3-methyloxolane-2-thione | 86633-04-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧唑烯
• 英文名称: 3-methyloxolane-2-thione
• 英文别名: 2(3H)-Furanthione, dihydro-3-methyl-
• CAS: 86633-04-7
• 化学式: C₅H₈OS
• 分子量: 116.184
• InChiKey: SLKFSYLHEDIGDD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  7
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  41.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-methyloxolane-2-thione 、 碘甲烷 在 1-溴基-1-丙烯 、 叔丁基锂 作用下， 生成 2,3-dihydro-4-methyl-5-methylthiofuran
  参考文献：
  名称：

  Acid-catalyzed rearrangement of cyclic allylic monothioketals to exocyclic enol ethers

  摘要：

  DOI：

  10.1021/jo00054a041
• 作为产物：
  描述：

  α-甲基-γ-丁内酯 在 tetraphosphorus decasulfide 作用下， 以 乙腈 为溶剂， 反应 1.5h， 以85%的产率得到3-methyloxolane-2-thione
  参考文献：
  名称：

  Evaluation of thionolactones as a new type of hydrogen sulfide (H2S) donors for a blood pressure regulation

  摘要：

  DOI：

  10.1016/j.bioorg.2021.104650

文献信息

• Construction of Vicinal Quaternary Stereogenic Centers by Enantioselective Direct Mannich-Type Reaction Using a Chiral Bis(guanidino)iminophosphorane Catalyst
  作者：Tadahiro Takeda、Azusa Kondoh、Masahiro Terada

  DOI：10.1002/anie.201601352

  日期：2016.4.4

  the chiral organosuperbase catalyst, the reaction afforded densely functionalized amino‐acid derivatives having vicinal quaternary stereogenic centers, one of which is an all‐carbon quaternary stereogenic center, in good yield with high diastereo‐ and enantioselectivities.

  开发了一种新型的α-亚氨基苯基乙酸酯与硫代内酯的不对称直接曼尼希式反应，该反应在酸性较低的亲核试剂中在α-位带有取代基。使用双（胍基）亚氨基正膦作为手性有机超碱催化剂，该反应提供了具有邻位四元立体异构中心的致密官能化氨基酸衍生物，其中之一是全碳四元立体异构中心，收率高，具有高非对映异构和对映选择性。
• Tributylstannane-mediated cyclization of thionocarboxylic acid derivatives
  作者：Mario D. Bachi、Eric Bosch、Daniella Denenmark、Diana Girsh

  DOI：10.1021/jo00051a024

  日期：1992.12

  Cyclization reactions of various thionoesters and thioamides involving the addition of tri-n-butylstannyl radical to a thiocarbonyl group and intramolecular addition of the resulting radical to a carbon-carbon multiple bond was studied. Dithiocarbonate and (imidazolyl)thiocarbonyl derivatives of homoallylic alcohols gave alpha-substituted gamma-thionobutyrolactones. The reaction is highly dependent on the substitution pattern on the double bond, a high yield of cyclic products being obtained only when the double bond is activated and unhindered. (Z)-4-Phenylbut-3-enyl thionobenzoate afforded 4,5-dihydro-2-phenyl-3-benzylfuran in low yield. In reactions involving a thioamide group, good yields of cyclic products were obtained only from compounds in which the electron density on the nitrogen atom is decreased by an electron attracting group. Cyclization of 1-((E)-4-phenylbut-3-en-1-yl)-5-thioxopyrrolidin-2-one (23) afforded 1-aza-4-benzylbicyclo[3.3.0]oct-4-en-8-one (33).
• Thionation of esters and lactones with the reagent combination of phosphorus pentasulfide and hexamethyldisiloxane
  作者：Thomas J Curphey

  DOI：10.1016/s0040-4039(01)02144-x

  日期：2002.1

  The combination of P4S10 and hexamethyldisiloxane converts esters and lactones to thionoesters and thionolactones in yields comparable to or superior to those obtained with Lawesson's reagent. The method has the advantage that reagent-derived byproducts may be removed by a simple hydrolytic workup or by filtration through silica gel, rather than by chromatography, as required for Lawesson's reagent. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Reaction of thioesters and thiolactones with cyclopentadienylmetal dicarbonyl dimers
  作者：Howard Alper、Frederick W. B. Einstein、Ryuta Nagai、Jean Francois Petrignani、Anthony C. Willis

  DOI：10.1021/om50004a004

  日期：1983.10
• Bachi Mario D., Bosch Eric, Denenmark Daniella, Girsh Diana, J. Org. Chem., 57 (1992) N 25, S 6803-6810
  作者：Bachi Mario D., Bosch Eric, Denenmark Daniella, Girsh Diana

  DOI：——

  日期：——