5,6-dimethyl-2,3-dihydro-1H-indole | 791609-49-9

• 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: 5,6-dimethyl-2,3-dihydro-1H-indole
• 英文别名: dimethylindoline；5,6-dimethylindoline；1H-Indole, 2,3-dihydro-5,6-dimethyl-
• CAS: 791609-49-9
• 化学式: C₁₀H₁₃N
• mdl: MFCD19218809
• 分子量: 147.22
• InChiKey: ISDNDQYXHHLGQN-UHFFFAOYSA-N

物化性质

• 熔点：
  35-38 °C (decomp)
• 沸点：
  258.9±40.0 °C(Predicted)
• 密度：
  1.000±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5,6-dimethyl-2,3-dihydro-1H-indole 在 正丁基锂 、 2-氟-1-甲基吡啶翁对甲苯磺酸盐 、 N,N-二异丙基乙胺 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 25.0h， 生成 1-(5-O-triphenylmethyl-2,3-O-isopropylidene-α-D-ribofuranosyl) 5,6-dimethylindoline
  参考文献：
  名称：

  Regioselective Glycosylation: Synthesis of α-Indoline Nucleosides

  摘要：

  Novel indoline ribonucleosides with the alpha-N-glycoside configuration are synthesized with very high regioselectivily in 90-96% yield, using TMS protected indolines and 2,3-O-(1-methylethylidene)-5-O-(triphenylmethyl)-alpha/beta-D-ribofuranose. The structures of these ribonucleosides were elucidated with X-ray crystallography as well as 2D (NOESY COSY and HMQC) NMR spectroscopy.

  DOI：

  10.1081/ncn-200067398
• 作为产物：
  描述：

  N-(2,4,5-三甲基苯基)甲酰胺 在 potassium tert-butylate 、 sodium cyanoborohydride 、 溶剂黄146 作用下， 反应 2.0h， 生成 5,6-dimethyl-2,3-dihydro-1H-indole
  参考文献：
  名称：

  Regioselective Glycosylation: Synthesis of α-Indoline Nucleosides

  摘要：

  Novel indoline ribonucleosides with the alpha-N-glycoside configuration are synthesized with very high regioselectivily in 90-96% yield, using TMS protected indolines and 2,3-O-(1-methylethylidene)-5-O-(triphenylmethyl)-alpha/beta-D-ribofuranose. The structures of these ribonucleosides were elucidated with X-ray crystallography as well as 2D (NOESY COSY and HMQC) NMR spectroscopy.

  DOI：

  10.1081/ncn-200067398

文献信息

• Low temperature dehydrogenation of α-indoline nucleosides
  作者：Tilak Chandra、Shawn Zou、Kenneth L. Brown

  DOI：10.1016/j.tetlet.2004.08.110

  日期：2004.10

  A variety of α-indole nucleosides are easily prepared from α-indoline nucleosides in excellent yield and at moderate temperature using manganese dioxide and molecular sieves in benzene or methylene chloride.

  使用二氧化锰和分子筛在苯或二氯甲烷中，由α-二氢吲哚核苷可轻松以优异的收率和适中的温度从α-二氢吲哚核苷制备各种α-吲哚核苷。
• Direct glycosylation: synthesis of α-indoline ribonucleosides
  作者：Tilak Chandra、Kenneth L. Brown

  DOI：10.1016/j.tetlet.2005.01.164

  日期：2005.3

  A selective synthesis of alpha-anomers of indoline nucleosides is described. Ribonucleosides of indoline, dimethylindoline and 5-bromoindoline are readily prepared in good yield by reacting indoline bases directly with the protected sugar, 2,3-O-(1-methylethylidene) 5-O-(triphenylmethyl)-D-ribofuranose in dry ethanol or methylene chloride in presence of molecular sieves at 40-60 degrees C. (C) 2005 Elsevier Ltd. All rights reserved.
• GLUCOKINASE ACTIVATORS
  申请人：NOVO NORDISK A/S

  公开号：EP1531815B1

  公开（公告）日：2014-09-24
• ANTIPROLIFERATIVE COMPOUNDS
  申请人：Boehringer Ingelheim International GmbH

  公开号：EP2350052B1

  公开（公告）日：2014-08-13
• COMPOUNDS TARGETING MUTANT CALRETICULIN
  申请人：MYELOPRO DIAGNOSTICS AND RESEARCH GmbH

  公开号：US20220024944A1

  公开（公告）日：2022-01-27

  The present invention relates to compounds binding to calreticulin which selectively inhibit growth of CALR mutant cells and/or exhibit selective cytotoxicity towards CALR mutant cells, to pharmaceutical compositions comprising such compounds as well as to their use in treating diseases or conditions caused by or associated with a mutation of CALR, in particular myeloid malignancies, such as myeloproliferative neoplasms or myelodysplasia syndrome. The present invention also relates to screening assays allowing the identification of such compounds.