O-ethyl S-4-methoxy-4-oxo-1-phthalimidomethylbutyl dithiocarbonate | 479421-16-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: O-ethyl S-4-methoxy-4-oxo-1-phthalimidomethylbutyl dithiocarbonate
• 英文别名: Methyl 5-(1,3-dioxoisoindol-2-yl)-4-ethoxycarbothioylsulfanylpentanoate
• CAS: 479421-16-4
• 化学式: C₁₇H₁₉NO₅S₂
• 分子量: 381.474
• InChiKey: OSIGTKGDKFDGAC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  25
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  130
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  O-ethyl S-4-methoxy-4-oxo-1-phthalimidomethylbutyl dithiocarbonate 在 盐酸 、 N-氯代丁二酰亚胺 作用下， 以 水 、 乙腈 为溶剂， 反应 0.25h， 以83%的产率得到5-methoxy-5-oxo-1-phthalimidopentane-2-sulfonyl chloride
  参考文献：
  名称：

  Efficient synthesis of protected sulfonopeptides from N-protected 2-aminoalkyl xanthates and thioacetates

  摘要：

  An efficient and convenient method was developed for the synthesis of protected sulfonopeptides via N-chlorosuccimide (NCS)/HCI oxidative chlorination of N-protected 2-aminoallcyl xanthates or thioacetates to the corresponding sulfonyl chlorides followed by aminolysis with amino esters. In the current method, sulfonopeptides containing 1- and 2-substituted taurines were prepared in satisfactory to good yields. It is a useful and efficient strategy for the synthesis of protected sulfonopeptides with functionalized side-chains. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.08.028
• 作为产物：
  描述：

  苯酐 在 过氧化双月桂酰 、 溶剂黄146 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 9.0h， 生成 O-ethyl S-4-methoxy-4-oxo-1-phthalimidomethylbutyl dithiocarbonate
  参考文献：
  名称：

  快速合成具有各种功能化侧链的1-取代牛磺酸

  摘要：

  自由基加成反应和随后的甲酸氧化被用于由N-烯丙基邻苯二甲酰亚胺和各种黄原酸酯合成具有各种官能化侧链的1-取代的牛磺酸。当前的方法显示出高收率和短的合成路线和反应时间。而且，当前的方法是用于合成具有不同官能化侧链的1-取代的牛磺酸的方便且实用的方法。

  DOI：

  10.1016/j.tet.2012.10.029

文献信息

• Task specific onium salts (TSOSs) as efficient soluble supports for Zard radical addition to olefins
  作者：Julien Verron、Jean-Michel Joerger、Mathieu Pucheault、Michel Vaultier

  DOI：10.1016/j.tetlet.2007.04.024

  日期：2007.6

  Task specific onium salts (TSOSs), that is, functionalised ammonium salts, have been used as soluble supports to carry out intermolecular radical additions of xanthates to olefins and functional group interconversions. This methodology provides results by far superior to those reported with other soluble supports and allows for very easy purifications of reaction products.

  任务特定的鎓盐（TSOS），即官能化的铵盐，已用作可溶性载体，以将黄原酸酯分子间自由基加成至烯烃和官能团相互转化。这种方法所提供的结果远远优于其他可溶支持物所报道的结果，并且可以非常轻松地纯化反应产物。
• Radical, One-Step Approach to <i>o</i>-Chlorophenyl Thioethers from Xanthates. A Rapid Access to Vinylsilanes
  作者：Matthieu Corbet、Zorana Ferjančić、Béatrice Quiclet-Sire、Samir Z. Zard

  DOI：10.1021/ol801348u

  日期：2008.8.21

  Xanthates have been readily converted into o-chlorophenyl thioethers using a one-step procedure conducted under radical conditions. In some selected cases, these aryl thioethers were successfully oxidized to the corresponding sulfoxides and sulfenic acid elimination afforded the corresponding vinylsilanes.
• Xanthates and solid-phase chemistry. A new soluble polymer analogue of Wang resin
  作者：Anne-Claude Dublanchet、Marie Lusinchi、Samir Z Zard

  DOI：10.1016/s0040-4020(02)00526-4

  日期：2002.7

  The straightforward synthesis of a new soluble polymer containing a Wang type linker is described. Inter-molecular radical additions of xanthates onto olefins were performed with this new resin in comparison with a classical Wang resin. The new soluble polymer analogue of Wang resin allows easy H-1 monitoring of the reactions and gives better results for the radical transfer while preserving the efficient cleavage conditions of the Wang linker. (C) 2002 Published by Elsevier Science Ltd.