[4-[tert-butyl(dimethyl)silyl]-3-oxobutan-2-yl] (2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoate | 1005350-44-6

• 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: [4-[tert-butyl(dimethyl)silyl]-3-oxobutan-2-yl] (2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoate
• CAS: 1005350-44-6
• 化学式: C₂₄H₃₉NO₅Si
• 分子量: 449.663
• InChiKey: GBAJORLDWOQWMN-NNBQYGFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.13
• 重原子数：
  31
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  81.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [4-[tert-butyl(dimethyl)silyl]-3-oxobutan-2-yl] (2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoate 在 四丁基氟化铵 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以82%的产率得到(2S)-2-tert-butoxycarbonylamino-3-phenylpropionic acid 1-methyl-2-oxopropyl ester
  参考文献：
  名称：

  Au(I)-catalyzed efficient synthesis of α-acyloxy-α′-silyl ketones from α-acyloxy-α-alkynylsilanes

  摘要：

  The Au(I)-catalyzed novel conversion of alpha-acyloxy-alpha-alkynylsilanes to alpha-acyloxy-alpha '-silyl ketones is reported. Ph3PAuOTf in dioxane in the presence of 1 equiv of H2O efficiently catalyzed both the [3,3] sigmatropic rearrangement and allenic transformation of the resulting ester to give the alpha-acyloxy-alpha '-silyl ketones in a one-pot procedure. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.11.023
• 作为产物：
  描述：

  在 三苯基膦氯金 、 水 、 silver trifluoromethanesulfonate 作用下， 以 1,4-二氧六环 为溶剂， 反应 7.0h， 以74%的产率得到[4-[tert-butyl(dimethyl)silyl]-3-oxobutan-2-yl] (2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoate
  参考文献：
  名称：

  Au(I)-catalyzed efficient synthesis of α-acyloxy-α′-silyl ketones from α-acyloxy-α-alkynylsilanes

  摘要：

  The Au(I)-catalyzed novel conversion of alpha-acyloxy-alpha-alkynylsilanes to alpha-acyloxy-alpha '-silyl ketones is reported. Ph3PAuOTf in dioxane in the presence of 1 equiv of H2O efficiently catalyzed both the [3,3] sigmatropic rearrangement and allenic transformation of the resulting ester to give the alpha-acyloxy-alpha '-silyl ketones in a one-pot procedure. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.11.023

文献信息

• Au(I)-catalyzed efficient synthesis of α-acyloxy-α′-silyl ketones from α-acyloxy-α-alkynylsilanes
  作者：Kazuhiko Sakaguchi、Takuya Okada、Tetsuro Shinada、Yasufumi Ohfune

  DOI：10.1016/j.tetlet.2007.11.023

  日期：2008.1

  The Au(I)-catalyzed novel conversion of alpha-acyloxy-alpha-alkynylsilanes to alpha-acyloxy-alpha '-silyl ketones is reported. Ph3PAuOTf in dioxane in the presence of 1 equiv of H2O efficiently catalyzed both the [3,3] sigmatropic rearrangement and allenic transformation of the resulting ester to give the alpha-acyloxy-alpha '-silyl ketones in a one-pot procedure. (C) 2007 Elsevier Ltd. All rights reserved.