戊烷-3-硫醇 | 616-31-9

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醇
• 中文名称: 戊烷-3-硫醇
• 英文名称: pentane-3-thiol
• 英文别名: 3-pentanethiol；3-Pentanthiol；Pentanthiol-(3)
• CAS: 616-31-9
• 化学式: C₅H₁₂S
• mdl: MFCD11193802
• 分子量: 104.216
• InChiKey: WICKAMSPKJXSGN-UHFFFAOYSA-N

物化性质

• 熔点：
  -110.8°C
• 沸点：
  113.9°C
• 密度：
  0.837
• LogP：
  2.66
• 物理描述：
  Clear to pale yellow liquid; Fruity roasted savoury aroma
• 溶解度：
  Very Slightly soluble in water
• 折光率：
  1.444 - 1.448
• 保留指数：
  758

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  6
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  戊烷-3-硫醇 在 过氧乙酸 、 溶剂黄146 作用下， 反应 2.0h， 生成 3-戊烷磺酸
  参考文献：
  名称：

  Foldamers as Reactive Sieves:  Reactivity as a Probe of Conformational Flexibility

  摘要：

  A series of m-phenyleneethynylene (mPE) oligomers modified with a dimethylaminopyridine (DMAP) unit were treated with methyl sulfonates of varying sizes and shapes, and the relative reactivities were measured by UV spectrophotometry. Using a small-molecule DMAP analogue as a reference, each of the methyl sulfonates was shown to react at nearly identical rate. In great contrast, oligomers that are long enough to fold, and hence capable of binding the methyl sulfonate, experience rate enhancements of 18-1600-fold relative to that of the small-molecule analogue, depending on the type of alkyl chain attached to the guest. Three different oligomer lengths were studied, with the longest oligomers exhibiting the fastest rate and greatest substrate specificity. Even large, bulky guests show slightly enhanced methylation rates compared to that with the reference DMAP, which suggests a dynamic nature to the oligomer's binding cavity. Several mechanistic models to describe this behavior are discussed.

  DOI：

  10.1021/ja067670a
• 作为产物：
  描述：

  3-戊醇 在 吡啶 、 potassium thioacetate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 戊烷-3-硫醇
  参考文献：
  名称：

  [EN] CHEMICAL COMPOUNDS
  [FR] COMPOSÉS CHIMIQUES

  摘要：

  本公开描述了新颖的化合物，或其药用可接受的盐，含有它们的药物组合物，以及它们的医疗用途。本公开的化合物具有作为Janus激酶（JAK）的双重调节剂的作用，单独使用，或与一个或多个附加机制（包括酪氨酸激酶，如TrkA或Syk，以及PDE4）结合使用，并且在治疗或控制炎症、自身免疫疾病、癌症以及其他调节JAK会可取的失调和其他适应症中是有用的。此外，还描述了通过施用本处所述的化合物来治疗炎症、自身免疫疾病、癌症以及其他易受JAK和PDE4抑制的状况的方法。

  公开号：

  WO2021003501A1

文献信息

• [EN] CHEMICAL COMPOUNDS<br/>[FR] COMPOSÉS CHIMIQUES
  申请人：BORAGEN INC

  公开号：WO2021003501A1

  公开（公告）日：2021-01-07

  The present disclosure describes novel compounds, or their pharmaceutically acceptable salts, pharmaceutical compositions containing them, and their medical uses. Compounds of the disclosure have activity as dual modulators of Janus kinase (JAK), alone, or in combination with one or more of an additional mechanism, including a tyrosine kinase, such as TrkA or Syk, and PDE4, and are useful in the in the treatment or control of inflammation, auto-immune diseases, cancer, and other disorders and indications where modulation of JAK would be desirable. Also described herein are methods of treating inflammation, auto-immune diseases, cancer, and other conditions susceptible to inhibition of JAK and PDE4 by administering a compound herein described.

  本公开描述了新颖的化合物，或其药用可接受的盐，含有它们的药物组合物，以及它们的医疗用途。本公开的化合物具有作为Janus激酶（JAK）的双重调节剂的作用，单独使用，或与一个或多个附加机制（包括酪氨酸激酶，如TrkA或Syk，以及PDE4）结合使用，并且在治疗或控制炎症、自身免疫疾病、癌症以及其他调节JAK会可取的失调和其他适应症中是有用的。此外，还描述了通过施用本处所述的化合物来治疗炎症、自身免疫疾病、癌症以及其他易受JAK和PDE4抑制的状况的方法。
• Palladium-Catalyzed γ-C(sp³ )−H Arylation of Thiols by a Detachable Protecting/Directing Group
  作者：Likun Jin、Jianchun Wang、Guangbin Dong

  DOI：10.1002/anie.201807760

  日期：2018.9.17

  Reported herein is a palladium‐catalyzed, directed γ‐C(sp3)−H arylation of protected thiols. The key is to utilize Michael acceptors as a dual reagent to install a protecting/directing group on thiols by a thiol‐Michael click reaction, and remove it later under basic conditions. The C−H arylation proceeds with high functional‐group tolerance and the deprotected thiols can be further transformed into

  本文报道了受保护的硫醇的钯催化定向γ-C（sp 3）-H芳基化反应。关键是利用迈克尔受体作为双重试剂，通过巯基-迈克尔点击反应在巯基上安装一个保护/导向基团，然后在碱性条件下将其除去。CH芳基化反应具有较高的官能团耐受性，脱保护的硫醇可进一步转化为其他含硫化合物。这种独特的活化方式可以为未活化位置的硫醇或其他含硫化合物的位点选择性官能化打开大门。
• The effect of substitutents at alkylsulfanyl/arylsulfanyl non-peripherally substituted phthalocyanines: Spectral and photophysical properties, basicity and photostability
  作者：Antonin Cidlina、Zuzana Pausimova、Miroslav Miletin、Petr Zimcik、Veronika Novakova

  DOI：10.1142/s1088424615500832

  日期：2015.10

  A series of magnesium, zinc and metal-free derivatives of non-peripherally substituted phthalocyanines (Pcs) bearing alkylsulfanyl or arylsulfanyl groups of different bulkiness was synthesized. Their spectral and photophysical properties including also the basicity of azomethine nitrogens and photostability were compared within the series as well as with similar peripherally substituted Pcs. Non-peripheral position of substituents led to the 70[Formula: see text]nm red-shift of Q-band in comparison to the peripherally substituted Pcs. However, unexpected blue-shift of approximately 50[Formula: see text]nm was observed in the series of non-peripherally substituted Pcs for the most bulky tert-butylsulfanyl derivative caused probably by extreme distortion of the macrocycle. The substitution had no effect on photophysical properties and compounds reached [Formula: see text] values 0.74–0.76 and [Formula: see text] 0.053–0.080 for zinc complexes, and [Formula: see text] 0.47–0.51 and [Formula: see text] 0.10–0.17 for magnesium complexes following the rule of heavy atom effect. Generally, non-peripherally substituted Pcs possessed improved singlet oxygen production in comparison to peripherally substituted ones. The photostability of the target compounds decreased with the red-shift of their absorption maxima with the arylsulfanyl derivatives being less photostable. The basicity of azomethine nitrogens was clearly dependent on the position and the character of substituent. Thus, non-peripherally substituted Pcs showed extraordinary increased basicity over the peripherally substituted ones with the most pronounced effect at alkylsulfanyl derivatives.

  我们合成了一系列带有不同体积的烷基硫酰基或芳基硫酰基的非外周取代酞菁（Pcs）的镁、锌和无金属衍生物。对这些衍生物的光谱和光物理特性进行了比较，包括偶氮甲基硝基的碱性和光稳定性。与外围取代的 Pcs 相比，非外围位置的取代基导致 Q 波段发生了 70[式：见正文]纳米的红移。然而，在非外周取代的 Pcs 系列中，最粗大的叔丁基硫酰基衍生物出现了大约 50[式：见正文]纳米的意想不到的蓝移，这可能是由于大环的极度变形造成的。取代对光物理性质没有影响，锌络合物的[式：见正文]值为 0.74-0.76 和[式：见正文]0.053-0.080，镁络合物的[式：见正文]值为 0.47-0.51 和[式：见正文]0.10-0.17。一般来说，与外围取代的 Pcs 相比，非外围取代的 Pcs 能更好地产生单线态氧。目标化合物的光稳定性随着其吸收最大值的红移而降低，其中芳基硫代衍生物的光稳定性较差。偶氮甲基硝基的碱性明显取决于取代基的位置和性质。因此，非外周取代的 Pcs 比外周取代的 Pcs 具有更强的碱性，其中烷基硫衍生物的效果最为明显。
• Reactions of 2-(α-Haloalkyl)thiiranes with nucleophilic reagents: V. Reactions of 2-(α-Chloroalkyl)thiiranes with organolithium compounds
  作者：A. A. Tomashevskii、V. V. Sokolov、A. A. Potekhin

  DOI：10.1134/s1070428010120080

  日期：2010.12

  corresponding allyl sulfides. The reactions of diastereoisomeric erythro- and threo-2-(1-chloroethyl)thiiranes with phenyllithium were stereospecific, and they afforded (E)- and (Z)-1-phenylsulfanylbut-2-enes, respectively. 3-Chloromethyl-2,2-dimethylthiirane and phenyllithium gave rise to a mixture of 3-methyl-3-phenylsulfanylbut-1-ene and 3-methyl-1-phenylsulfanylbut-2-ene. The reactions of 2-chloromethylthiiranes

  2-（α-卤代烷基）硫烷与甲基，丁基和苯基锂反应，得到相应的烯丙基硫化物。非对映异构的赤-和苏-2-（1-氯乙基）硫烷与苯基锂的反应是立体定向的，它们分别提供（E）-和（Z）-1-苯基硫烷基丁-2-烯。3-氯甲基-2，2-二甲基硫杂环丁烷和苯基锂生成3-甲基-3-苯基硫烷基丁-1-烯和3-甲基-1-苯基硫烷基丁-2-烯的混合物。在催化量的碘化亚铜（I）（10 mol％）存在下，2-氯甲基噻喃与苯基锂和甲基锂的反应导致形成取代的噻喃作为主要产物。讨论了观察到的转化的机制。
• Discovery and Lead Optimization of Benzene-1,4-disulfonamides as Oxidative Phosphorylation Inhibitors
  作者：Ding Xue、Yibin Xu、Armita Kyani、Joyeeta Roy、Lipeng Dai、Duxin Sun、Nouri Neamati

  DOI：10.1021/acs.jmedchem.1c01509

  日期：2022.1.13

  aerobic metabolism. Here, we report the discovery, optimization, and structure–activity relationship (SAR) study of a series of novel OXPHOS inhibitors. The hit compound, benzene-1,4-disulfonamide 1, was discovered in a phenotypic screen selective for cytotoxicity in a galactose-containing medium. Our multi-parameter optimization campaign led to the discovery of 65 (DX3-235), showing nanomolar inhibition

  抑制氧化磷酸化（OXPHOS）对于依赖有氧代谢的特定癌症来说是一种很有前途的治疗策略。在这里，我们报告了一系列新型 OXPHOS 抑制剂的发现、优化和构效关系 (SAR) 研究。命中化合物苯-1,4-二磺酰胺1是在含半乳糖培养基中对细胞毒性有选择性的表型筛选中发现的。我们的多参数优化活动导致了65 ( DX3-235 ) 的发现，显示了在含半乳糖的培养基中对复合物 I 功能和三磷酸腺苷 (ATP) 产生的纳摩尔抑制，从而导致显着的细胞毒性。重要的是，64 ( DX3-234) 是65的紧密类似物，在小鼠中具有良好的耐受性，并且在 Pan02 同基因胰腺癌模型中显示出显着的单药疗效，这表明高效和选择性的 OXPHOS 抑制剂可用于治疗胰腺癌。

表征谱图