1-(2-methylbut-3-yn-2-yl)indoline | 377073-07-9

• 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: 1-(2-methylbut-3-yn-2-yl)indoline
• 英文别名: 1-(1,1-dimethyl-2-propynyl)-2,3-dihydro-1H-indole；N-(1,1-dimethylpropargyl)indoline；1-(2-methylbut-3-yn-2-yl)-2,3-dihydroindole
• CAS: 377073-07-9
• 化学式: C₁₃H₁₅N
• 分子量: 185.269
• InChiKey: ABVVGQKJGMOYKU-UHFFFAOYSA-N

物化性质

• 沸点：
  284.0±23.0 °C(Predicted)
• 密度：
  1.051±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(2-methylbut-3-yn-2-yl)indoline 在 Lindlar's catalyst 、 K2 manganese(IV) oxide 、 N-溴代丁二酰亚胺(NBS) 、 hydroquinindine-2,5-diphenyl-4,6-pyrimidinediyl diether 、 氢气 、 叔丁基锂 、 potassium carbonate 、 potassium hexacyanoferrate(III) 作用下， 以 四氢呋喃 、 甲醇 、 水 、 N,N-二甲基甲酰胺 、 甲苯 、 叔丁醇 为溶剂， 反应 24.0h， 生成 1H-indole-3-carboxylic acid, 1-(2,3-dihydroxy-1,1-dimethylpropyl) methyl ester
  参考文献：
  名称：

  N-反向烯丙基化吲哚的合成研究。有效合成抗真菌吲哚生物碱和N-反向烯丙基色氨酸

  摘要：

  通过二氢吲哚的N-炔丙基化，末端炔烃的部分加氢以及使用化学二氧化锰的氧化为吲哚，开发了一种合成N -1,1-二甲基-2-丙烯基（反戊烯基）吲哚的有效方法。（CMD）。用于抗真菌吲哚生物碱的合成这种方法2，3，和Ñ -reverse异戊二烯化色氨酸。

  DOI：

  10.1016/s0040-4039(01)01492-7
• 作为产物：
  描述：

  吲哚啉 、 3-溴-3-甲基-1-丁炔 在 N,N-二异丙基乙胺 、 copper(l) chloride 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以65%的产率得到1-(2-methylbut-3-yn-2-yl)indoline
  参考文献：
  名称：

  （+）-okaramine J的全合成，具有非常容易的N-反向异戊烯基至C-异戊烯基aza-Claisen重排的功能。

  摘要：

  [反应：见正文]从1-色氨酸叔丁酯以12步的最长线性顺序实现了（+）-冈胺J的聚合全合成。一个关键的反应是将N-反向异戊酸酯化的六氢[2,3-b]吡咯并吲哚酸催化的室温氮杂-克莱森重排成C-异戊烯化的衍生物。

  DOI：

  10.1021/ol034822n

文献信息

• A General Synthesis of<i>N</i>-Reverse-Prenyl Indoles
  作者：Takayuki Shioiri、Fumiaki Yokokawa、Hideyuki Sugiyama、Toyohiko Aoyama

  DOI：10.1055/s-2004-822390

  日期：——

  A general method for the construction of N-reverse-prenyl indoles was established using copper catalyzed N-propargyl­ation, the Lindlar hydrogenation of the acetylenic bond, and dehydrogenation with chemical manganese dioxide as key steps. The antifungal indole alkaloids (1 and 2) and N-reverse-prenyl tryptophan (3) were efficiently synthesized by this method.

  利用铜催化的N-炔丙基化反应、Lindlar氢化反应以及化学二氧化锰脱氢反应作为关键步骤，建立了一种构建N-反式异戊二烯基吲哚类化合物的通用方法。该方法成功高效地合成了抗真菌吲哚生物碱（1和2）以及N-反式异戊二烯基色氨酸（3）。
• Aldehyde dehydrogenase inhibitors: α,β-Acetylenic N-substituted aminothiolesters are reversible growth inhibitors of normal epithelial but irreversible apoptogens for cancer epithelial cells from human prostate in culture
  作者：Gerard Quash、Guy Fournet、Charlotte Courvoisier、Rosa M. Martinez、Jacqueline Chantepie、Marie Julie Paret、Julie Pharaboz、Marie Odile Joly-Pharaboz、Jacques Goré、Jean André

  DOI：10.1016/j.ejmech.2007.06.004

  日期：2008.5

  The pharmacomodulation of the N atom of alpha,beta-acetylenic aminothiolesters or the replacement of the thiolester moiety by more electroplfflic groups did not permit any clear rationale to be established for improving the selective growth-inhibitory activity of this family of compounds over that of the previously synthesized alpha,beta-acetylenic aminothiolesters DIMATE and MATE [G. Quash, G. Fournet, J. Chantepie, J. Gore, C. Ardiet, D. Ardail, Y. Michal, U. Reichert, Biochem Phannacol 64 (2002) 1279-92]. Hence DIMATE and MATE were investigated more thoroughly for selectivity and growth-inhibitory activity using human prostate epithelial normal cells (HPENC) on the one hand and human prostate epithelial cancer cells (DU145) on the other. Unequivocal evidence was obtained showing that both compounds were reversible growth inhibitors of HPENC but irreversible growth inhibitors of DU145. Growth-inhibition of DU145 was due to the induction of early apoptosis as revealed by the flow cytometric analytical profile of inhibitor-treated cells, of the decrease in the redox potential and increase in superoxide anion content of their mitochondria. Of the two intracellular enzymes: aldehyde dehydrogenases 1 and 3 (ALDH1 and ALDH3) targeted by DIMATE and MATE, ALDH3 was inhibited to the same extent by both compounds whereas ALDH1 was less susceptible to inhibition by MATE. As the induction of ALDH3 by xenobiotics is hormone-dependent, MATE, the more selective of the two inhibitors, is a useful tool not only for examining the role of the ALDH3 isoform in hormone-sensitive and resistant prostate cancer cells in culture but also for investigating if it can inhibit the growth of xenografts of prostate cancer in immunodeficient mice. (C) 2007 Elsevier Masson SAS. All rights reserved.
• A stereoselective synthetic approach to (2S,3R)-N-(1′,1′-dimethyl-2′,3′-epoxypropyl)-3-hydroxytryptophan, a component of cyclomarin A
  作者：Darren B. Hansen、Alan S. Lewis、Steven J. Gavalas、Madeleine M. Joullié

  DOI：10.1016/j.tetasy.2005.10.040

  日期：2006.1

  A stereoselective synthetic approach to (2S,3R)-N-(1',1'-dimethyl-2',3'-epoxypropyl)-3-hydroxytryptophan an amino acid contained in cyclomarin A was accomplished. The synthesis is based on a diastereoselective addition of an indole Grignard into a chiral serine aldehyde equivalent. (c) 2005 Elsevier Ltd. All rights reserved.
• Practical Synthesis of 7-Prenylindole
  作者：Xin Xiong、Michael C. Pirrung

  DOI：10.1021/jo070734v

  日期：2007.7.1

  7-Prenylindole is a useful building block for natural product and natural product analogue synthesis. While there have been several past syntheses of 7-prenylindole, none of them is very practical for its preparation on scale. Using an aza-Claisen rearrangement as the key step, 7-prenylindole has been prepared in four steps from indoline in 62% overall yield.