5-methoxy-2,3,4,9-tetrahydro-1H-carbazol-1-one | 41084-54-2

• 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: 5-methoxy-2,3,4,9-tetrahydro-1H-carbazol-1-one
• 英文别名: 5-Methoxy-3,4-dihydrocarbazol-1-(2H)-on；5-methoxy-2,3,4,9-tetrahydro-carbazol-1-one；5-Methoxy-2,3,4,9-tetrahydrocarbazol-1-one；5-methoxy-2,3,4,9-tetrahydrocarbazol-1-one
• CAS: 41084-54-2
• 化学式: C₁₃H₁₃NO₂
• 分子量: 215.252
• InChiKey: KDBHIAZHUMBEFQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  42.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-methoxy-2,3,4,9-tetrahydro-1H-carbazol-1-one 、 三甲基乙炔基硅 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.0h， 以77%的产率得到5-methoxy-1-((trimethylsilyl)ethynyl)-2,3,4,9-tetrahydro-1H-carbazol-1-ol
  参考文献：
  名称：

  手性布朗斯台德酸催化外消旋吲哚甲醇合成手性四氢咔唑与烯基硅烷

  摘要：

  公开了一种合成含有丙二烯部分的手性四氢咔唑 (THC) 的有效方法，该方法是通过手性磷酸催化的对映收敛取代反应建立的。在 SPINOL 衍生的手性磷酸存在下，带有 THC 基序的外消旋吲哚甲醇与N-甲基吡咯反应，以良好的收率和高对映选择性得到相应的手性 THCs。

  DOI：

  10.1246/cl.210803
• 作为产物：
  描述：

  2-(羟基亚甲基)环己酮 在 盐酸 、 硫酸 、 sodium nitrite 作用下， 以 水 、 乙腈 为溶剂， 生成 5-methoxy-2,3,4,9-tetrahydro-1H-carbazol-1-one 、 7-Methoxy-1-oxo-1,2,3,4-tetrahydro-carbazol
  参考文献：
  名称：

  A novel necroptosis inhibitor—necrostatin-21 and its SAR study

  摘要：

  An initial structure-activity relationship study of the novel necroptosis inhibitor Nec-21 was described. Any changes of the tetracyclic scaffold were detrimental for the activity. Introduction of a substituent to 7 or 8 position (e.g., cyano or methoxy group, respectively), would increase the activity. The 7 and 8-position disubstituted compound 17b was 35-fold as potent as the lead, while EC50 reached 14 nM. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.06.073

文献信息

• Chakraborty, Suchandra; Chattopadhyay, Gautam; Saha, Chandan, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2011, vol. 50, # 2, p. 201 - 206
  作者：Chakraborty, Suchandra、Chattopadhyay, Gautam、Saha, Chandan

  DOI：——

  日期：——
• Synthesis of substituted tetrahydron-1H-carbazol-1-one and analogs via PhI(OCOCF3)2-mediated oxidative C–C bond formation
  作者：Hao Shi、Tianjian Guo、Daisy Zhang-Negrerie、Yunfei Du、Kang Zhao

  DOI：10.1016/j.tet.2014.02.083

  日期：2014.4

  A variety of tetrahydro-1H-carbazol-1-ones and analogs were conveniently synthesized from the reaction of the corresponding 2-(phenylamino)cyclohex-2-enone with hypervalent iodine reagent PhI(OCOCF3)2 (FIFA), through a direct intramolecular oxidative C(sp(2))-C(sp(2)) bond formation. This approach realized the construction of the biologically important tetrahydro-1H-carbazol-1-one and tetrahydrocyclohepta[b]lindol-6(5H)-one skeletons. The mechanism of the process was proposed and briefly discussed. (C) 2014 Elsevier Ltd. All rights reserved.
• A novel necroptosis inhibitor—necrostatin-21 and its SAR study
  作者：Zhijie Wu、Ying Li、Yu Cai、Junying Yuan、Chengye Yuan

  DOI：10.1016/j.bmcl.2013.06.073

  日期：2013.9

  An initial structure-activity relationship study of the novel necroptosis inhibitor Nec-21 was described. Any changes of the tetracyclic scaffold were detrimental for the activity. Introduction of a substituent to 7 or 8 position (e.g., cyano or methoxy group, respectively), would increase the activity. The 7 and 8-position disubstituted compound 17b was 35-fold as potent as the lead, while EC50 reached 14 nM. (C) 2013 Elsevier Ltd. All rights reserved.
• Chiral Brønsted Acid Catalyzed Enantioconvergent Synthesis of Chiral Tetrahydrocarbazoles with Allenylsilanes from Racemic Indolylmethanols
  作者：Shigenobu Umemiya、Kong Lingqi、Yuno Eto、Masahiro Terada

  DOI：10.1246/cl.210803

  日期：2022.4.5

  An efficient method for the synthesis of chiral tetrahydrocarbazoles (THCs) containing an allene moiety is disclosed, which was established by an enantioconvergent substitution reaction catalyzed by a chiral phosphoric acid. Racemic indolylmethanols bearing the THC motif reacted with N-methylpyrrole in the presence of the SPINOL-derived chiral phosphoric acid to give the corresponding chiral THCs with

  公开了一种合成含有丙二烯部分的手性四氢咔唑 (THC) 的有效方法，该方法是通过手性磷酸催化的对映收敛取代反应建立的。在 SPINOL 衍生的手性磷酸存在下，带有 THC 基序的外消旋吲哚甲醇与N-甲基吡咯反应，以良好的收率和高对映选择性得到相应的手性 THCs。