(R)-3-butanamidobutanoic acid tert-butyl ester | 1067647-39-5

• 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: (R)-3-butanamidobutanoic acid tert-butyl ester
• 英文别名: tert-butyl (3R)-3-(butanoylamino)butanoate
• CAS: 1067647-39-5
• 化学式: C₁₂H₂₃NO₃
• 分子量: 229.32
• InChiKey: XFTNKHLKSJYEOX-SECBINFHSA-N

物化性质

• 沸点：
  360.2±25.0 °C(Predicted)
• 密度：
  0.969±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-3-butanamidobutanoic acid tert-butyl ester 在 盐酸 作用下， 反应 16.0h， 生成 (R)-3-氨基丁酸
  参考文献：
  名称：

  Burkholderia cepacia lipase and activated β-lactams in β-dipeptide and β-amino amide synthesis

  摘要：

  The work describes fluorine-activated and N-Boc-activated beta-lactams as acyl donors to N-nucleophiles in the presence of Burkholderia cepacia lipase (lipase PS-D). Fluorine activation at the beta-lactam ring causes the ring to open in high enantioselectivity and allows the preparation of beta-dipeptides and beta-amino amides. in the case of N-Boc-activation, the chemical ring opening is significant. beta-Dipeptide formation can then be considerably enhanced by the presence of lipase PS-D and/or by temperature. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.07.017
• 作为产物：
  描述：

  醋酸叔丁酯 在 高氯酸 、 lipase A from candida antarctica 作用下， 反应 29.0h， 生成 (R)-3-butanamidobutanoic acid tert-butyl ester 、 (S)-3-butanamidobutanoic acid tert-butyl ester 、 (S)-3-aminobutanoic acid tert-butyl ester butanoate salt
  参考文献：
  名称：

  β-氨基酯的酰化和β-氨基酯的水解：南极假丝酵母脂肪酶A作为化学选择性脱保护催化剂

  摘要：

  将南极假丝酵母（CAL-A）中的脂肪酶A在丁酸乙酯中进行N-酰化反应用于动力学拆分3-氨基-3-苯基丙酸（E > 100），3-氨基-4-甲基戊酸的叔丁基酯酸（E > 100）和3-氨基丁酸（E = 60），范围为1.0-2.0  m。然后，使用N-酰化的拆分产品，研究了CAL-A水解酰胺和大体积叔丁酯的出色能力。在所有的N-酰化的叔丁基酯中，化学选择性有利于酰胺键的裂解。该叔叔丁基酯键与3-氨基-3-苯基丙酸酯保持完整，而3-氨基-4-甲基戊酸酯和3-氨基丁酸酯则由CAL-A催化叔丁酯水解，然后再进行酰胺水解。

  DOI：

  10.1002/cctc.201501381

文献信息

• METHOD FOR ENZYMATIC PREPARATION OF R-3-AMINOBUTYRIC ACID
  申请人：Abiochem Biotechnology Co., Ltd.

  公开号：EP3680340A1

  公开（公告）日：2020-07-15

  An R-3-aminobutyric acid preparation method with high efficiency and high stereoselectivity. The method comprises using aspartase with stereoisomerization catalytic activity derived from Escherichia coli to efficiently convert butenoic acid into R-3-aminobutyric acid. After only 24 h of reaction, the conversion rate is as high as ≥98%, and the ee value is ≥ 99.9%. The conversion efficiency is greatly improved, the reaction time is shortened, and the production costs are reduced. The method features a high yield, a high conversion rate, low costs, a short production cycle, a simple process, ease of enlargement, suitability for mass production and the like.

  一种具有高效率和高立体选择性的 R-3-氨基丁酸制备方法。该方法包括利用来自大肠杆菌的具有立体异构催化活性的天冬氨酸酶将丁烯酸高效转化为 R-3-氨基丁酸。仅经过 24 小时的反应，转化率就高达≥98%，ee 值≥99.9%。大大提高了转化效率，缩短了反应时间，降低了生产成本。该方法具有收率高、转化率高、成本低、生产周期短、工艺简单、易于放大、适合大规模生产等特点。
• Method for enzymatic preparation of R-3 aminobutyric acid
  申请人：ABIOCHEM BIOTECHNOLOGY CO., LTD.

  公开号：US11220701B2

  公开（公告）日：2022-01-11

  An R-3-aminobutyric acid preparation method with high efficiency and high stereoselectivity. The method comprises using aspartase with stereoisomerization catalytic activity derived from Escherichia coli to efficiently convert butenoic acid into R-3-aminobutyric acid. After only 24 h of reaction, the conversion rate is as high as ≥98%, and the ee value is ≥99.9%. The conversion efficiency is greatly improved, the reaction time is shortened, and the production costs are reduced. The method features a high yield, a high conversion rate, low costs, a short production cycle, a simple process, ease of enlargement, suitability for mass production and the like.

  一种具有高效率和高立体选择性的 R-3-氨基丁酸制备方法。该方法包括利用来自大肠杆菌的具有立体异构催化活性的天冬氨酸酶将丁烯酸高效转化为 R-3-氨基丁酸。仅经过 24 小时的反应，转化率就高达≥98%，ee 值≥99.9%。大大提高了转化效率，缩短了反应时间，降低了生产成本。该方法具有收率高、转化率高、成本低、生产周期短、工艺简单、易于放大、适合大规模生产等特点。
• METHOD FOR ENZYMATIC PREPARATION OF R-3 AMINOBUTYRIC ACID
  申请人：ABIOCHEM BIOTECHNOLOGY CO., LTD.

  公开号：US20200232002A1

  公开（公告）日：2020-07-23

  An R-3-aminobutyric acid preparation method with high efficiency and high stereoselectivity. The method comprises using aspartase with stereoisomerization catalytic activity derived from Escherichia coli to efficiently convert butenoic acid into R-3-aminobutyric acid. After only 24 h of reaction, the conversion rate is as high as ≥98%, and the ee value is ≥99.9%. The conversion efficiency is greatly improved, the reaction time is shortened, and the production costs are reduced. The method features a high yield, a high conversion rate, low costs, a short production cycle, a simple process, ease of enlargement, suitability for mass production and the like.