2-(ethylthio)indole | 15936-38-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 2-(ethylthio)indole
• 英文别名: 2-(ethylthio)-1H-indole；2-ethylsulfanyl-1H-indole
• CAS: 15936-38-6
• 化学式: C₁₀H₁₁NS
• 分子量: 177.27
• InChiKey: YAMYNGYKAFZBTE-UHFFFAOYSA-N

物化性质

• 熔点：
  36-36.5 °C
• 沸点：
  343.9±15.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  41.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(ethylthio)indole 在 nickel(II) triflate 、 C₃₈H₅₈N₄O₄ 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 0.5h， 生成 4-(2-(ethylsulfonyl)-1H-indol-3-yl)-4-phenyl-1-(3,4,5-trimethyl-1H-pyrazol-1-yl)but-2-en-1-one
  参考文献：
  名称：

  镍（II）催化α-重氮吡唑酰胺与硫吲哚的不对称硫代克莱森重排。

  摘要：

  用修饰的手性N，N'-二氧化物配体实现了镍（II）催化的α-重氮吡唑酰胺与硫吲哚的对映体硫克莱森重排反应，高收率（高达95％）提供了多种C3取代的吲哚衍生物。在温和的反应条件下具有出色的对映选择性（高达96％ee）。基于先前的报道和催化剂的X射线晶体结构，提出了可能的过渡态模型。

  DOI：

  10.1039/d0cc04590j
• 作为产物：
  描述：

  3-(ethylsulfanyl)-1H-indole 在 三氟乙酸 作用下， 反应 2.0h， 以85%的产率得到2-(ethylthio)indole
  参考文献：
  名称：

  Plate, Ralf; Ottenheijm, Harry C. J., Tetrahedron, 1986, vol. 42, # 16, p. 4510 - 4516

  摘要：

  DOI：

文献信息

• TFA-promoted direct C–H sulfenylation at the C2 position of non-protected indoles
  作者：Thomas Hostier、Vincent Ferey、Gino Ricci、Domingo Gomez Pardo、Janine Cossy

  DOI：10.1039/c5cc05421d

  日期：——

  An efficient metal-free C–H sulfenylation process at the C2 position of non-protected indoles has been developed.

  一种高效的无金属C-H砜基化过程已经在非保护吲哚的C2位置上开发出来。
• Direct Bis-Alkyl Thiolation for Indoles with Sulfinothioates under Pummerer-Type Conditions
  作者：Peng Qi、Fang Sun、Ning Chen、Hongguang Du

  DOI：10.1021/acs.joc.1c02502

  日期：2022.1.21

  applications. This approach enabled double C–H thiolation at the C2 and C3 of the indole in one pot. The mechanism studies suggested the thiolation was realized through the sulfoxonium salt rather than sulfenyl carboxylate.

  描述了在 Pummerer 型条件下吲哚与硫代硫酸盐的无碱双烷基硫醇化反应。用 2,2,2-三氟乙酸酐活化的硫代硫酸盐被证明是一种适用于广泛应用的有效硫醇化试剂。这种方法能够在一锅中在吲哚的 C2 和 C3 上进行双 C-H 硫醇化。机理研究表明，硫醇化是通过氧化鎓盐而不是亚磺基羧酸盐实现的。
• Study on direct benzoannelations of pyrrole and indole systems by domino reactions with 4,5-dicyanopyridazine
  作者：Donatella Giomi、Marco Cecchi

  DOI：10.1016/s0040-4020(02)00958-4

  日期：2002.9

  The title pyridazine 1 was found to undergo hetero Diels–Alder [4+2] cycloadditions on the C(2)–C(3) double bond of pyrrole and indole systems; spontaneous loss of nitrogen from the primary adducts, followed by oxidation processes, afforded the corresponding fully aromatic benzoannelated skeletons in modest and reasonable yields, respectively. Competitive attacks of the same systems at the strongly

  发现标题哒嗪1在吡咯和吲哚体系的C（2）-C（3）双键上经历了杂Diels-Alder [4 + 2]环加成；初级加合物自发损失氮，然后进行氧化过程，分别以适中和合理的收率提供了相应的全芳族苯并酰胺化骨架。证明了相同系统在强亲电性C-4碳原子数为1时的竞争性攻击，这导致了取代产物的产生。
• Acid-catalyzed isomerization of 3-indolyl sulfides to 2-indolyl sulfides: first synthesis of 3-unsubstituted 2-arylthioindoles. Evidence for a complex intermolecular process
  作者：Pierre Hamel、Yves Girard、Joseph G. Atkinson

  DOI：10.1021/jo00035a029

  日期：1992.4

  The acid-catalyzed isomerization of 3-indolyl sulfides 1 to the corresponding 2-indolyl sulfides 4 provides the first synthesis of 3-unsubstituted 2-(arylthio)indoles, a hitherto unattainable class of compounds. When catalyzed by trifluoroacetic acid, the isomerization proceeds mainly via an intermolecular mechanism involving initial disproportionation to a 2,3-indolyl bis-sulfide 5 and an unsubstituted counterpart 6 followed by further interaction of these species to yield the rearranged isomer 4. A mechanism is proposed involving a role for the acid in the sulfenyl-transfer steps. This type of process also occurs, to a lesser extent, in the polyphosphoric acid catalyzed isomerization.
• Nonreductive Desulfenylation of 3-Indolyl Sulfides. Improved Syntheses of 2-Substituted Indoles and 2-Indolyl Sulfides
  作者：Pierre Hamel、Nicolas Zajac、Joseph G. Atkinson、Yves Girard

  DOI：10.1021/jo00100a045

  日期：1994.10

  Desulfenylation of 3-indolyl sulfides to the corresponding 3-unsubstituted indoles is usually carried out under reductive conditions, thus accommodating only substituents which are resistant to reduction. We have developed a nonreductive procedure for removal of a sulfide at the 3-position of indoles, using trifluoroacetic acid in the presence of a thiol as trapping agent, which is compatible with a large array of functionalities on the indole ring. In addition, the desulfenylation occurs selectively at the 3-position of the indole, and sulfide groups at other positions of the molecule remain untouched. Thus, indole 2,3-bis-sulfides are selectively desulfenylated at the 3-position, affording 3-unsubstituted 2-indolyl sulfides. This methodology broadens the use of sulfide as a protecting group for the 3-position of indoles.