α,α-dimethylindole-1-ethanol | 90901-65-8

• 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: α,α-dimethylindole-1-ethanol
• 英文别名: 1-(1H-indol-1-yl)-2-methylpropan-2-ol；1-indol-1-yl-2-methylpropan-2-ol
• CAS: 90901-65-8
• 化学式: C₁₂H₁₅NO
• 分子量: 189.257
• InChiKey: HBMZONNCGDLKAJ-UHFFFAOYSA-N

物化性质

• 沸点：
  335.6±25.0 °C(Predicted)
• 密度：
  1.04±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  25.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  α,α-dimethylindole-1-ethanol 在 tris(2,2'-bipyridyl)ruthenium dichloride 、 氧气 、 cesium acetate 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以67%的产率得到2,2-dimethyl-2,3-dihydrooxazolo[3,2-a]indol-9(9aH)-one
  参考文献：
  名称：

  Visible-light-induced aerobic dearomative reaction of indole derivatives: access to heterocycle fused or spirocyclo indolones

  摘要：

  通过可见光光催化，呈现了一种高效的吲哚脱芳香催化反应。在N1或C2位置连接的常见吲哚醇以级联反应的方式反应，提供了易于获取的多样化吲哚酮支架。

  DOI：

  10.1039/c6cc00818f
• 作为产物：
  描述：

  甲基环氧丙烷 、 吲哚 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以80%的产率得到α,α-dimethylindole-1-ethanol
  参考文献：
  名称：

  Cascade fluorofunctionalisation of 2,3-unsubstituted indoles by means of electrophilic fluorination

  摘要：

  描述了 2,3-未取代吲哚的级联氟官能化，其特点是使用 N-氟苯磺酰亚胺通过亲电氟化形成 C-C、C-F 和 C-O 键。使用与吲哚氮相连的 O-亲核试剂，可以从简单的前体合成多环氟化二氢吲哚衍生物，产率达到 40-63%。

  DOI：

  10.1039/c3cc46564k

文献信息

• Indole Syntheses Utilizing<i>o</i>-Methylphenyl Isocyanides
  作者：Yoshihiko Ito、Kazuhiro Kobayashi、Norihiko Seko、Takeo Saegusa

  DOI：10.1246/bcsj.57.73

  日期：1984.1

  New indole synthesis starting with o-methylphenyl isocyanides such as o-tolyl, 2,4-xylyl, and 2,6-xylyl isocyanide is described in full detail. Treatment of o-tolyl isocyanide with LDA in diglyme at −78 °C generated selectively o-(lithiomethyl)phenyl isocyanide in an almost quantitative yield, which on warming up to room temperature was cyclized to indole after aqueous workup. Similary, 2,4-xylyl and

  以邻甲基苯基异氰化物（例如邻甲苯基、2,4-二甲苯基和 2,6-二甲苯基异氰化物）为起始原料的新型吲哚合成得到了详细描述。在-78°C 下，在二甘醇二甲醚中用 LDA 处理邻甲苯基异氰化物，选择性地以几乎定量的产率生成邻（硫代甲基）苯基异氰化物，其在升温至室温后在水性处理后环化为吲哚。类似地，2,4-二甲苯基和2,6-二甲苯基异氰化物定量环化为5-甲基吲哚和7-甲基吲哚。邻（锂硫甲基）苯基异氰化物与诸如卤代烷和环氧烷之类的亲电子试剂反应得到邻烷基苯基异氰化物，其通过在邻苄基碳上的锂化而环化得到3-取代的吲哚。另一方面，在-78°C 下原位生成的邻（锂硫甲基）苯基异氰化物首先升温至室温，然后用亲电试剂处理以提供 1-取代的吲哚。邻（锂硫甲基）苯基异氰化物以相当好的收率与 N-酰基...
• An Orally Bioavailable, Indole-3-glyoxylamide Based Series of Tubulin Polymerization Inhibitors Showing Tumor Growth Inhibition in a Mouse Xenograft Model of Head and Neck Cancer
  作者：Helen E. Colley、Munitta Muthana、Sarah J. Danson、Lucinda V. Jackson、Matthew L. Brett、Joanne Harrison、Sean F. Coole、Daniel P. Mason、Luke R. Jennings、Melanie Wong、Vamshi Tulasi、Dennis Norman、Peter M. Lockey、Lynne Williams、Alexander G. Dossetter、Edward J. Griffen、Mark J. Thompson

  DOI：10.1021/acs.jmedchem.5b01312

  日期：2015.12.10

  A number of indole-3-glyoxylamides have previously been reported as tubulin polymerization inhibitors, although none has yet been successfully developed clinically. We report here a new series of related compounds, modified according to a strategy of reducing aromatic ring count and introducing a greater degree of saturation, which retain potent tubulin polymerization activity but with a distinct SAR from previously documented libraries. A subset of active compounds from the reported series is shown to interact with tubulin at the colchicine binding site, disrupt the cellular microtubule network, and exert a cytotoxic effect against multiple cancer cell lines. Two compounds demonstrated significant tumor growth inhibition in a mouse xenograft model of head and neck cancer, a type of the disease which often proves resistant to chemotherapy, supporting further development of the current series as potential new therapeutics.
• ARYL AND HETEROARYL ETHER COMPOUNDS AS ROR GAMMA MODULATORS
  申请人：GLENMARK PHARMACEUTICALS S.A.

  公开号：US20170022195A1

  公开（公告）日：2017-01-26

  The present disclosure is directed to compounds of formula (I) and pharmaceutically acceptable salts thereof, wherein Ring A, Ring B, R, R 2 , R 3 , n, and p are as defined herein, which are active as modulators of retinoid-related orphan receptor gamma t (RORγt). These compounds prevent, inhibit, or suppress the action of RORγt and are therefore useful in the treatment of RORγt mediated diseases, disorders, syndromes or conditions such as, e.g., pain, inflammation, COPD, asthma, rheumatoid arthritis, colitis, multiple sclerosis, psoriasis, neurodegenerative diseases and cancer.
• US9718817B2
  申请人：——

  公开号：US9718817B2

  公开（公告）日：2017-08-01