isopropylsulfinyl chloride | 34256-07-0

• 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: isopropylsulfinyl chloride
• 英文别名: Propane-2-sulfinyl Chloride
• CAS: 34256-07-0
• 化学式: C₃H₇ClOS
• mdl: MFCD28118358
• 分子量: 126.607
• InChiKey: OQATUBOUVJHZOK-UHFFFAOYSA-N

物化性质

• 沸点：
  49 °C(Press: 12 Torr)
• 密度：
  1.274±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  6
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  isopropylsulfinyl chloride 在 ammonium hydroxide 作用下， 以 二氯甲烷 、 水 为溶剂， 以9.78 g的产率得到propane-2-sulfinamide
  参考文献：
  名称：

  Rh-Catalyzed Addition of Arylboroxines to Cyclic N-(Isopropanesulfinyl)ketimines

  摘要：

  Arylboroxines, which are easily accessed by drying commercially available arylboronic acids, are added to N-(isopropanesulfinyl)ketimines derived from cyclohexanone, N-Boc-piperidin-4-one, and tetrahydropyran-4-one in high yields and with excellent functional group compatibility via rhodium catalysis. These results contrast with additions to the corresponding ketimines incorporating the larger N-tert-butanesulfinyl group, which give considerably lower yields. Efficient two-step preparation of racemic isopropanesulfinamide from inexpensive isopropyl disulfide and recycling of the isopropanesulfinyl group from the addition products are also described.

  DOI：

  10.1021/jo301634y
• 作为产物：
  描述：

  异丙基二硫醚 在 磺酰氯 、 溶剂黄146 作用下， 反应 5.0h， 以98%的产率得到isopropylsulfinyl chloride
  参考文献：
  名称：

  在位阻胺的立体选择性合成中，N-异丙基亚磺酰亚胺碱与N-叔丁基亚磺酰亚胺碱：对映纯（R）-和（S）-金刚烷胺及三氟甲基化类似物的合成方法得到改进。

  摘要：

  以N-异丙基亚磺酰亚胺为原料，已开发出金刚烷胺及其三氟甲基化类似物的对映体的改进的全立体选择性合成方法，证明在受阻情况下，异丙基作为手性诱导剂优于叔丁基。N-亚磺酰亚胺。

  DOI：

  10.1039/c9ob02241d
• 作为试剂：
  描述：

  tert-butylsulfenic tert-butylsulfinic dithioanhydride 在 isopropylsulfinyl chloride 作用下， 以 氯仿 为溶剂， 反应 12.0h， 生成 叔丁基亚磺酰氯 、 tert-Butylsulfenyl isopropylsulfinyl thioanhydride
  参考文献：
  名称：

  The Chemistry of Alkylsulfenyl Alkylsulfinyl Thioanhydrides. The Mechanism of Decomposition

  摘要：

  The decomposition mechanism of alkylsulfenyl alkylsulfinyl thioanhydrides has been investigated. Although the product mixture is complex in most cases, a detailed decomposition study as well as a careful analysis of the products allows for a proposal for a general mechanism which is interesting and not simple. We find, however, that the decomposition process is consistent with that of related systems.

  DOI：

  10.1021/jo00119a025

文献信息

• Flash vacuum pyrolysis of stabilised phosphorus ylides. Part 13.1 Extrusion of Ph3P from sulfinyl ylides and reactivity of the resulting sulfinyl carbenes
  作者：R. Alan Aitken、Martin J. Drysdale、Bruce M. Ryan

  DOI：10.1039/a806182c

  日期：——

  Six α-sulfinyl phosphorus ylides 6 have been prepared and are found upon flash vacuum pyrolysis at 500 °C to undergo mainly extrusion of Ph3P to give thioesters, presumably by 1,2-oxygen transfer in the initially formed sulfinyl carbenes; for α-arylsulfinyl ylides loss of Ph3PO to give additional products is also observed.

  已经制备了六个α-亚硫酰基磷酰化物6，发现它们在500°C的快速真空热解中主要经历Ph 3 P的挤出，从而生成硫酯，大概是通过在最初形成的亚硫酰基羧甲基中进行的1,2-氧转移来实现的。对于α-芳基亚磺酰基基团，还观察到了Ph 3 PO的损失，从而得到了另外的产物。
• 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。
• A simple and efficient preparation of sulfinyl chlorides from disulfides and sulfuryl chloride
  作者：Joo-Hack Youn、Rudolf Herrmann

  DOI：10.1016/s0040-4039(00)84293-8

  日期：1986.1

  Disulfides react with sulfuryl chloride in the presence of acetic acid to form. the corresponding sulfinyl chlorides in nearly quantitative yield.

  在乙酸的存在下，二硫化物与硫酰氯反应生成。相应的亚硫酰氯的收率接近定量。
• Palladium Nanoparticle Loaded Bifunctional Silica Hybrid Material: Preparation and Applications as Catalyst in Hydrogenation Reactions
  作者：Sabrina K. Surmiak、Carsten Doerenkamp、Philipp Selter、Martin Peterlechner、Andreas H. Schäfer、Hellmut Eckert、Armido Studer

  DOI：10.1002/chem.201604508

  日期：2017.5.2

  Bifunctional mesoporous silica was prepared by co‐condensation of tetraethyl orthosilicate (TEOS) with functionalized organosilanes containing azides or alkoxyamines. Orthogonal functional groups at the particles were selectively addressed in subsequent chemical modifications through “click”‐chemistry (“click to ligand” strategy) and radical nitroxide exchange. Palladation with PdCl2 delivered Pd nanoparticle‐loaded

  双功能介孔二氧化硅是通过将原硅酸四乙酯（TEOS）与含有叠氮化物或烷氧基胺的功能化有机硅烷进行缩聚反应制得的。在随后的化学修饰中，通过“点击”-化学反应（“点击键合配体”策略）和自由基一氧化氮交换，选择性地处理了颗粒上的正交官能团。Palladation用的PdCl 2输送Pd纳米颗粒的加载的二氧化硅材料轴承亚砜和附加氨基酰胺作为在原位还原的Pd借助于稳定配体II-盐。这些功能性颗粒已成功应用于炔烃和烯烃的氢化。这些杂化催化剂在温和条件下实现了醛加氢脱氧和苄基醚裂解。通过IR，TEM / STEM，EDX和固态NMR光谱分析了颗粒。
• A New, Practical One-Pot Synthesis of Unprotected Sulfonimidamides by Transfer of Electrophilic NH to Sulfinamides
  作者：Flavia Izzo、Martina Schäfer、Robert Stockman、Ulrich Lücking

  DOI：10.1002/chem.201703272

  日期：2017.10.26

  An NH transaction: The first direct synthesis of tertiary NH sulfonimidamides from tertiary sulfinamides by electrophilic NH transfer has been achieved. In vitro studies did not reveal any intrinsic flaw of the sulfonimidamide group regarding properties relevant to medicinal chemistry.

  NH交易：已经实现了通过亲电NH转移从叔亚磺酰胺直接合成叔NH磺酰亚胺酰胺的方法。体外研究并未发现磺胺类药物组在与药物化学有关的性质方面有任何内在缺陷。