ethoxycarbonylmethanesulphenyl chloride | 71032-81-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethoxycarbonylmethanesulphenyl chloride
• 英文别名: Ethyl 2-chlorosulfanylacetate
• CAS: 71032-81-0
• 化学式: C₄H₇ClO₂S
• 分子量: 154.617
• InChiKey: CBFIULYTFGVESV-UHFFFAOYSA-N

物化性质

• 沸点：
  40-42 °C(Press: 1 Torr)
• 密度：
  1.253±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  51.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethoxycarbonylmethanesulphenyl chloride 在 三乙胺 作用下， 生成 ethyl thioxoacetate
  参考文献：
  名称：

  呋喃通过苯甲酰硫化物的功能化

  摘要：

  描述了一种温和，有效的光化学方法，用于通过苯甲酰硫化物使呋喃官能化。

  DOI：

  10.1016/s0040-4039(00)61862-2
• 作为产物：
  描述：

  diethyl 2,2'-disulfanediyldiacetate 在 磺酰氯 作用下， 以 四氯化碳 为溶剂， 生成 ethoxycarbonylmethanesulphenyl chloride
  参考文献：
  名称：

  通过碱催化烷基邻苯二甲酰亚胺基硫烷基乙酸酯的裂解形成的亲二烯丙基硫代醛和二硫代酸酯

  摘要：

  在室温下用三乙胺处理乙基和亚甲基邻苯二甲硫基乙酸乙酸乙酯1a和1b产生[eqn。（1）]瞬态硫醛，乙基和甲基硫代乙酸甲酯2，已用2,3-二甲基-1,3-二烯就地捕获，从而以高收率生产了Diels-Alder环加合物8a和8b。类似地，分别获得了硫代氧乙酸乙酯2a和蒽，环己-1，3-二烯和环戊二烯的环加合物9、10和11a和12a。以endo ：exo = 7：3的比例形成的环戊二烯的endo -11a和exo -12a环加合物，在甲苯中加热回流时可逆分解，得到相同的平衡混合物，endo：exo＝ 3∶7，因此可以切断作为硫代乙酸乙酯2a的“清洁”辅助前体。因此，当环加合物11a和12a的混合物依次与二甲基丁二烯和（E，E）-1，4-二苯基丁-1，3-二烯，得到相应的二烯环加合物8a和13。出乎意料的是，在二甲基丁二烯存在下，用三乙胺（1摩尔当量）和4-二甲基氨基吡啶（DMAP）（0.1摩尔

  DOI：

  10.1039/p19960000977

文献信息

• Reactions of Wittig Reagents with Episulfides or Elemental Sulfur
  作者：Kentaro Okuma、Yuji Tachibana、Jun-ichi Sakata、Takashi Komiya、Isao Kaneko、Yasuo Komiya、Yusuke Yamasaki、Shin-ichi Yamamoto、Hiroshi Ohta

  DOI：10.1246/bcsj.61.4323

  日期：1988.12

  The reactions of Wittig reagents with episulfides gave symmetrical olefins and triphenylphosphine sulfide in moderate yields. The same olefins were obtained by reactions of Wittig reagents with elemental sulfur. These reactions might proceed through thiocarbonyl intermediates, the existence of which was confirmed by Diels–Alder reactions with dienes.

  Wittig 试剂与环硫化物的反应以中等产率得到对称的烯烃和硫化三苯基膦。通过 Wittig 试剂与元素硫反应获得相同的烯烃。这些反应可能通过硫代羰基中间体进行，硫代羰基中间体的存在已通过与二烯的 Diels-Alder 反应证实。
• 1-dethia-2-thia-cephalosporanic acids
  申请人：Roussel Uclaf

  公开号：US05663164A1

  公开（公告）日：1997-09-02

  Novel 1-dethia-2-thia-cephalosporanic acid derivatives of the formula ##STR1## wherein R is selected from the group consisting of ##STR2## Ra is an organic radical, R.sub.i and R.sub.j are individually selected from the group consisting of hydrogen, aliphatic, aromatic and heterocycle or taken together with the nitrogen atom to which they are attached form an optionally substituted cycle or R.sub.b NH--, R.sub.b is optionally substituted carbocyclic or heterocyclic aryl, R.sub.1 and --COM are as defined in the specification, R.sub.4 is hydrogen or methoxy, n.sub.2 is 0, 1 or 2 and their non-toxic, pharmaceutically acceptable acid addition salts in racemic or optically active form having antibiotic activity and their preparation and novel intermediates.

  1-德西亚-2-硫代头孢菌素酸衍生物的新颖式样的分子式为##STR1## 其中R选自##STR2## Ra是有机基团，R.sub.i和R.sub.j分别选自氢、脂肪、芳香和杂环的群，或者与它们附着的氮原子一起形成一个可选取代的环，或者R.sub.b NH--，R.sub.b是可选取代的碳环或杂环芳基，R.sub.1和--COM如规范所定义，R.sub.4是氢或甲氧基，n.sub.2为0、1或2，它们的无毒、药用可接受的酸盐以拉丁或光学活性形式具有抗生素活性，并且它们的制备和新颖中间体。
• Generation of ethyl thioxoacetate, a dienophilic thioaldehyde
  作者：Christine M. Bladon、Irene E. G. Ferguson、Gordon W. Kirby、Alistair W. Lochead、Duncan C. McDougall

  DOI：10.1039/c39830000423

  日期：——

  Ethoxycarbonylmethanesulphenyl chloride reacts with triethylamine to give the transient thioaldehyde, ethyl thioxoacetate, which has been trapped, in situ, by cycloaddition to various conjugated dienes.

  乙氧羰基甲磺酰氯与三乙胺反应生成瞬态硫醛，硫代氧代乙酸乙酯，已通过环加成将其原位捕获到各种共轭二烯中。
• Synthesis of Aryl Thioethers through the <i>N</i>-Chlorosuccinimide-Promoted Cross-Coupling Reaction of Thiols with Grignard Reagents
  作者：Jun-Hao Cheng、Chintakunta Ramesh、Hsin-Lun Kao、Yu-Jen Wang、Chien-Ching Chan、Chin-Fa Lee

  DOI：10.1021/jo302088t

  日期：2012.11.16

  approach for the synthesis of aryl sulfides through the coupling of thiols with Grignard reagents in the presence of N-chlorosuccinimide is described. The sulfenylchlorides were formed when thiols were treated with N-chlorosuccinimide, and the resulting sulfenylchlorides were then directly reacted with Grignard reagents to provide aryl sulfides in good to excellent yields under mild reaction conditions.

  描述了一种在N-氯代琥珀酰亚胺存在下通过硫醇与格氏试剂的偶联来合成芳基硫化物的方便的一锅法。当用N-氯代琥珀酰亚胺处理硫醇时，形成了亚硫酰氯，然后在温和的反应条件下，将所得的亚硫酰氯与格氏试剂直接反应，以良好的收率获得了芳基硫化物。所用的反应条件容许包括酯，氟和氯的官能团。重要的是要注意，该方法的反应时间短（总计30分钟），是现有方案中芳基硫醚合成的另一种方法。
• ACAT inhibitors derived from hetero-Diels-Alder cycloadducts of thioaldehydes
  作者：Richard G. Wilde、Jeffrey T. Billheimer、Sandie J. Germain、Elizabeth A. Hausner、Paul C. Meunier、Deborah A. Munzer、Janet K. Stoltenborg、Peter J. Gillies、Deborah L. Burcham、Shiew-Mai Huang、John D. Klaczkiewicz、Soo S. Ko、Ruth R. Wexler

  DOI：10.1016/0968-0896(96)00143-5

  日期：1996.9

  Acyl-CoA:cholesterol acyltransferase (ACAT) is the enzyme largely responsible for intracellular cholesterol esterification. A systemic inhibitor of ACAT is believed to be able to slow or even reverse the atherosclerotic process. Towards that goal, a series of cyclic sulfides, derived from the hetero-Diels-Alder reaction of thioaldehydes with 1,3-dienes, and bearing carboxamide substituents, were prepared and evaluated for in vitro (in several tissues and species) and ex vivo ACAT inhibition. Minor changes in subsequent structure were found to have a significant effect in optimization of the biological activity of this series of compounds. Copyright (C) 1996 The DuPont Merck Pharmaceutical Company.