N-(2,2-dimethoxyethyl)-α-(3,4-dimethoxyphenyl)glycine | 1370371-82-6

• 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: N-(2,2-dimethoxyethyl)-α-(3,4-dimethoxyphenyl)glycine
• 英文别名: (+)-N-2,2-dimethoxyethyl-2-(3,4-dimethoxyphenyl)glycine；2-(2,2-Dimethoxyethylamino)-2-(3,4-dimethoxyphenyl)acetic acid；2-(2,2-dimethoxyethylamino)-2-(3,4-dimethoxyphenyl)acetic acid
• CAS: 1370371-82-6
• 化学式: C₁₄H₂₁NO₆
• 分子量: 299.324
• InChiKey: ICZVPPKSAHIKIN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  21
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  86.2
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-(2,2-dimethoxyethyl)-α-(3,4-dimethoxyphenyl)glycine 在 盐酸 、 硼烷四氢呋喃络合物 、 5%-palladium/activated carbon 、 氢气 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 24.0h， 生成 (6,7-二甲氧基-1,2,3,4-四氢-异喹啉-1-基)-甲醇
  参考文献：
  名称：

  A concise synthesis of tetrahydroisoquinoline-1-carboxylic acids using a Petasis reaction and Pomeranz–Fritsch–Bobbitt cyclization sequence

  摘要：

  A sequence of two reactions: the Petasis reaction, in which an aminoacetaldehyde acetal was used as the amine component, followed by Pomeranz-Fritsch-Bobbitt cyclization, has been shown to be a convenient and simple method for the synthesis of tetrahydroisoquinoline-1-carboxylic acids. Using this method several acids have been prepared in good to excellent yields and characterized as hydrochloride salts. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.02.005
• 作为产物：
  描述：

  N-(2,2-dimethoxyethyl)-N-benzyl-α-(3,4-dimethoxyphenyl)glycine 在 氢气 、 palladium(II) hydroxide 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以97%的产率得到N-(2,2-dimethoxyethyl)-α-(3,4-dimethoxyphenyl)glycine
  参考文献：
  名称：

  A concise synthesis of tetrahydroisoquinoline-1-carboxylic acids using a Petasis reaction and Pomeranz–Fritsch–Bobbitt cyclization sequence

  摘要：

  A sequence of two reactions: the Petasis reaction, in which an aminoacetaldehyde acetal was used as the amine component, followed by Pomeranz-Fritsch-Bobbitt cyclization, has been shown to be a convenient and simple method for the synthesis of tetrahydroisoquinoline-1-carboxylic acids. Using this method several acids have been prepared in good to excellent yields and characterized as hydrochloride salts. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.02.005

文献信息

• Synthesis of (+)-6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline-1-carboxylic Acid, a Diastereoselective Approach
  作者：Ilona Bułyszko、Maria Chrzanowska、Agnieszka Grajewska、Maria D. Rozwadowska

  DOI：10.1002/ejoc.201403218

  日期：2015.1

  The diastereoselective synthesis of (+)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid (90 % ee) was accomplished by employing a combination of two synthetic methods, that is, the Petasis synthesis of amino acids and the Pomeranz–Fritsch–Bobbitt synthesis of tetrahydroisoquinoline derivatives. The stereochemical outcome of the synthesis was controlled by chiral aminoacetaldehyde acetals

  (+)-6,7-二甲氧基-1,2,3,4-四氢异喹啉-1-羧酸(90%ee)的非对映选择性合成是通过两种合成方法的组合完成的，即Petasis合成氨基酸和四氢异喹啉衍生物的 Pomeranz-Fritsch-Bobbitt 合成。合成的立体化学结果由手性氨基乙醛缩醛控制，手性氨基乙醛缩醛用作 Petasis 步骤的胺组分，以在一个简单的操作中产生用于四氢异喹啉环形成的 Pomeranz-Fritsch-Bobbitt 底物。
• A concise synthesis of tetrahydroisoquinoline-1-carboxylic acids using a Petasis reaction and Pomeranz–Fritsch–Bobbitt cyclization sequence
  作者：Maria Chrzanowska、Agnieszka Grajewska、Zofia Meissner、Maria Rozwadowska、Iwona Wiatrowska

  DOI：10.1016/j.tet.2012.02.005

  日期：2012.4

  A sequence of two reactions: the Petasis reaction, in which an aminoacetaldehyde acetal was used as the amine component, followed by Pomeranz-Fritsch-Bobbitt cyclization, has been shown to be a convenient and simple method for the synthesis of tetrahydroisoquinoline-1-carboxylic acids. Using this method several acids have been prepared in good to excellent yields and characterized as hydrochloride salts. (C) 2012 Elsevier Ltd. All rights reserved.