3-methyl-2-methylsulfonyl-1H-indole | 1555520-25-6

• 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: 3-methyl-2-methylsulfonyl-1H-indole
• CAS: 1555520-25-6
• 化学式: C₁₀H₁₁NO₂S
• 分子量: 209.269
• InChiKey: JFJNJECMOTYPOU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  58.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-甲基吲哚 、 sodium methansulfinate 在 碘 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以30%的产率得到3-methyl-2-methylsulfonyl-1H-indole
  参考文献：
  名称：

  Regioselective C2 Sulfonylation of Indoles Mediated by Molecular Iodine

  摘要：

  A facile and general method for regioselective C2 sulfonylation reaction of indoles mediated by iodine is described. The 2-sulfonylated products were obtained up to 96% yield under mild reaction conditions (room temperature, 2 h).

  DOI：

  10.1021/jo402831k

文献信息

• Endothelin antagonistic substance
  申请人：BANYU PHARMACEUTICAL CO., LTD.

  公开号：EP0555537A2

  公开（公告）日：1993-08-18

  A peptide derivative of the formula: wherein A is a group of the formula R"O-CO- (wherein R11 is a lower alkyl group or a phenyl group), or a group of the formula R12R13N-C(=O)- (wherein R12 is a lower alkyl group, a cycloalkyl group, a 1-adamantyl group, a phenyl group wherein one or two optional hydrogen atoms on the benzene ring may independently be replaced by a halogen atom, a trifluoromethyl group, a nitro group, an amino group or a formylamino group, a pyridyl group, or a thienyl group, R13 is a hydrogen atom, a lower alkyl group or a cycloalkyl group, or R12 and R13 form, together with the adjacent nitrogen atom, a 5- to 9-membered nitrogen-containing saturated heterocyclic ring having 4 to 8 carbon atoms, wherein among methylene groups forming the ring, one optional methylene group not adjacent to the above nitrogen atom may be replaced by a thio group, and one to four optional hydrogen atoms on the carbon atoms of the heterocyclic ring may independently be replaced by a lower alkyl group, and further two adjacent carbon atoms in the heterocyclic ring may form a benzo-fused ring); B is an oxygen atom or a group of the formula -NR2- (wherein R2 is a hydrogen atom or a lower alkyl group); R3 is a lower alkyl group, a cycloalkyl group, an aryl group, a heterocyclic group, a cycloalkyl lower alkyl group, an aryl lower alkyl group or a heterocyclic lower alkyl group; X1 is an oxygen atom or a group of the formula -NR4- (wherein R4 is a hydrogen atom or a lower alkyl group); R5 is a 3-indolylmethyl, 3-benzothienylmethyl, 1-naphthylmethyl or benzyl group wherein one or two optional hydrogen atoms on the ring may be replaced by a hydroxyl group, a halogen atom, a formyl group, a lower alkyl group, a lower alkoxy group, a lower alkylthio group, a lower alkylsulfinyl group, a lower alkylsulfonyl group, a lower alkoxycarbonyl group, a nitro group or a group of the formula R51-CO-X-2 wherein R51 is a lower alkyl group, a lower alkoxy group, or an amino group which may be substituted by a lower alkyl group, and X2 is an oxygen atom or a group of the formula -NR52- (wherein R52 is a hydrogen atom or a lower alkyl group)}; X3 is an oxygen atom or a sulfur atom; R6 is a hydrogen atom, or a lower alkyl or lower alkenyl group which may have a substituent selected from the group consisting of a hydroxyl group, a lower alkoxy group, a lower alkylthio group and a heterocyclic group; n is 0 or 1; Y is a hydroxymethyl group, a group of the formula CO2R71 (wherein R71 is a hydrogen atom or a lower alkyl group), a group of the formula CONHR72 (wherein R72 is a hydrogen atom or a lower alkyl group which may have a substituent selected from the group consisting of a hydroxyl group, a carboxyl group and a sulfo group), a 1 H-tetrazol-5-yl group, a sulfo group and a phosphono group; or a pharmaceutically acceptable salt thereof.

  式中的肽衍生物： 其中 A 是式 R "O-CO- 的基团（其中 R11 是低级烷基或苯基），或式 R12R13N-C(=O)- 的基团（其中 R12 是低级烷基、环烷基、1-金刚烷基、苯基，其中苯环上的一个或两个任选氢原子可独立地被卤素原子、三氟甲基、硝基、氨基或甲酰氨基、吡啶基或噻吩基取代，R13 是氢原子、低级烷基或环烷基、或 R12 和 R13 与相邻的氮原子一起形成具有 4 至 8 个碳原子的 5 至 9 元含氮饱和杂环，其中在形成环的亚甲基中，不与上述氮原子相邻的一个任选亚甲基可被硫代基团取代，杂环碳原子上的 1 至 4 个任选氢原子可独立地被低级烷基取代，杂环中的另外两个相邻碳原子可形成苯并融合环），R12 和 R13 与相邻的氮原子一起形成具有 4 至 8 个碳原子的 5 至 9 元含氮饱和杂环，其中在形成环的亚甲基中，不与上述氮原子相邻的一个任选亚甲基可被硫代基团取代，杂环碳原子上的 1 至 4 个任选氢原子可独立地被低级烷基取代，杂环中的另外两个相邻碳原子可形成苯并融合环）；B 是氧原子或式-NR2-的基团（其中 R2 是氢原子或低级烷基）； R3 是低级烷基、环烷基、芳基、杂环基、环烷基低级烷基、芳基低级烷基或杂环低级烷基； X1 是氧原子或式-NR4-的基团（其中 R4 是氢原子或低级烷基）；R5是3-吲哚甲基、3-苯并噻吩甲基、1-萘甲基或苄基，其中环上的一个或两个任选氢原子可被羟基、卤素原子、甲酰基、低级烷基、低级烷氧基、低级烷硫基、低级烷基亚磺酰基、低级烷基磺酰基取代、低级烷氧基羰基、硝基或式 R51-CO-X-2 的基团其中 R51 为低级烷基、低级烷氧基或可被低级烷基取代的氨基，X2 为氧原子或式 -NR52- 的基团（其中 R52 为氢原子或低级烷基）}；X3 是氧原子或硫原子；R6 是氢原子，或低级烷基或低级烯基，其取代基可选自由羟基、低级烷氧基、低级烷硫基和杂环基组成的组；n 是 0 或 1；Y 是羟甲基、式 CO2R71 的基团（其中 R71 是氢原子或低级烷基）、式 CONHR72 的基团（其中 R72 是氢原子或低级烷基，其取代基可选自由羟基、羧基和磺基组成的组）、1H-四唑-5-基、磺基和膦基；或其药学上可接受的盐。
• US5496928A
  申请人：——

  公开号：US5496928A

  公开（公告）日：1996-03-05
• Regioselective <i>C</i>2 Sulfonylation of Indoles Mediated by Molecular Iodine
  作者：Praewpan Katrun、Charoensak Mueangkaew、Manat Pohmakotr、Vichai Reutrakul、Thaworn Jaipetch、Darunee Soorukram、Chutima Kuhakarn

  DOI：10.1021/jo402831k

  日期：2014.2.21

  A facile and general method for regioselective C2 sulfonylation reaction of indoles mediated by iodine is described. The 2-sulfonylated products were obtained up to 96% yield under mild reaction conditions (room temperature, 2 h).