tert-butyl 3-(3-iodopropyl)indole-1-carboxylate | 141972-28-3

• 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: tert-butyl 3-(3-iodopropyl)indole-1-carboxylate
• 英文别名: 3-(3-iodo-propyl)-indole-1-carboxylic acid tert-butyl ester；t-butyl 3-(3-iodopropyl)-1H-indole-1-carboxylate；Tert-butyl 3-(3-iodopropyl)-1h-indole-1-carboxylate
• CAS: 141972-28-3
• 化学式: C₁₆H₂₀INO₂
• 分子量: 385.245
• InChiKey: BHLJXUKFZDBWSY-UHFFFAOYSA-N

物化性质

• 沸点：
  431.2±47.0 °C(Predicted)
• 密度：
  1.43±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  31.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  tert-butyl 3-(3-iodopropyl)indole-1-carboxylate 在 lithium cyclohexylisopropylamide 作用下， 以 乙腈 为溶剂， 反应 2.67h， 生成 ethyl 2-chloro-5-(indol-3'-yl)pent-2-enoate
  参考文献：
  名称：

  Synthesis of 3,4-bridged indoles by photocyclisation reactions. Part 2. Photocyclisation of halogenoacetyl tryptophol derivatives and α-chloro indol-3-ylalkanoate esters

  摘要：

  Irradiation of the trichloroacetates 2, 4 and 5, derived from the corresponding tryptophols, in methanolic acetonitrile results in photocyclisation to the indole 4-position, and the formation of the pyrrolobenzoxocines 9-11. Attempted photocyclisation of the 'reversed' alpha-chloro esters 15a, 15b and 18 was thwarted by readily occurring elimination of HCl, although the dimethyl compound 15c did cyclise to give the cycloheptaindole 20 upon irradiation in acetonitrile.

  DOI：

  10.1039/p19920000813
• 作为产物：
  描述：

  3-(1H-indol-3-yl)propyl 4-methylbenzenesulfonate 在 4-二甲氨基吡啶 、 sodium iodide 作用下， 以 丙酮 、 乙腈 为溶剂， 反应 63.0h， 生成 tert-butyl 3-(3-iodopropyl)indole-1-carboxylate
  参考文献：
  名称：

  Synthesis of 3,4-bridged indoles by photocyclisation reactions. Part 2. Photocyclisation of halogenoacetyl tryptophol derivatives and α-chloro indol-3-ylalkanoate esters

  摘要：

  Irradiation of the trichloroacetates 2, 4 and 5, derived from the corresponding tryptophols, in methanolic acetonitrile results in photocyclisation to the indole 4-position, and the formation of the pyrrolobenzoxocines 9-11. Attempted photocyclisation of the 'reversed' alpha-chloro esters 15a, 15b and 18 was thwarted by readily occurring elimination of HCl, although the dimethyl compound 15c did cyclise to give the cycloheptaindole 20 upon irradiation in acetonitrile.

  DOI：

  10.1039/p19920000813

文献信息

• Copper-Catalyzed Reductive Trifluoromethylation of Alkyl Iodides with Togni’s Reagent
  作者：Yanchi Chen、Guobin Ma、Hegui Gong

  DOI：10.1021/acs.orglett.8b02005

  日期：2018.8.3

  This work illustrates a reductive cross-electrophile coupling protocol for trifluoromethylation of alkyl iodides under Cu-catalyzed/Ni-promoted reaction conditions. The use of diboron esters as the terminal reductant allows the effective generation of the alkyl–CF3 products with excellent functional group tolerance and broad substrate scope. A mechanism involving a reaction of alkyl–Cu with Togni’s

  这项工作说明了在Cu催化/ Ni促进的反应条件下烷基碘的三氟甲基化的还原性交亲电子偶联方案。使用二硼酸酯作为末端还原剂可以有效生成具有出色的官能团耐受性和广泛的底物范围的烷基-CF 3产物。提出了一种涉及烷基铜与Togni试剂反应的机理。
• POLYCYCLIC ACID COMPOUNDS USEFUL AS CRTH2 ANTAGONISTS AND ANTIALLERGIC AGENTS
  申请人：Terasaka Tadashi

  公开号：US20100009991A1

  公开（公告）日：2010-01-14

  The present invention relates to a novel compound or a salt thereof, which is useful as a CRTH2 antagonist, especially as a medicament for disorder that participates eosinophil, for example, allergic disorder such as asthma, allergic rhinitis, allergic dermatitis, conjunctival inflammation, hives, eosinophilic bronchitis, food allergy, inflammation of the nasal sinuses, multiple sclerosis, angiitis, or chronic obstructive pulmonary disease (COPD) and the like.

  本发明涉及一种新型化合物或其盐，该化合物可作为CRTH2拮抗剂使用，特别是作为治疗参与嗜酸性粒细胞的疾病的药物，例如哮喘、过敏性鼻炎、过敏性皮炎、结膜炎、荨麻疹、嗜酸性支气管炎、食物过敏、鼻窦炎炎症、多发性硬化症、血管炎或慢性阻塞性肺疾病（COPD）等疾病。
• Polycyclic acid compounds useful as CRTH2 antagonists and antiallergic agents
  申请人：Astellas Pharma Inc

  公开号：US08273745B2

  公开（公告）日：2012-09-25

  The present invention relates to a novel compound or a salt thereof, which is useful as a CRTH2 antagonist, especially as a medicament for disorder that participates eosinophil, for example, allergic disorder such as asthma, allergic rhinitis, allergic dermatitis, conjunctival inflammation, hives, eosinophilic bronchitis, food allergy, inflammation of the nasal sinuses, multiple sclerosis, angiitis, or chronic obstructive pulmonary disease (COPD) and the like.

  本发明涉及一种新型化合物或其盐，其作为CRTH2拮抗剂具有用途，特别是作为参与嗜酸性粒细胞的疾病的药物，例如过敏性疾病，如哮喘，过敏性鼻炎，过敏性皮炎，结膜炎，荨麻疹，嗜酸性支气管炎，食物过敏，鼻窦炎炎症，多发性硬化症，血管炎或慢性阻塞性肺疾病（COPD）等。
• Thornton, Aaron R.; Martin, Veronique I.; Blakey, Simon B., Journal of the American Chemical Society, 2009, vol. 131, p. 2434 - 2435
  作者：Thornton, Aaron R.、Martin, Veronique I.、Blakey, Simon B.

  DOI：——

  日期：——
• US8273745B2
  申请人：——

  公开号：US8273745B2

  公开（公告）日：2012-09-25