allylsulfinyl chloride | 118678-32-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 亚磺酸及其衍生物
• 英文名称: allylsulfinyl chloride
• 英文别名: prop-2-ene-1-sulfinic chloride；(±)-prop-2-ene-1-sulfinic chloride；prop-2-ene-1-sulfinyl chloride
• CAS: 118678-32-3
• 化学式: C₃H₅ClOS
• 分子量: 124.591
• InChiKey: BUGRIKURMVUKCV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  6
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  36.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  丙烷-1-硫醇 、 allylsulfinyl chloride 在 吡啶 作用下， 以 乙醚 为溶剂， 反应 1.0h， 以89%的产率得到2-propene-1-sulfinothioic acid S-n-propyl ester
  参考文献：
  名称：

  Allium Chemistry:  Supercritical Fluid Extraction and LC−APCI−MS of Thiosulfinates and Related Compounds from Homogenates of Garlic, Onion, and Ramp. Identification in Garlic and Ramp and Synthesis of 1-Propanesulfinothioic Acid S-Allyl Ester

  摘要：

  Supercritical fluid (SF) extracts of homogenized garlic (Allium sativum L.), ramp (A. tricoccum Ait.), chemical ionization mass spectrometric identification. The major thiosulfinates from garlic and ramp were readily characterized by this technique. Small quantities of ajoene, a potent antithrombotic agent, were also found in SP extracts of garlic homogenates. The profiles of onion juice extracts revealed the usual thiosulfinates, zwiebelanes, and bissulfine reported in prior studies, as well as cepaenes previously identified in extracts of onion juice through extensive isolation steps and spectroscopic methods. The presence of trace quantities of allyl compounds in onion juice and propyl compounds in garlic and ramp-homogenates has been verified by LC-mass spectrometry (MS). The presence of these compounds was not readily evident in previous analyses using gas chromatography-MS with cold-on-column injection and reversed-phase or normal phase LC with UV detection.

  DOI：

  10.1021/jf970314e
• 作为产物：
  描述：

  3-氯丙烯 在 氯化亚砜 、 二氧化硫 、 magnesium 作用下， 生成 allylsulfinyl chloride
  参考文献：
  名称：

  Allium Chemistry:  Supercritical Fluid Extraction and LC−APCI−MS of Thiosulfinates and Related Compounds from Homogenates of Garlic, Onion, and Ramp. Identification in Garlic and Ramp and Synthesis of 1-Propanesulfinothioic Acid S-Allyl Ester

  摘要：

  Supercritical fluid (SF) extracts of homogenized garlic (Allium sativum L.), ramp (A. tricoccum Ait.), chemical ionization mass spectrometric identification. The major thiosulfinates from garlic and ramp were readily characterized by this technique. Small quantities of ajoene, a potent antithrombotic agent, were also found in SP extracts of garlic homogenates. The profiles of onion juice extracts revealed the usual thiosulfinates, zwiebelanes, and bissulfine reported in prior studies, as well as cepaenes previously identified in extracts of onion juice through extensive isolation steps and spectroscopic methods. The presence of trace quantities of allyl compounds in onion juice and propyl compounds in garlic and ramp-homogenates has been verified by LC-mass spectrometry (MS). The presence of these compounds was not readily evident in previous analyses using gas chromatography-MS with cold-on-column injection and reversed-phase or normal phase LC with UV detection.

  DOI：

  10.1021/jf970314e

文献信息

• The reaction of 2-trimethylsilylethyl sulfoxides with sulfuryl chloride. A fragmentation route to sulfinyl chlorides.
  作者：Adrina L. Schwan、Robert Dufault

  DOI：10.1016/0040-4039(92)88076-h

  日期：1992.7

  Sulfinyl chlorides were prepared in good to excellent yields by reacting aryl or alkyl 2-trimethylsilylethyl sulfoxides with SO2Cl2.

  通过使芳基或烷基2-三甲基甲硅烷基乙基亚砜与SO 2 Cl 2反应，以高至优异的产率制备亚硫酰氯。
• Sulfonimidates: Useful Synthetic Intermediates for Sulfoximine Synthesis via C–S Bond Formation
  作者：Priscilla Mendonça Matos、William Lewis、Jonathan C. Moore、Robert A. Stockman

  DOI：10.1021/acs.orglett.8b01473

  日期：2018.6.15

  Medicinally relevant sulfoximines are accessed from C–S coupling of sulfonimidates and commercially available organomagnesium reagents. Sulfonimidates are conveniently synthesized by oxidative alkoxylation of readily available sulfinamides. This constitutes a general C–S coupling approach for the synthesis of sulfoximines.

  医药上相关的亚砜肟类可从亚磺酰胺盐与市售有机镁试剂的CS偶联中获得。磺酰亚胺盐可通过容易获得的亚磺酰胺的氧化烷氧基化方便地合成。这构成了合成亚砜肟类的常规C–S偶联方法。
• Oxidative Fragmentations of 2-(Trimethylsilyl)ethyl Sulfoxides − Routes to Alkane-, Arene-, and Highly Substituted 1-Alkenesulfinyl Chlorides
  作者：Adrian L. Schwan、Rick R. Strickler、Robert Dunn-Dufault、Denis Brillon

  DOI：10.1002/1099-0690(200105)2001:9<1643::aid-ejoc1643>3.0.co;2-m

  日期：2001.5

  collection of alkyl, aryl, and 1-alkenyl 2-(trimethylsilyl)ethyl sulfoxides is outlined, using mostly vinyltrimethylsilane or 2-(trimethylsilyl)ethanesulfenyl chloride (5) as key starting materials. The 2-(trimethylsilyl)ethyl group can be cleaved from many of the sulfoxides under oxidative fragmentation conditions using sulfuryl chloride and the reaction represents a new protocol for sulfinyl chloride synthesis

  概述了烷基、芳基和 1-烯基 2-(三甲基甲硅烷基) 乙基亚砜的制备，主要使用乙烯基三甲基硅烷或 2-(三甲基甲硅烷基) 乙磺酰氯 (5) 作为关键起始材料。2-（三甲基甲硅烷基）乙基可以在氧化断裂条件下使用磺酰氯从许多亚砜上裂解下来，该反应代表了亚磺酰氯合成的新方案。该方法适用于大多数烷烃和芳烃亚磺酰氯 (3)，但仅限于高度取代的乙烯基亚磺酰氯。具有减少的双键取代 (6, 7, 11) 的 1-烯基 2-（三甲基甲硅烷基）乙基亚砜会屈服于涉及双键氯化的反应。硅的 β 效应被用来解释 2-（三甲基甲硅烷基）乙基在氧化裂解反应条件下诱导 CS 键断裂的能力。提供了一种机制来解释 2-（三甲基甲硅烷基）乙基的 β-硅原子所起的作用。事实上，硅原子是自我牺牲的，因为它将反应过程从通常的 α-碳氯化模式转移到氧化裂解之一，从而失去 2-（三甲基甲硅烷基）乙基。整个反应需要硅原子通过超共轭提供电子密
• 10.1021/ol403508
  作者：Bai, Jianfei、Zambron, Bartosz K.、Vogel, Pierre

  DOI：10.1021/ol403508

  日期：——
• <i>Allium</i> Chemistry:  Supercritical Fluid Extraction and LC−APCI−MS of Thiosulfinates and Related Compounds from Homogenates of Garlic, Onion, and Ramp. Identification in Garlic and Ramp and Synthesis of 1-Propanesulfinothioic Acid <i>S</i>-Allyl Ester
  作者：Elizabeth M. Calvey、Jean E. Matusik、Kevin D. White、Russell DeOrazio、Deyou Sha、Eric Block

  DOI：10.1021/jf970314e

  日期：1997.11.1

  Supercritical fluid (SF) extracts of homogenized garlic (Allium sativum L.), ramp (A. tricoccum Ait.), chemical ionization mass spectrometric identification. The major thiosulfinates from garlic and ramp were readily characterized by this technique. Small quantities of ajoene, a potent antithrombotic agent, were also found in SP extracts of garlic homogenates. The profiles of onion juice extracts revealed the usual thiosulfinates, zwiebelanes, and bissulfine reported in prior studies, as well as cepaenes previously identified in extracts of onion juice through extensive isolation steps and spectroscopic methods. The presence of trace quantities of allyl compounds in onion juice and propyl compounds in garlic and ramp-homogenates has been verified by LC-mass spectrometry (MS). The presence of these compounds was not readily evident in previous analyses using gas chromatography-MS with cold-on-column injection and reversed-phase or normal phase LC with UV detection.