2-<(4-methoxyphenyl)thio>indole | 139461-66-8

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-<(4-methoxyphenyl)thio>indole
• 英文别名: 2-(4-methoxyphenyl)sulfanyl-1H-indole
• CAS: 139461-66-8
• 化学式: C₁₅H₁₃NOS
• 分子量: 255.34
• InChiKey: UXSYPXUFBSHOTG-UHFFFAOYSA-N

物化性质

• 沸点：
  471.2±25.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 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：
  50.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-<(4-methoxyphenyl)thio>indole 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 生成 2-((4-methoxyphenyl)sulfonyl)-1H-indole
  参考文献：
  名称：

  新型醛糖还原酶抑制剂的设计合成和评估：以吲哚基-磺酰基-酚为例。

  摘要：

  醛糖还原酶抑制剂的治疗性干预似乎是治疗主要病理状况（即与慢性高血糖症，慢性炎症和癌症有关的神经病变/血管病）的一种有前途的方法。到目前为止，最有效的醛糖还原酶抑制剂是羧酸衍生物，其渗透性差。在这项工作中，继续我们以前的工作，我们促进了羧酸部分的生物等位取代，以制造同样有效但更具药物作用的抑制剂。

  DOI：

  10.1016/j.bmc.2020.115575
• 作为产物：
  描述：

  4,4'-二甲氧基二苯二硫 在 磺酰氯 、 硫代水杨酸 作用下， 以 三氟乙酸 为溶剂， 反应 1.58h， 生成 2-<(4-methoxyphenyl)thio>indole
  参考文献：
  名称：

  Nonreductive Desulfenylation of 3-Indolyl Sulfides. Improved Syntheses of 2-Substituted Indoles and 2-Indolyl Sulfides

  摘要：

  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.

  DOI：

  10.1021/jo00100a045

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。
• Copper-catalyzed synthesis of 2-sulfenylindoles from indoline-2-thiones and aryl iodides
  作者：Shiping Zhou、Genhua Xiao、Yun Liang

  DOI：10.1016/j.tetlet.2016.12.028

  日期：2017.1

  A novel and efficient method for synthesis of 2-sulfenylindole via copper-catalyzed coupling reaction of indoline-2-thiones with aryl iodides has been developed. A series of N-substituted and N-free 2-sulfenylindole were obtained in high yields. Furthermore, the method was employed to synthesis of benzothieno[2,3-b]indoles from indoline-2-thiones with 1,2-diiodobenzene in the presence of CuI and Pd(OAc)2

  通过铜催化的吲哚-2-硫酮与芳基碘的偶联反应合成2-亚磺酰基吲哚的新方法已经得到了发展。以高收率获得了一系列的N-取代的和不含N的2-亚磺酰基吲哚。此外，该方法用于在CuI和Pd（OAc）2作为催化剂存在下，由吲哚啉-2-硫酮与1,2-二碘代苯合成苯并噻吩并[2,3- b ]吲哚。
• Regioselective Synthesis of Mixed Indole 2,3-Bis(sulfides). A Study of the Mechanism of the Second Sulfenylation of Indole
  作者：Pierre Hamel、Patrice Préville

  DOI：10.1021/jo951420n

  日期：1996.1.1

  Sulfenylation of indole using sulfenyl chlorides leads to the initial formation of a 3-indolyl sulfide, while excess reagent introduces a second sulfide at the 2-position of the ring. The mechanism of this second sulfenylation has not, to date, been rigorously elucidated. The development of the first, regioselective synthesis of mixed indole 2,3-bis(sulfides) has allowed the study of the sulfenylation

  使用亚磺酰氯进行吲哚的亚磺酰化会导致3-吲哚基硫化物的初步形成，而过量的试剂会在环的2-位引入第二个硫化物。迄今为止，尚未明确阐明第二次亚磺酰化的机理。混合吲哚2，3-双（硫化物）的第一个区域选择性合成的发展已经允许使用不同的亚磺酰氯进行3-吲哚基硫化物的亚磺酰基化的研究。我们的结果提供了证据，表明该反应是通过中间体3,3-二硫代化的吲哚烯进行的，随后其中一个硫化物基团迁移到了2位。
• 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.
• Hamel Pierre, Zajac Nicolas, Atkinson Joseph G., Girard Yves, J. Org. Chem, 59 (1994) N 21, S 6372-6377
  作者：Hamel Pierre, Zajac Nicolas, Atkinson Joseph G., Girard Yves

  DOI：——

  日期：——