4-azido-2-bromo-3,3-dimethoxybutanoic acid | 845523-90-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 4-azido-2-bromo-3,3-dimethoxybutanoic acid
• 英文别名: 4-Azido-2-bromo-3,3-dimethoxybutanoic acid
• CAS: 845523-90-2
• 化学式: C₆H₁₀BrN₃O₄
• 分子量: 268.067
• InChiKey: VUVUCVZQWLETHI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  70.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-azido-2-bromo-3,3-dimethoxybutanoic acid 在 sodium hydroxide 、 三乙胺 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 21.0h， 生成 N-(Carboxymethyl)glycin-methylester
  参考文献：
  名称：

  Synthesis of new 3,3-dimethoxyazetidine-2-carboxylic acid derivatives

  摘要：

  Cyclization of gamma-amino-alpha-bromocarboxylic esters resulted in an efficient synthesis of new 3,3-dimethoxyazetidine-2-carboxylates, that is, methyl N-t-butyl-3,3-dimethoxyazetidine-2-carboxylic ester and 3,3-dimethoxyazetidine-2-carboxylic acid, or 3-bromo-4,4-dimethoxypyrrolidin-2-ones, depending on the substituent at nitrogen. Reduction of the 3,3-dimethoxyazetidine-2-carboxylates gave the corresponding 3,3-dimethoxy-2-(hydroxymethyl)azetidines. These novel cyclic amino acid derivatives. available-on multigram scale, have a suitably protected carbonyl function at the 3-position, which enables further functionalization. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.10.125
• 作为产物：
  描述：

  (E)4-氯-3-甲氧基-2-丁稀酸甲酯 在 sodium hydroxide 、 N-溴代丁二酰亚胺(NBS) 、 sodium azide 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 8.0h， 生成 4-azido-2-bromo-3,3-dimethoxybutanoic acid
  参考文献：
  名称：

  Synthesis of new 3,3-dimethoxyazetidine-2-carboxylic acid derivatives

  摘要：

  Cyclization of gamma-amino-alpha-bromocarboxylic esters resulted in an efficient synthesis of new 3,3-dimethoxyazetidine-2-carboxylates, that is, methyl N-t-butyl-3,3-dimethoxyazetidine-2-carboxylic ester and 3,3-dimethoxyazetidine-2-carboxylic acid, or 3-bromo-4,4-dimethoxypyrrolidin-2-ones, depending on the substituent at nitrogen. Reduction of the 3,3-dimethoxyazetidine-2-carboxylates gave the corresponding 3,3-dimethoxy-2-(hydroxymethyl)azetidines. These novel cyclic amino acid derivatives. available-on multigram scale, have a suitably protected carbonyl function at the 3-position, which enables further functionalization. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.10.125

文献信息

• [EN] COMPOSITIONS AND METHODS FOR MODULAR CONTROL OF BIOORTHOGONAL LIGATION<br/>[FR] COMPOSITIONS ET PROCÉDÉS POUR LE CONTRÔLE MODULAIRE D'UNE LIGATURE BIO-ORTHOGONALE
  申请人：UNIV NEW YORK STATE RES FOUND

  公开号：WO2020113077A9

  公开（公告）日：2020-08-13
• COMPOSITIONS AND METHODS FOR MODULAR CONTROL OF BIOORTHOGONAL LIGATION
  申请人：LAUGHLIN Scott

  公开号：US20220218661A1

  公开（公告）日：2022-07-14

  The present invention provides a compound having the structure: wherein R 1 is H or a protecting group; R 2 and R 3 are each independently H, halo, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 alkyl-C(O)NHR 6 , C 1 -C 6 alkyl-C(O)OR 6 , wherein R 6 is H, C 1 -C 6 alkyl, C 2 -C 6 alkenyl or C 2 -C 6 alkynyl, or R 2 and R 3 combine to form a 3-7 membered cycloalkyl, heterocycloalkyl, aryl or heteroaryl ring; and R 4 and R 5 are each independently halo.
• Synthesis of new 3,3-dimethoxyazetidine-2-carboxylic acid derivatives
  作者：Sven Mangelinckx、Marc Boeykens、Maarten Vliegen、Johan Van der Eycken、Norbert De Kimpe

  DOI：10.1016/j.tetlet.2004.10.125

  日期：2005.1

  Cyclization of gamma-amino-alpha-bromocarboxylic esters resulted in an efficient synthesis of new 3,3-dimethoxyazetidine-2-carboxylates, that is, methyl N-t-butyl-3,3-dimethoxyazetidine-2-carboxylic ester and 3,3-dimethoxyazetidine-2-carboxylic acid, or 3-bromo-4,4-dimethoxypyrrolidin-2-ones, depending on the substituent at nitrogen. Reduction of the 3,3-dimethoxyazetidine-2-carboxylates gave the corresponding 3,3-dimethoxy-2-(hydroxymethyl)azetidines. These novel cyclic amino acid derivatives. available-on multigram scale, have a suitably protected carbonyl function at the 3-position, which enables further functionalization. (C) 2004 Elsevier Ltd. All rights reserved.