(吲哚-3-基硫代)乙腈 | 61021-51-0

• 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
• 中文名称: (吲哚-3-基硫代)乙腈
• 英文名称: 2-((1H-indol-3-yl)thio)acetonitrile
• 英文别名: (indol-3-ylthio)acetonitrile；3-indolylthioacetonitrile；Acetonitrile, (1H-indol-3-ylthio)-；2-(1H-indol-3-ylsulfanyl)acetonitrile
• CAS: 61021-51-0
• 化学式: C₁₀H₈N₂S
• mdl: MFCD00297150
• 分子量: 188.253
• InChiKey: NYJACYLXVJMNOM-UHFFFAOYSA-N

物化性质

• 熔点：
  52-54.5°C

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  64.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (吲哚-3-基硫代)乙腈 在 sodium hydroxide 、 三氟化硼四氢呋喃络合物 、 苄基三乙基氯化铵 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 18.0h， 生成 2-[1-[(E)-3-phenylprop-2-enyl]indol-3-yl]sulfanylethanamine
  参考文献：
  名称：

  Cardiac-slowing amidines containing the 3-thioindole group. Potential antianginal agents

  摘要：

  A series of 3-thioindolamidines (and 3-indolamidines) related to mixidine (1) was studied for cardiac-slowing properties, following the discovery of activity for prototype thioindole 2. Structure-activity relationships were explored, leading to many potent antitachycardiac agents (6-9, 12, 13, 15-17, 20, 23, 24, 30, 34, 35, 45, and 47-49). Relative to 2, cardiac-slowing activity is enhanced by substitution of the indole nitrogen with small (C1-C3) saturated alkyl groups (6-9), unsaturated alkyl groups (12, 13, and 15-17), or a methoxyethyl group (20); replacement of the N-methyl group with alkyl (23) or phenyl groups (24); and extension of the ethylene bridge by two methylene units (34). Dethio (i.e., 3-indole) analogues of 2 with alkyl substitution on the indole nitrogen (47-49) have greater activity as well. Several potent compounds were also found to have minimal myocardial depression (6-9, 13, 45, and 47). Secondary pharmacological testing is reported for thioindoles 2, 6, 7, 9, and 28.

  DOI：

  10.1021/jm00356a021
• 作为产物：
  描述：

  吲哚 、 sodium S-(cyanomethyl) sulfothioate 在 四丁基碘化铵 作用下， 以 1,2-二氯乙烷 为溶剂， 以85%的产率得到(吲哚-3-基硫代)乙腈
  参考文献：
  名称：

  四正丁基碘化铵介导的吲哚与班特盐的反应：在无金属和无氧化剂的条件下，吲哚的有效3-亚磺酰化†

  摘要：

  证明了一种高效的四正丁基碘化铵（TBAI）引发的用布恩特盐将吲哚进行3-磺酰化的方法。该方案提供了一种简单的策略，可以在无金属和无氧化剂的条件下，由相应的吲哚制备3-烷基硫代吲哚和3-芳基硫代吲哚。

  DOI：

  10.1039/c6ob01528j

文献信息

• Substituted indoles
  申请人：McNeil Laboratories, Incorporated

  公开号：US04059583A1

  公开（公告）日：1977-11-22

  Substituted thioindoles and their sulfoxide and sulfone derivatives, useful as cardiac rate lowering agents and for other pharmacological properties, and precursors therefor.

  替代硫代吲哚及其亚砜和砜氧化物衍生物，可用作心脏降速剂和具有其他药理特性，以及它们的前体。
• Chiral Phosphoric Acid‐Catalyzed Chemo‐ and Enantioselective N‐Alkylation of Indoles with Imines
  作者：Shuyuan Yang、Linger Li、Junling Zhao

  DOI：10.1002/adsc.202201077

  日期：2022.12.8

  A chemo- and enantioselective protocol for the N-alkylation of indoles with imines was developed. This process was catalyzed by a BINOL-derived phosphoric acid catalyst to give the corresponding acyclic aminals of indoles in 46–99% yields with 70–98% ee. The application of this method for the “late-stage” functionalization of a bioactive compound was performed with high efficency. The products showed

  开发了用亚胺对吲哚进行 N-烷基化的化学和对映选择性方案。该过程由 BINOL 衍生的磷酸催化剂催化，以 46-99% 的产率和 70-98% ee 得到相应的吲哚无环缩醛胺。该方法用于生物活性化合物“后期”功能化的应用效率很高。产品表现出良好的稳定性，并可以进行许多进一步的转化。
• ZELESKO, M. J.;MCCOMSEY, D. F.;HAGEMAN, W. E.;NORTEY, S. O.;BAKER, C. A.;+, J. MED. CHEM., 1983, 26, N 2, 230-237
  作者：ZELESKO, M. J.、MCCOMSEY, D. F.、HAGEMAN, W. E.、NORTEY, S. O.、BAKER, C. A.、+

  DOI：——

  日期：——
• US4059583A
  申请人：——

  公开号：US4059583A

  公开（公告）日：1977-11-22
• Cardiac-slowing amidines containing the 3-thioindole group. Potential antianginal agents
  作者：Michael J. Zelesko、David F. McComsey、William E. Hageman、Samuel O. Nortey、Carol A. Baker、Bruce E. Maryanoff

  DOI：10.1021/jm00356a021

  日期：1983.2

  A series of 3-thioindolamidines (and 3-indolamidines) related to mixidine (1) was studied for cardiac-slowing properties, following the discovery of activity for prototype thioindole 2. Structure-activity relationships were explored, leading to many potent antitachycardiac agents (6-9, 12, 13, 15-17, 20, 23, 24, 30, 34, 35, 45, and 47-49). Relative to 2, cardiac-slowing activity is enhanced by substitution of the indole nitrogen with small (C1-C3) saturated alkyl groups (6-9), unsaturated alkyl groups (12, 13, and 15-17), or a methoxyethyl group (20); replacement of the N-methyl group with alkyl (23) or phenyl groups (24); and extension of the ethylene bridge by two methylene units (34). Dethio (i.e., 3-indole) analogues of 2 with alkyl substitution on the indole nitrogen (47-49) have greater activity as well. Several potent compounds were also found to have minimal myocardial depression (6-9, 13, 45, and 47). Secondary pharmacological testing is reported for thioindoles 2, 6, 7, 9, and 28.