naphthalen-1-ylmethyl (2S)-3-(1H-indol-3-yl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate | 1394172-70-3

• 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: naphthalen-1-ylmethyl (2S)-3-(1H-indol-3-yl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate
• CAS: 1394172-70-3
• 化学式: C₂₇H₂₈N₂O₄
• 分子量: 444.53
• InChiKey: BOPGHNDDBMSQEF-DEOSSOPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  80.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  naphthalen-1-ylmethyl (2S)-3-(1H-indol-3-yl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate 在 盐酸 作用下， 以 乙酸乙酯 为溶剂， 以89%的产率得到naphthalen-1-ylmethyl (2S)-2-amino-3-(1H-indol-3-yl)propanoate;hydrochloride
  参考文献：
  名称：

  Regioselective Diversification of a Cardiac Glycoside, Lanatoside C, by Organocatalysis

  摘要：

  Acylation of lanatoside C in the presence of organocatalyst 5 gave the C(4'''')-O-acylate in up to 90% regioselectivity (catalyst-controlled regioselectivity). Various functionalized acyl groups can be introduced at the C(4'''')-OH by a mixed anhydride method in the presence of 5 or the related organocatalyst. On the other hand, DMAP-catalyzed acylation of lanatoside C gave the C(3'''')-O-acylate in up to 97% regioselectivity (substrate-controlled regioselectivity). Thus, diverse regioselective introduction of acyl groups among eight free hydroxy groups of lanatoside C was achieved.

  DOI：

  10.1021/jo301007x
• 作为产物：
  描述：

  1-萘甲醇 、 N-叔丁氧羰基-L-色氨酸 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以99%的产率得到naphthalen-1-ylmethyl (2S)-3-(1H-indol-3-yl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate
  参考文献：
  名称：

  Regioselective Diversification of a Cardiac Glycoside, Lanatoside C, by Organocatalysis

  摘要：

  Acylation of lanatoside C in the presence of organocatalyst 5 gave the C(4'''')-O-acylate in up to 90% regioselectivity (catalyst-controlled regioselectivity). Various functionalized acyl groups can be introduced at the C(4'''')-OH by a mixed anhydride method in the presence of 5 or the related organocatalyst. On the other hand, DMAP-catalyzed acylation of lanatoside C gave the C(3'''')-O-acylate in up to 97% regioselectivity (substrate-controlled regioselectivity). Thus, diverse regioselective introduction of acyl groups among eight free hydroxy groups of lanatoside C was achieved.

  DOI：

  10.1021/jo301007x

文献信息

• Regioselective Diversification of a Cardiac Glycoside, Lanatoside C, by Organocatalysis
  作者：Yoshihiro Ueda、Kenji Mishiro、Keisuke Yoshida、Takumi Furuta、Takeo Kawabata

  DOI：10.1021/jo301007x

  日期：2012.9.21

  Acylation of lanatoside C in the presence of organocatalyst 5 gave the C(4'''')-O-acylate in up to 90% regioselectivity (catalyst-controlled regioselectivity). Various functionalized acyl groups can be introduced at the C(4'''')-OH by a mixed anhydride method in the presence of 5 or the related organocatalyst. On the other hand, DMAP-catalyzed acylation of lanatoside C gave the C(3'''')-O-acylate in up to 97% regioselectivity (substrate-controlled regioselectivity). Thus, diverse regioselective introduction of acyl groups among eight free hydroxy groups of lanatoside C was achieved.