• 化学式: C₄H₉ClO₃S
• 分子量: 172.633
• InChiKey: DDWYEYWVLLCMFO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(chloromethoxy)-2-(methylsulfonyl)ethane 、 2-(二甲氧基甲基)-1H-咪唑 在 sodium hydride 作用下， 生成
  参考文献：
  名称：

  Quaternary salts of 2-[(hydroxyimino)methyl]imidazole. 5. Structure-activity relationships for side-chain nitro-, sulfone-, amino-, and aminosulfonyl-substituted analogs for therapy against anticholinesterase intoxication

  摘要：

  Several quaternary imidazolium oxime derivatives incorporating side chains bearing nitro, sulfone, amino, and aminosulfonyl substituents were prepared and evaluated as treatment therapeutics for anti-AChE intoxication. In vivo test results in the mouse revealed that many of these compounds are highly effective in providing life-saving protection against the extremely toxic cholinesterase inhibitors soman and tabun. Several structure-activity relationships were noted that were characteristic of the side-chain substituent. In vivo test results for additional selected derivatives of some of the more therapeutically active compounds indicated that the quaternary heteroaryl nucleus is essential for activity whereas a nucleophilic moiety (i.e., oxime) is not. In support of previous suspicions, these results afforded additional evidence suggesting that reactivation is not the main mode of antidotal action by the imidazolium oximes. An alternative antidotal mechanism is postulated that is consistent with all data and that involves enzyme protection by the compounds.

  DOI：

  10.1021/jm00108a020
• 作为产物：
  描述：

  MeSO2(CH2)2OCH2SCH3 在 磺酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以100%的产率得到1-(chloromethoxy)-2-(methylsulfonyl)ethane
  参考文献：
  名称：

  The methylsulfonylethoxymethyl (Msem) as a hydroxyl protecting group in oligosaccharide synthesis

  摘要：

  The methylsulfonylethoxymethyl (Msem) is introduced as a base-labile, non-participating protecting group in carbohydrate chemistry. Conditions to introduce the Msem on primary and secondary alcohols are described. Removal of the Msem is best achieved using a catalytic amount of tetrabutylammonium fluoride (TBAF), with or without a nucleophilic scavenger. Applicability of the Msem group is illustrated in the assembly of an all 1,3-cis-linked mannotrioside. (c) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.06.007

文献信息

• GOFF, DANE A.;KOOLPE, GARY A.;KELSON, ANDREW B.;VU, HUYNH M.;TAYLOR, DORR+, J. MED. CHEM., 34,(1991) N, C. 1363-1366
  作者：GOFF, DANE A.、KOOLPE, GARY A.、KELSON, ANDREW B.、VU, HUYNH M.、TAYLOR, DORR+

  DOI：——

  日期：——
• Quaternary salts of 2-[(hydroxyimino)methyl]imidazole. 5. Structure-activity relationships for side-chain nitro-, sulfone-, amino-, and aminosulfonyl-substituted analogs for therapy against anticholinesterase intoxication
  作者：Gary A. Koolpe、Steven M. Lovejoy、Dane A. Goff、Kuei Ying Lin、Doris S. Leung、Clifford D. Bedford、Ralph N. Harris、H. A. Musallam、Irwin Koplovitz

  DOI：10.1021/jm00108a020

  日期：1991.4

  Several quaternary imidazolium oxime derivatives incorporating side chains bearing nitro, sulfone, amino, and aminosulfonyl substituents were prepared and evaluated as treatment therapeutics for anti-AChE intoxication. In vivo test results in the mouse revealed that many of these compounds are highly effective in providing life-saving protection against the extremely toxic cholinesterase inhibitors soman and tabun. Several structure-activity relationships were noted that were characteristic of the side-chain substituent. In vivo test results for additional selected derivatives of some of the more therapeutically active compounds indicated that the quaternary heteroaryl nucleus is essential for activity whereas a nucleophilic moiety (i.e., oxime) is not. In support of previous suspicions, these results afforded additional evidence suggesting that reactivation is not the main mode of antidotal action by the imidazolium oximes. An alternative antidotal mechanism is postulated that is consistent with all data and that involves enzyme protection by the compounds.
• The methylsulfonylethoxymethyl (Msem) as a hydroxyl protecting group in oligosaccharide synthesis
  作者：Asghar Ali、Richard J.B.H.N. van den Berg、Herman S. Overkleeft、Gijsbert A. van der Marel、Jeroen D.C. Codée

  DOI：10.1016/j.tet.2010.06.007

  日期：2010.8

  The methylsulfonylethoxymethyl (Msem) is introduced as a base-labile, non-participating protecting group in carbohydrate chemistry. Conditions to introduce the Msem on primary and secondary alcohols are described. Removal of the Msem is best achieved using a catalytic amount of tetrabutylammonium fluoride (TBAF), with or without a nucleophilic scavenger. Applicability of the Msem group is illustrated in the assembly of an all 1,3-cis-linked mannotrioside. (c) 2010 Elsevier Ltd. All rights reserved.