N-lauroyl-β-aminopropionitrile | 164394-80-3

• 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: N-lauroyl-β-aminopropionitrile
• 英文别名: Dodecanamide, N-(2-cyanoethyl)-；N-(2-cyanoethyl)dodecanamide
• CAS: 164394-80-3
• 化学式: C₁₅H₂₈N₂O
• mdl: MFCD20928689
• 分子量: 252.4
• InChiKey: KKYWYBUZCZPDQE-UHFFFAOYSA-N

物化性质

• 沸点：
  437.4±28.0 °C(Predicted)
• 密度：
  0.916±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  18
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.866
• 拓扑面积：
  52.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-lauroyl-β-aminopropionitrile 在 氢氧化钾 作用下， 以 乙二醇甲醚 为溶剂， 反应 6.0h， 以85%的产率得到N-(十二酰基)-Β-丙氨酸
  参考文献：
  名称：

  有机介质中N-月桂酰-β-丙氨酸同系物的酶促合成

  摘要：

  AbstractEnyzmatic amidation of the primary amines β‐alanine ethyl ester and 3‐aminopropionitrile with methyl laurate by means of immobilized lipase (Candida antarctica lipase, CAL) resulted in the formation in good yield of N‐lauroyl‐β‐alanine ethyl ester and 3‐(N‐lauroylamino)‐propionitrile, respectively. When 3‐amino‐propionitrile was used as substrate, diisopropyl ether was a suitable solvent. Changing the reaction temperature (12–80°C) did not affect the yields, and room temperature was a suitable temperature for this reaction. In the investigation of reaction conditions, the use of equimolar amounts (5 mmol) of substrate and ester, along with 0.5 g of CAL, in diisopropyl ether gave the best yield (99.3%) after 24 h of incubation at 24°C. The enzyme activity in the amidation reaction did not decrease even after six uses. With β‐alanine ethyl ester hydrochloride as substrate, diisopropyl ether was unsuited as a solvent owing to the low solubility of the substrate in this solvent.In this reaction, the best yield (82.0%) was attained by using dioxane as solvent. CAL achieved higher extents of amide synthesis with long‐chain than with short‐chain ester substrates. The enzyme accepted only nonbulky primary amines as substrates.

  DOI：

  10.1007/s11746-997-0231-9
• 作为产物：
  描述：

  3-氨基丙腈 、 月桂酸甲酯 在 Candida antarctica lipase 作用下， 以 异丙醚 为溶剂， 以99%的产率得到N-lauroyl-β-aminopropionitrile
  参考文献：
  名称：

  Yang, Bo; Zhang, Yanjun; Zhang, Shusheng, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2005, vol. 44, # 6, p. 1312 - 1316

  摘要：

  DOI：

文献信息

• Processes for the preparation of N-(long-chain acyl)amino acid and salt
  申请人：Kao Corporation

  公开号：US05646317A1

  公开（公告）日：1997-07-08

  To provide processes suitable for industrial production by which high-purity N-(long-chain acyl)amino acid and salt thereof can be prepared from inexpensive raw materials. An alkyl ester of a fatty acid (2) is reacted with an aminonitrile (3) in the presence of a basic catalyst to form an amidonitrile (1), the amidonitrile (1) is hydrolyzed into an N-(long-chain acyl)amino acid salt (4) in the presence of a basic substance, the pH of the resulting aqueous solution is adjusted to a pH from 1 to 5 with a mineral acid to form an N-(long-chain acyl)amino acid (5), and this amino acid is recovered. ##STR1## wherein R.sup.1 CO-- represents a fatty acid residue having 8 to 22 carbon atoms; R.sup.2 represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms; R.sup.3 represents an alkylene group having 1 to 5 carbon atoms; R.sup.4 represents an alkyl group having 1 to 4 carbon atoms; and M represents a monovalent cation.

  提供适合工业生产的工艺，可以从廉价原料中制备高纯度的N-(长链酰基)氨基酸及其盐。脂肪酸的烷基酯（2）在碱性催化剂的存在下与氨基腈（3）反应，形成酰基腈（1），酰基腈（1）在碱性物质的存在下水解成N-(长链酰基)氨基酸盐（4），将产生的水溶液的pH值用矿酸调整到pH值为1至5，形成N-(长链酰基)氨基酸（5），然后回收这种氨基酸。其中R.sup.1 CO--代表具有8至22个碳原子的脂肪酸残基；R.sup.2代表氢原子或具有1至3个碳原子的烷基基团；R.sup.3代表具有1至5个碳原子的烷基基团；R.sup.4代表具有1至4个碳原子的烷基基团；M代表一价阳离子。
• Processes for the preparation of N-(long-chain acyl)amino acid and salt thereof, and intermediate amidonitrile and process for the preparation thereof
  申请人：Kao Corporation

  公开号：EP0649836A1

  公开（公告）日：1995-04-26

  To provide processes suitable for industrial production by which high-purity N-(long-chain acyl)amino acid and salt thereof can be prepared from inexpensive raw materials. An alkyl ester of a fatty acid (2) is reacted with an aminonitrile (3) in the presence of a basic catalyst to form an amidonitrile (1), the amidonitrile (1) is hydrolyzed into an N-(long-chain acyl)amino acid salt (4) in the presence of a basic substance, the pH of the resulting aqueous solution is adjusted to a pH from 1 to 5 with a mineral acid to form an N-(long-chain acyl)amino acid (5), and this amino acid is recovered. wherein R¹CO- represents a fatty acid residue having 8 to 22 carbon atoms; R² represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms; R³ represents an alkylene group having 1 to 5 carbon atoms; R⁴ represents an alkyl group having 1 to 4 carbon atoms; and M represents a monovalent cation.

  提供一种适用于工业生产的工艺，通过该工艺可以用廉价原料制备高纯度的 N-（长链酰基）氨基酸及其盐。 在碱性催化剂存在下，脂肪酸烷基酯 (2) 与氨基腈 (3) 反应生成脒腈 (1)，脒腈 (1) 在碱性物质存在下水解成 N-（长链酰基）氨基酸盐 (4)、用矿物酸将所得水溶液的 pH 值调节至 1 至 5，形成 N-（长链酰基）氨基酸 (5)，然后回收该氨基酸。 其中 R¹CO- 代表具有 8 至 22 个碳原子的脂肪酸残基；R² 代表氢原子或具有 1 至 3 个碳原子的烷基；R³ 代表具有 1 至 5 个碳原子的亚烷基；R⁴ 代表具有 1 至 4 个碳原子的烷基；M 代表一价阳离子。
• N-(long-chain acyl)amino nitrile and process for the preparation thereof
  申请人：Kao Corporation

  公开号：EP0649836B1

  公开（公告）日：1998-02-25
• VERFAHREN ZUR HERSTELLUNG VON SPHINGOLIPIDEN DURCH N-ACYLIERUNG VON LYSOSPHINGOLIPIDEN UNTER VERWENDUNG EINER LIPASE UND EINES FETTSÄUREGLYCERINESTERS
  申请人：Evonik Degussa GmbH

  公开号：EP2283144B1

  公开（公告）日：2017-11-08
• VERFAHREN ZUR HERSTELLUNG VON SPHINGOLIPIDEN DURCH N-ACYLIERUNG VON LYSOSPHINGOLIPIDEN UNTER VERWENDUNG EINER FUNGALEN LIPASE
  申请人：Evonik Degussa GmbH

  公开号：EP2283143B1

  公开（公告）日：2017-12-27