tert-butyl (R)-1-(methoxycarbonyl)-3-(1H-indol-3-yl)propylcarbamate | 1350542-08-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: tert-butyl (R)-1-(methoxycarbonyl)-3-(1H-indol-3-yl)propylcarbamate
• 英文别名: methyl (2R)-4-(1H-indol-3-yl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoate
• CAS: 1350542-08-3
• 化学式: C₁₈H₂₄N₂O₄
• 分子量: 332.4
• InChiKey: LKHYHFPPPFCLBG-OAHLLOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  80.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-[(三甲基甲硅烷基)乙炔基]苯胺 在 吡啶 、 三乙基硅烷 、 Jones reagent 、 palladium 10% on activated carbon 、 四丁基氟化铵 、 碘 、 palladium diacetate 、 potassium carbonate 、 氯化铵 、 对甲苯磺酸 、 magnesium 、 N,N-二异丙基乙胺 、 三苯基膦 、 copper(l) chloride 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 丙酮 、 乙腈 为溶剂， 反应 9.25h， 生成 tert-butyl (R)-1-(methoxycarbonyl)-3-(1H-indol-3-yl)propylcarbamate 、 tert-butyl (S)-1-(methoxycarbonyl)-3-(1H-indol-3-yl)propylcarbamate
  参考文献：
  名称：

  Synthesis of optically active homotryptophan and its oxygen and sulfur analogues

  摘要：

  D-Homotryptophan and its sulfur analogue have been synthesized by Sonogashira coupling between 3-iodoheteroarenes and ethynyloxazolidine followed by reduction of triple bond and oxidation of alcohol to acid. L-Homotryptophan and its oxygen analogue have been synthesized from silylated internal alkyne using Larock's heteroannulation as the key reaction. The allcynyloxazolidines were synthesized from L-serine and L-glutamic acid, respectively. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.10.055

文献信息

• Synthesis of optically active homotryptophan and its oxygen and sulfur analogues
  作者：Koushik Goswami、Sibasish Paul、Sandesh T. Bugde、Surajit Sinha

  DOI：10.1016/j.tet.2011.10.055

  日期：2012.1

  D-Homotryptophan and its sulfur analogue have been synthesized by Sonogashira coupling between 3-iodoheteroarenes and ethynyloxazolidine followed by reduction of triple bond and oxidation of alcohol to acid. L-Homotryptophan and its oxygen analogue have been synthesized from silylated internal alkyne using Larock's heteroannulation as the key reaction. The allcynyloxazolidines were synthesized from L-serine and L-glutamic acid, respectively. (C) 2011 Elsevier Ltd. All rights reserved.