O-4-Phenylbut-3-yn-1-yl S-methyl dithiocarbonate | 105688-46-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: O-4-Phenylbut-3-yn-1-yl S-methyl dithiocarbonate
• 英文别名: S-methyl O-(4-phenyl-3-butynyl) dithiocarbonate；O-(4-phenylbut-3-ynyl) methylsulfanylmethanethioate
• CAS: 105688-46-8
• 化学式: C₁₂H₁₂OS₂
• 分子量: 236.359
• InChiKey: UWCYTAFMVLAJAM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  66.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  O-4-Phenylbut-3-yn-1-yl S-methyl dithiocarbonate 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 苯 为溶剂， 以49%的产率得到3-Benzyl-4,5-dihydrofuran-2(3H)-thione
  参考文献：
  名称：

  通过将烷氧基羰基自由基分子内加成到乙炔中来合成α-亚烷基-γ-内酯

  摘要：

  α-亚炔基-γ-内酯是通过用三正丁基锡烷处理均丙醇的氯甲酸酯和硒代碳酸酯衍生物而获得的。

  DOI：

  10.1016/s0040-4039(00)84062-9
• 作为产物：
  描述：

  lithium phenylacetylide 在 三氟化硼乙醚 作用下， 生成 O-4-Phenylbut-3-yn-1-yl S-methyl dithiocarbonate
  参考文献：
  名称：

  通过将烷氧基羰基自由基分子内加成到乙炔中来合成α-亚烷基-γ-内酯

  摘要：

  α-亚炔基-γ-内酯是通过用三正丁基锡烷处理均丙醇的氯甲酸酯和硒代碳酸酯衍生物而获得的。

  DOI：

  10.1016/s0040-4039(00)84062-9

文献信息

• Facile Reduction of Dithiocarbonates Derived from Secondary Alcohols with<i>n</i>-Bu₃SnH–Et₃B and Synthesis of 2-Furanthiones and 2-Furanones by Intramolecular Addition of Alkoxythiocarbonyl Free Radicals to Acetylenic Linkages
  作者：Kyoko Nozaki、Koichiro Oshima、Kiitiro Utimoto

  DOI：10.1246/bcsj.63.2578

  日期：1990.9

  reduction of dithiocarbonates or thiocarbonates by n-Bu3SnH–Et3B easily gives the corresponding hydrocarbons. The intermediate alkoxythiocarbonyl radical equivalents are trapped by properly located carbon–carbon multiple bonds. The dithiocarbonates derived from either homopropargylic or homoallylic alcohols produce tetrahydrofuranones upon treatment with n-Bu3SnH–Et3B. Application of this new method

  n-Bu3SnH–Et3B 还原二硫代碳酸盐或硫代碳酸盐很容易得到相应的碳氢化合物。中间体烷氧基硫代羰基自由基等价物被适当定位的碳-碳多重键捕获。衍生自高炔丙醇或高烯丙醇的二硫代碳酸酯在用 n-Bu3SnH–Et3B 处理后产生四氢呋喃酮。还描述了这种新方法在将羰基化合物转化为烯烃中的应用。
• 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).
• Synthesis of lactones by intramolecular addition of alkoxythiocarbonyl free radicals to acetylenes
  作者：Kyoko Nozaki、Koichiro Oshima、Kiitiro Utimoto

  DOI：10.1016/s0040-4039(00)82284-4

  日期：——
• NOZAKI, KYOKO;OSHIMA, KOICHIRO;UTIMOTO, KIITIRO, BULL. CHEM. SOC. JAP., 63,(1990) N, C. 2578-2583
  作者：NOZAKI, KYOKO、OSHIMA, KOICHIRO、UTIMOTO, KIITIRO

  DOI：——

  日期：——
• 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：——