methyl 2-hydroxy-3-methyl-3-(1-methylindol-3-yl)butanoate | 406500-70-7

• 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: methyl 2-hydroxy-3-methyl-3-(1-methylindol-3-yl)butanoate
• CAS: 406500-70-7
• 化学式: C₁₅H₁₉NO₃
• 分子量: 261.321
• InChiKey: SMLOIKPNIFOCAP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  51.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 2-hydroxy-3-methyl-3-(1-methylindol-3-yl)butanoate 在 吡啶 二苯基磷酸 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 以85%的产率得到2-Azido-3-methyl-3-(1-methyl-1H-indol-3-yl)-butyric acid methyl ester
  参考文献：
  名称：

  Asymmetric Synthesis of the Highly Methylated Tryptophan Portion of the Hemiasterlin Tripeptides

  摘要：

  [GRAPHICS]The asymmetric synthesis of the methylated tryptophan portion of hemiasterlin peptides is described. The key reactions are a SnCl4-mediated ring opening of epoxynitriles or epoxysulfones by N-methylindole followed by an asymmetric Strecker reaction. A second approach involving opening of glycidic esters by indoles is also described.

  DOI：

  10.1021/ol016982+
• 作为产物：
  描述：

  1-甲基吲哚 、 3,3-二甲基-环氧乙烷羧酸甲酯 在 四氯化锡 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以70%的产率得到methyl 2-hydroxy-3-methyl-3-(1-methylindol-3-yl)butanoate
  参考文献：
  名称：

  Asymmetric Synthesis of the Highly Methylated Tryptophan Portion of the Hemiasterlin Tripeptides

  摘要：

  [GRAPHICS]The asymmetric synthesis of the methylated tryptophan portion of hemiasterlin peptides is described. The key reactions are a SnCl4-mediated ring opening of epoxynitriles or epoxysulfones by N-methylindole followed by an asymmetric Strecker reaction. A second approach involving opening of glycidic esters by indoles is also described.

  DOI：

  10.1021/ol016982+

文献信息

• Asymmetric Synthesis of the Highly Methylated Tryptophan Portion of the Hemiasterlin Tripeptides
  作者：Ranga Reddy、James B. Jaquith、Venugopal Rao Neelagiri、Sherine Saleh-Hanna、Tony Durst

  DOI：10.1021/ol016982+

  日期：2002.3.1

  [GRAPHICS]The asymmetric synthesis of the methylated tryptophan portion of hemiasterlin peptides is described. The key reactions are a SnCl4-mediated ring opening of epoxynitriles or epoxysulfones by N-methylindole followed by an asymmetric Strecker reaction. A second approach involving opening of glycidic esters by indoles is also described.