(R)-2-amino-3-(1-(tert-butoxycarbonyl)-1H-indol-3-yl)-2-methylpropanoic acid | 220155-71-5

• 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: (R)-2-amino-3-(1-(tert-butoxycarbonyl)-1H-indol-3-yl)-2-methylpropanoic acid
• 英文别名: (2R)-2-amino-2-methyl-3-[1-[(2-methylpropan-2-yl)oxycarbonyl]indol-3-yl]propanoic acid
• CAS: 220155-71-5
• 化学式: C₁₇H₂₂N₂O₄
• 分子量: 318.373
• InChiKey: OWGGGNGCGLPYNA-QGZVFWFLSA-N

物化性质

• 沸点：
  481.1±55.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  94.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (R)-2-amino-3-(1-(tert-butoxycarbonyl)-1H-indol-3-yl)-2-methylpropanoic acid 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 生成 alpha-甲基-D-色氨酸
  参考文献：
  名称：

  The stereocontrolled synthesis of orthogonally protected (R)-α-methyltryptophan

  摘要：

  An expedient and highly stereocontrolled route to (R)-alpha-methyltryptophan and its orthogonally protected analogs has been developed via a four-step conversion from L-alanine in good overall yields. The stereochemistry of the products is confirmed by X-ray diffraction analysis, NMR spectroscopy and optical rotations. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)02302-8
• 作为产物：
  描述：

  tert-butyl 3-[[(3R,10bR)-3-methyl-2,5-dioxo-10bH-[1,3]oxazolo[3,2-c][1,3]benzoxazin-3-yl]methyl]indole-1-carboxylate 在 lithium hydroxide 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 0.33h， 以82%的产率得到(R)-2-amino-3-(1-(tert-butoxycarbonyl)-1H-indol-3-yl)-2-methylpropanoic acid
  参考文献：
  名称：

  The stereocontrolled synthesis of orthogonally protected (R)-α-methyltryptophan

  摘要：

  An expedient and highly stereocontrolled route to (R)-alpha-methyltryptophan and its orthogonally protected analogs has been developed via a four-step conversion from L-alanine in good overall yields. The stereochemistry of the products is confirmed by X-ray diffraction analysis, NMR spectroscopy and optical rotations. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)02302-8

文献信息

• The stereocontrolled synthesis of orthogonally protected (R)-α-methyltryptophan
  作者：Murray Goodman、Jinfang Zhang、Peter Gantzel、Ettore Benedetti

  DOI：10.1016/s0040-4039(98)02302-8

  日期：1998.12

  An expedient and highly stereocontrolled route to (R)-alpha-methyltryptophan and its orthogonally protected analogs has been developed via a four-step conversion from L-alanine in good overall yields. The stereochemistry of the products is confirmed by X-ray diffraction analysis, NMR spectroscopy and optical rotations. (C) 1998 Elsevier Science Ltd. All rights reserved.