menthyl p-toluenesulfinate | 98147-48-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: menthyl p-toluenesulfinate
• 英文别名: (5-methyl-2-propan-2-ylcyclohexyl) 4-methylbenzenesulfinate
• CAS: 98147-48-9
• 化学式: C₁₇H₂₆O₂S
• 分子量: 294.458
• InChiKey: NQICGNSARVCSGJ-UHFFFAOYSA-N

物化性质

• 熔点：
  106-107 °C
• 沸点：
  402.3±38.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  45.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  menthyl p-toluenesulfinate 在 三氟甲磺酸三甲基硅酯 、 甲基溴化镁 、 N,N,N,N-tetraethylammonium tetrafluoroborate 、 potassium hydrogencarbonate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 1-(p-tolylsulfinyl)-propan-2-one
  参考文献：
  名称：

  Anodic oxidation of chiral sulfinylamines: a new route to highly diastereoselective α-alkylation of piperidine

  摘要：

  The anodic oxidation of some chiral non-racemic N-arylsulfinyl piperidines was investigated and for the first time alpha methoxylated sulfinyl piperidines were obtained. The so-formed compounds are equivalent of chiral N-sulfinyliminiums and used as new intermediates for the preparation of chiral alpha-substituted piperidine derivatives in good yield and diastereoselectivity. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.05.123
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 丙酮 作用下， 生成 menthyl p-toluenesulfinate
  参考文献：
  名称：

  Phillips, Journal of the Chemical Society, 1925, vol. 127, p. 2586

  摘要：

  DOI：

文献信息

• (<i>Z</i>)-3-<i>p</i>-Tolylsulfinylacrylonitriles as Chiral Dipolarophiles:  Reactions with Diazoalkanes
  作者：José L. García Ruano、Sergio A. Alonso de Diego、Daniel Blanco、Ana M. Martín Castro、M. Rosario Martín、Jesús H. Rodríguez Ramos

  DOI：10.1021/ol016481o

  日期：2001.10.1

  [reaction: see text] The dipolarophilic reactivity of enantiopure (Z)-3-p-tolylsulfinylacrylonitriles (1) has been evaluated with diazoalkanes. 3-Cyanopyrazoles are obtained when R = H, but with R = alkyl (Bn, n-Bu, and t-Bu) only one cycloadduct (4 or 5) is formed in high yield under mild conditions, therefore evidencing a complete control of the regioselectivity and the endo/exo and pi-facial selectivities

  [反应：见正文]已用重氮烷评估了对映纯（Z）-3-对甲苯基亚磺酰基丙烯腈（1）的偶极亲和性。当R = H时获得3-氰基吡唑，但当R =烷基（Bn，n-Bu和t-Bu）时，在温和条件下仅以高收率形成一个环加合物（4或5），因此证明了对苯并吡咯的完全控制。区域选择性以及内/外和面部选择性。这些反应是吡唑啉及其相关结构合成的新的直接途径，并揭示了（Z）-亚磺酰基丙烯腈的优异的双亲性特征。
• Palladium-Catalyzed Intramolecular Direct Arylation of 2-Bromo-diaryl Sulfoxides via C–H Bond Activation
  作者：Thomas Wesch、Anaïs Berthelot-Bréhier、Frédéric R. Leroux、Françoise Colobert

  DOI：10.1021/ol400966q

  日期：2013.5.17

  Efficient access to dibenzothiophene-S-oxides from differently substituted 2-bromo-diarylsulfinyl moieties using ligandless Pd(OAc)2 as the catalyst and KOAc as the base in dimethylacetamide at 130 °C is reported. Various dibenzothiophene-S-oxides were obtained in excellent yields.

  据报道，在130°C下，使用无配体的Pd（OAc）2作为催化剂，以KOAc为碱，有效地从不同取代的2-溴-二芳基亚磺酰基基团中获得了二苯并噻吩-S-氧化物。以优异的产率获得了各种二苯并噻吩-S-氧化物。
• The “thio-Arbuzov” reaction of sulfenate esters with sulfenyl chlorides: Fate of the thiosulfinate product
  作者：Charles Brown、Graham R. Evans

  DOI：10.1016/s0040-4039(96)02096-5

  日期：1996.12

  The further reaction of thiosulfinate esters (putative products of the “Thio-Arbuzov” reaction of sulfenate esters with sulfenyl chlorides) with sulfenyl chlorides and sulfenate esters has been studied. In the former case, sulfinyl chlorides and disulfides are formed. In the latter case sulfinate esters and disulfides are obtained.

  已经研究了硫代亚磺酸酯（亚磺酸酯与亚磺酰氯的“ Thio-Arbuzov”反应的产物）与亚磺酰氯和亚磺酸酯的进一步反应。在前一种情况下，会形成亚磺酰氯和二硫化物。在后一种情况下，获得亚磺酸酯和二硫化物。
• Non-expensive, open-flask and selective catalytic systems for the synthesis of sulfinate esters and thiosulfonates
  作者：Arisson Tranquilino、Silvia R.C.P. Andrade、Ana Paula M. da Silva、Paulo H. Menezes、Roberta A. Oliveira

  DOI：10.1016/j.tetlet.2017.02.025

  日期：2017.3

  Two simple and efficient methods for the synthesis of sulfinate esters and thiosulfonates from sodium salts of sulfinic acids are described. Different alcohols were converted into the corresponding sulfinate esters in good yields and purity in an open flask. By the adjustment of the reaction conditions thiosulfonates could also be obtained in a very short reaction time.

  描述了从亚磺酸钠盐合成亚磺酸酯和硫代磺酸酯的两种简单有效的方法。在敞口烧瓶中将不同的醇以良好的产率和纯度转化为相应的亚磺酸酯。通过调节反应条件，还可以在很短的反应时间内得到硫代磺酸盐。
• Improvement of the diastereoselectivity of the cobalt-mediated [2+2+2] cycloaddition of substituted linear enediynes
  作者：Franck Slowinski、Corinne Aubert、Max Malacria

  DOI：10.1016/s0040-4039(98)02483-6

  日期：1999.1

  The level of the diastereoselectivity of the cobalt-mediated [2+2+2] cyclization of linear enediynes was improved compared to that reported in the literature by substituting the triple or the double bond with ester, phosphine oxide or sulfoxide groups.

  通过用酯，氧化膦或亚砜基团取代三键或双键，与文献报道的相比，钴介导的线性二烯炔的[2 + 2 + 2]环化的非对映选择性水平得到提高。