(R)-2-(4-hydroxy-1-(3-methoxyphenyl)-butan-2-yl)isoindoline-1,3-dione | 1619261-42-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: (R)-2-(4-hydroxy-1-(3-methoxyphenyl)-butan-2-yl)isoindoline-1,3-dione
• 英文别名: 2-[(2R)-4-hydroxy-1-(3-methoxyphenyl)butan-2-yl]isoindole-1,3-dione
• CAS: 1619261-42-5
• 化学式: C₁₉H₁₉NO₄
• 分子量: 325.364
• InChiKey: VZXORIUDDSPLQN-AWEZNQCLSA-N

物化性质

• 沸点：
  522.7±50.0 °C(Predicted)
• 密度：
  1.283±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-2-(4-hydroxy-1-(3-methoxyphenyl)-butan-2-yl)isoindoline-1,3-dione 在 三氟甲磺酸 作用下， 以 二氯甲烷 为溶剂， 以70%的产率得到C₁₉H₁₇NO₃
  参考文献：
  名称：

  Synthesis of (S)-2-amino-7-methoxytetralin and isoindolo[1,2-a]isoquinolinone derivatives from l-aspartic acid

  摘要：

  This paper describes a new total synthesis for (S)-2-amino-7-methoxytetralin, (S)-7-MeO-AT, from L-aspartic acid in an overall yield of 10% over nine steps. The major loss was ascribed to a key intramolecular Friedel-Crafts cyclization step, which afforded up to 36% yield. Attempts to perform a Friedel-Crafts cyclization of an intermediate phthalimide protected amino alcohol 13 did not give the desired protected (S)-7-MeO-AT. On the other hand, two new isoindolo[1,2-alpha]isoquinolinone derivatives 14 and 15, were isolated in 21 and 11% yield, respectively. The yield of 15 was improved to 70%. (C) 2014 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2014.06.008
• 作为产物：
  描述：

  (R)-4-(3-methoxybenzyl)-1,3-oxazinan-2-one 在 三乙胺 、 lithium hydroxide 作用下， 以 甲醇 、 水 、 甲苯 为溶剂， 反应 20.0h， 生成 (R)-2-(4-hydroxy-1-(3-methoxyphenyl)-butan-2-yl)isoindoline-1,3-dione
  参考文献：
  名称：

  Synthesis of (S)-2-amino-7-methoxytetralin and isoindolo[1,2-a]isoquinolinone derivatives from l-aspartic acid

  摘要：

  This paper describes a new total synthesis for (S)-2-amino-7-methoxytetralin, (S)-7-MeO-AT, from L-aspartic acid in an overall yield of 10% over nine steps. The major loss was ascribed to a key intramolecular Friedel-Crafts cyclization step, which afforded up to 36% yield. Attempts to perform a Friedel-Crafts cyclization of an intermediate phthalimide protected amino alcohol 13 did not give the desired protected (S)-7-MeO-AT. On the other hand, two new isoindolo[1,2-alpha]isoquinolinone derivatives 14 and 15, were isolated in 21 and 11% yield, respectively. The yield of 15 was improved to 70%. (C) 2014 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2014.06.008

文献信息

• Synthesis of (S)-2-amino-7-methoxytetralin and isoindolo[1,2-a]isoquinolinone derivatives from l-aspartic acid
  作者：Jon Erik Aaseng、Odd R. Gautun

  DOI：10.1016/j.tet.2014.06.008

  日期：2014.8

  This paper describes a new total synthesis for (S)-2-amino-7-methoxytetralin, (S)-7-MeO-AT, from L-aspartic acid in an overall yield of 10% over nine steps. The major loss was ascribed to a key intramolecular Friedel-Crafts cyclization step, which afforded up to 36% yield. Attempts to perform a Friedel-Crafts cyclization of an intermediate phthalimide protected amino alcohol 13 did not give the desired protected (S)-7-MeO-AT. On the other hand, two new isoindolo[1,2-alpha]isoquinolinone derivatives 14 and 15, were isolated in 21 and 11% yield, respectively. The yield of 15 was improved to 70%. (C) 2014 Published by Elsevier Ltd.