6-(phenylthio)benzo[1,3]dioxole-5-carbaldehyde | 158719-70-1

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 6-(phenylthio)benzo[1,3]dioxole-5-carbaldehyde
• 英文别名: 6-Phenylsulfanyl-1,3-benzodioxole-5-carbaldehyde
• CAS: 158719-70-1
• 化学式: C₁₄H₁₀O₃S
• 分子量: 258.298
• InChiKey: ICBBSDVETAURBD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  60.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-(phenylthio)benzo[1,3]dioxole-5-carbaldehyde 在 sodium tetrahydroborate 作用下， 以 吡啶 为溶剂， 反应 5.0h， 生成 2,2,2-Trifluoro-N-[2-(4-hydroxy-phenyl)-ethyl]-N-(6-phenylsulfanyl-benzo[1,3]dioxol-5-ylmethyl)-acetamide
  参考文献：
  名称：

  Oxidative Intramolecular Phenolic Coupling Reaction Induced by a Hypervalent Iodine(III) Reagent:  Leading to Galanthamine-Type Amaryllidaceae Alkaloids

  摘要：

  By extending our oxidative phenol-coupling reactions using a hypervalent iodine(III) reagent, a versatile synthetic procedure for the galanthamine-type Amaryllidaceae alkaloids was accomplished. The first total synthesis of (+/-)-sanguinine and the total syntheses of (+/-)-galanthamine, (+/-)-narwedine, (+/-)-lycoramine, and (+/-)-norgalanthamine were also successfully carried out.

  DOI：

  10.1021/jo9807868
• 作为产物：
  描述：

  苯基硫三甲基硅烷 、 6-硝基胡椒醛 在 四丁基氟化铵 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以93%的产率得到6-(phenylthio)benzo[1,3]dioxole-5-carbaldehyde
  参考文献：
  名称：

  在温和和中性条件下，通过TBAF介导的硝基芳烃用PhSTMS的硝基芳烃的反硝化取代，可有效合成不对称的二芳基硫醚

  摘要：

  摘要氟化四丁基铵（TBAF）在温和且无碱的中性条件下，在室温下有效地促进了缺电子硝基芳烃与苯基硫代三甲基硅烷（PhSTMS）的反硝化取代反应，为实用，有效地合成有用的不对称二芳基硫醚提供了可能。带有邻位和对位吸电子基团的硝基芳烃是反应性最高的底物，表明该反应最有可能通过亲核芳族取代（SN Ar）机理进行。

  DOI：

  10.1016/j.cclet.2013.04.011

文献信息

• Regioselective Cleavage Reaction of the Aromatic Methylenedioxy Ring. VI. Synthesis of Phenothiazine Analogues by Using the Cleavage Reaction with Sodium Methoxide-Thiols in Dimethyl Sulfoxide and Evaluation of Their Biological Activities.
  作者：Yasuhiro IMAKURA、Tatsuya KONISHI、Kazuiti UCHIDA、Hiromu SAKURAI、Shigeru KOBAYASHI、Akihiro HARUNO、Kiyotaka TAJIMA、Shinsuke YAMASHITA

  DOI：10.1248/cpb.42.500

  日期：——

  prepared from the 4-hydroxybenzene derivatives and their Ca2+ antagonistic activities were evaluated. Among these compounds, 2-(2-bromophenylthiomethoxy)-10-(2-diethylaminoacetyl)-3- methoxyphenothiazine (46) showed the most potent Ca2+ antagonistic activity. Biological activity could be conveniently evaluated by measurement of the peak height of the vanadyl ion (+4 oxidation ion) signal produced by

  含吸电子基团的芳族亚甲二氧基化合物与甲醇钠-硫醇在二甲亚砜中的反应通过硫醇盐离子对亚甲二氧基环的区域选择性攻击而以良好的产率得到了3-和4-羟基苯衍生物。讨论了亚甲二氧基环裂解反应中硫醇根离子的形成机理和反应性。从4-羟基苯衍生物制备了各种生物活性化合物32a，32d，36b，38b，41b和44-47，并评估了其对Ca2 +的拮抗活性。在这些化合物中，2-（2-溴苯硫基甲氧基）-10-（2-二乙基氨基乙酰基）-3-甲氧基吩噻嗪（46）显示出最有效的Ca2 +拮抗活性。
• Efficient synthesis of unsymmetrical diaryl thioethers via TBAF-mediated denitrative substitution of nitroarenes with PhSTMS under mild and neutral conditions
  作者：Xiao-Chun Yu、Bo Li、Bao-Hua Yu、Qing Xu

  DOI：10.1016/j.cclet.2013.04.011

  日期：2013.7

  Abstract Tetrabutylammonium fluoride (TBAF) effectively facilitated a denitrative substitution reaction of electron-deficient nitroarenes with phenylthiotrimethylsilane (PhSTMS) under mild and base-free neutral conditions at room temperature, providing a practical and efficient synthesis of useful unsymmetrical diaryl thioethers. Nitroarenes bearing ortho- and para -positioned electron-withdrawing groups

  摘要氟化四丁基铵（TBAF）在温和且无碱的中性条件下，在室温下有效地促进了缺电子硝基芳烃与苯基硫代三甲基硅烷（PhSTMS）的反硝化取代反应，为实用，有效地合成有用的不对称二芳基硫醚提供了可能。带有邻位和对位吸电子基团的硝基芳烃是反应性最高的底物，表明该反应最有可能通过亲核芳族取代（SN Ar）机理进行。
• Oxidative Intramolecular Phenolic Coupling Reaction Induced by a Hypervalent Iodine(III) Reagent:  Leading to Galanthamine-Type Amaryllidaceae Alkaloids
  作者：Yasuyuki Kita、Mitsuhiro Arisawa、Michiyo Gyoten、Makiko Nakajima、Ryuji Hamada、Hirofumi Tohma、Takeshi Takada

  DOI：10.1021/jo9807868

  日期：1998.9.1

  By extending our oxidative phenol-coupling reactions using a hypervalent iodine(III) reagent, a versatile synthetic procedure for the galanthamine-type Amaryllidaceae alkaloids was accomplished. The first total synthesis of (+/-)-sanguinine and the total syntheses of (+/-)-galanthamine, (+/-)-narwedine, (+/-)-lycoramine, and (+/-)-norgalanthamine were also successfully carried out.