di-tert-butyl ((2S,2'S)-((((sulfonylbis(prop-1-yne-3,1-diyl))bis(2,1-phenylene))bis(methylene))bis(azanediyl))bis(1-oxo-3-phenylpropane-1,2-diyl))dicarbamate | 1613038-89-3

• 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: di-tert-butyl ((2S,2'S)-((((sulfonylbis(prop-1-yne-3,1-diyl))bis(2,1-phenylene))bis(methylene))bis(azanediyl))bis(1-oxo-3-phenylpropane-1,2-diyl))dicarbamate
• CAS: 1613038-89-3
• 化学式: C₄₈H₅₄N₄O₈S
• 分子量: 847.045
• InChiKey: NZTDXSFFBIOPOH-COCZKOEFSA-N

物化性质

• 熔点：
  125-127 °C
• 沸点：
  1074.8±65.0 °C(predicted)
• 密度：
  1.26±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.01
• 重原子数：
  61.0
• 可旋转键数：
  14.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  169.0
• 氢给体数：
  4.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  di-tert-butyl ((2S,2'S)-((((sulfonylbis(prop-1-yne-3,1-diyl))bis(2,1-phenylene))bis(methylene))bis(azanediyl))bis(1-oxo-3-phenylpropane-1,2-diyl))dicarbamate 在 三乙胺 作用下， 以 氯仿 为溶剂， 以95%的产率得到
  参考文献：
  名称：

  Asymmetric Garratt–Braverman Cyclization: A Route to Axially Chiral Aryl Naphthalene–Amino Acid Hybrids

  摘要：

  We report the first example of a highly diastereoselective Garratt-Braverman cyclization leading to the synthesis of chiral aryl naphthalene amino acid hybrids in excellent yields. The stereogenecity in the amino acid has induced high diastereoselectivity for the reaction. Computations based on density functional theory indicated a lower activation free energy barrier for the M isomer as compared to that for the P diastereomer (Delta G = 3.48 kcal/mol). Comparison of the recorded CD spectrum of the product with the calculated one also supported the preferential formation of the M diastereomer.

  DOI：

  10.1021/jo500771g
• 作为产物：
  描述：

  2-碘苄胺 在 sodium sulfide 、 copper(l) iodide 、 trans-bis(triphenylphosphine)palladium dichloride 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三乙胺 、 间氯过氧苯甲酸 、 lithium bromide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 12.5h， 生成 di-tert-butyl ((2S,2'S)-((((sulfonylbis(prop-1-yne-3,1-diyl))bis(2,1-phenylene))bis(methylene))bis(azanediyl))bis(1-oxo-3-phenylpropane-1,2-diyl))dicarbamate
  参考文献：
  名称：

  Asymmetric Garratt–Braverman Cyclization: A Route to Axially Chiral Aryl Naphthalene–Amino Acid Hybrids

  摘要：

  We report the first example of a highly diastereoselective Garratt-Braverman cyclization leading to the synthesis of chiral aryl naphthalene amino acid hybrids in excellent yields. The stereogenecity in the amino acid has induced high diastereoselectivity for the reaction. Computations based on density functional theory indicated a lower activation free energy barrier for the M isomer as compared to that for the P diastereomer (Delta G = 3.48 kcal/mol). Comparison of the recorded CD spectrum of the product with the calculated one also supported the preferential formation of the M diastereomer.

  DOI：

  10.1021/jo500771g