丁-1-烯-4-硫醇 | 5954-70-1

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醇
• 中文名称: 丁-1-烯-4-硫醇
• 英文名称: 3-buten-1-thiol
• 英文别名: but-3-ene-1-thiol；4-Mercapto-buten-(1)；3-Butene-1-thiol
• CAS: 5954-70-1
• 化学式: C₄H₈S
• 分子量: 88.1735
• InChiKey: MMALMXBEMBYJSC-UHFFFAOYSA-N

物化性质

• 沸点：
  250 °C
• 密度：
  0.9198 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  5
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  1
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 海关编码：
  2930909090

反应信息

• 作为反应物：
  描述：

  丁-1-烯-4-硫醇 在 potassium permanganate 、 copper(II) sulfate 作用下， 以 二氯甲烷 为溶剂， 以75%的产率得到di(but-3-enyl) disulfide
  参考文献：
  名称：

  Alkenylthioimidoyl Radicals:  Competition between β-Scission and Cyclization to Dihydrothiophen-2-ylidene-amines

  摘要：

  But-3-enylthiolmidoyl radicals were shown by EPR spectroscopy and end product analysis to ring-close predominantly in the 5-exo mode with a rate constant of 2.4 x 10(4) s(-1) at 300 K to afford substituted dihydrothiophenylmethyl radicals. This ring closure was in competition with dissociation to but-3-enyl radicals and an isothiocyanate. The dissociation predominated at temperatures above ca. 300 K.

  DOI：

  10.1021/ol034073+
• 作为产物：
  描述：

  thioacetic acid S-but-3-enyl ester 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 生成 丁-1-烯-4-硫醇
  参考文献：
  名称：

  铬/光氧化还原双催化合成 α-苄醇、异苯并二氢吡喃酮、1,2-羟基醇和 1,2-硫醇

  摘要：

  通过采用结合铬化学和光氧化还原催化的双重催化方法，成功合成了α-苄醇、官能化异色满酮、1,2-羟基醇和 1,2-硫醇。这提出了一种在温和条件下具有高官能团耐受性的方法。

  DOI：

  10.1002/anie.202212136

文献信息

• Ni-Catalyzed Cross-Electrophile Coupling of Aryl Triflates with Thiocarbonates via C–O/C–O Bond Cleavage
  作者：Zhaodong Zhu、Yuxin Gong、Weiqi Tong、Weichao Xue、Hegui Gong

  DOI：10.1021/acs.orglett.1c00313

  日期：2021.3.19

  A nickel-catalyzed reductive coupling of aryl triflates with thiocarbonates is reported here. Both electron-rich and -deficient aryl C(sp2)–O electrophiles as well as a class of O-tBu S-alkyl thiocarbonates are compatible with the optimized reaction conditions, as evidenced by 49 examples. The reaction also proceeds with good chemoselective cleavage of the C–O bond with regard to thioesters. This work

  此处报道了芳基三氟甲磺酸酯与硫代碳酸酯的镍催化还原偶联。富电子和不足的芳基C（sp 2）-O亲电体以及一类O - t Bu S-烷基硫代碳酸酯都与优化的反应条件兼容，如49个实例所示。对于硫代酯，该反应还会以良好的C–O键化学选择性裂解来进行。这项工作拓宽了镍催化的还原交叉亲电子偶联反应的范围。
• Enantioselective Total Synthesis of (+)-Largazole, a Potent Inhibitor of Histone Deacetylase
  作者：Arun K. Ghosh、Sarang Kulkarni

  DOI：10.1021/ol8014623

  日期：2008.9.1

  An enantioselective total synthesis of the cytotoxic natural product (+)-largazole (1) is described. It is a potent histone deacetylase inhibitor. Our synthesis is convergent and involves the assembly of thiazole 3-derived carboxylic acid with amino ester 4 followed by cycloamidation of the corresponding amino acid. The synthesis features an efficient cross-metathesis, an enzymatic kinetic resolution

  描述了细胞毒性天然产物 (+)-拉格唑 (1) 的对映选择性全合成。它是一种有效的组蛋白脱乙酰酶抑制剂。我们的合成是收敛的，涉及噻唑 3 衍生的羧酸与氨基酯 4 的组装，然后是相应氨基酸的环酰胺化。该合成具有高效的交叉复分解、β-羟基酯的酶动力学拆分、选择性去除 Boc 保护基团、HATU/HOAt 促进的环酰胺化反应以及对敏感硫酯官能团的合成操作。
• Triton B Mediated One-Pot Synthesis of Thiocarbonic Ester Derivatives in Non-Aqueous Medium
  作者：Neha Singh、Richa Khare、Krishna Srivastava

  DOI：10.14233/ajchem.2019.22025

  日期：2019.8.10

  A differentiated series of thiocarbonic acid esters have been synthesized and characterized in good to excellent yields with the help of thiols, carbon di sulphide and alkyl/aryl halides in DMSO with benzyl trimethylammonium hydroxide where Triton B acts as a catalyst. This method is safer and efficient as compared to other conventional methods.

  在 DMSO 中的硫醇、二硫化碳和烷基/芳基卤化物与氢氧化苄基三甲基铵（Triton B 充当催化剂）的帮助下，合成了一系列不同的硫代碳酸酯，并以良好至优异的产率进行了表征。与其他传统方法相比，该方法更安全、更有效。
• Radical Cyclizations of Alkenyl Acylphosphonate Derivatives under Thermal and Photochemical Conditions
  作者：Chang Ho Cho、Sunggak Kim、Motoki Yamane、Hironori Miyauchi、Koichi Narasaka

  DOI：10.1246/bcsj.78.1665

  日期：2005.9

  The use of alkenyl acylphosphonate and acylphosphine oxide derivatives as acceptors in radical cyclizations was studied under thermal and photochemical conditions, respectively. The cyclizations of alkenyl acylphosphonates under thermal conditions occurred smoothly in refluxing dioxane using benzoyl peroxide as an initiator; the addition of diethyl phosphite increased the chemical yield. Photochemically induced cyclizations of alkenyl acyldiphenylphosphine oxides at 300 nm gave similar results, although a notable difference was observed in one case. The intramolecular cyclization of S-but-3-enyl phosphinothiolformates occurred under thermal and photochemical conditions, providing thiolactones, whereas S-pent-4-enyl phosphinothiolformate afforded the tetrahydrothiophene derivative under similar conditions.

  在热和光化学条件下，分别研究了烯丙基酰基膦酸酯和酰基膋氧化物衍生物作为受体在自由基环合反应中的应用。热条件下烯丙基酰基膦酸酯的环合反应在回流的二恶烷中顺利进行，以苯甲酰过氧化物为引发剂；加入亚磷酸二乙酯可提高化学产率。在300 nm光化学诱导下，烯丙基酰基二苯基膦氧化物的环合反应得到类似结果，尽管在一个案例中观察到了显著差异。在热和光化学条件下，S-丁-3-烯基膦硫酯的内环化反应提供了硫酯，而S-戊-4-烯基膦硫酯在类似条件下生成了四氢噻吩衍生物。
• On the Preparation and Determination of Configurational Stability of Chiral Thio- and Bromo[D₁]methyllithiums
  作者：Anna Wieczorek、Friedrich Hammerschmidt

  DOI：10.1021/jo301441g

  日期：2012.11.16

  Thio- and bromo[D1]methyllithiums (ee 99%) were generated from the respective stannanes by tin–lithium exchange at temperatures ranging from 0 to −95 °C. Thio[D1]methyllithiums 6 were found to be microscopically configurationally labile on the time scale of the thiophosphate-α-mercaptophosphonate rearrangement even at −95 °C. Thio[D1]methyllithiums 13a and 13b underwent a thia-[2,3]-Wittig rearrangement

  硫代和溴代 [D 1 ] 甲基锂（ee 99%）是通过锡-锂交换在 0 到 -95 °C 的温度下从各自的锡烷中生成的。发现硫代[D 1 ] 甲基锂6在硫代磷酸盐-α-巯基膦酸盐重排的时间尺度上即使在-95°C 下在微观上也不稳定。Thio[D 1 ] 甲基锂13a和13b经历了低至 -95 °C 的 thia-[2,3]-Wittig 重排，而13b仅低至 -50 °C。前者在-95°C以下微观构型稳定，后者在-50°C下完全消旋。手性溴[D 1] 甲基锂在 -78 °C 时化学性质不稳定，但在其加入苯甲醛和苯乙酮的时间尺度上在微观结构上是稳定的。