4,4,4-trimethoxybutyronitrile | 133871-50-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4,4,4-trimethoxybutyronitrile
• 英文别名: 3-cyano-orthopropionic acid trimethyl ester；3-Cyan-orthopropionsaeure-trimethylester；4,4,4-Trimethoxybutanenitrile
• CAS: 133871-50-8
• 化学式: C₇H₁₃NO₃
• 分子量: 159.185
• InChiKey: GSUSVAUWAKSSGP-UHFFFAOYSA-N

物化性质

• 熔点：
  59-61 °C
• 沸点：
  73-74 °C(Press: 0.5 Torr)
• 密度：
  1.055 g/cm3(Temp: 25 °C)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  51.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4,4,4-trimethoxybutyronitrile 在 盐酸 作用下， 生成 3-氰基丙酸甲酯
  参考文献：
  名称：

  Ketene Acetals. XX. The Preparation and Properties of Cyanoketene Acetals. Some Novel Benzylation Reactions

  摘要：

  DOI：

  10.1021/ja01169a014
• 作为产物：
  描述：

  3-cyano-propionimidic acid methyl ester; hydrochloride 以65%的产率得到
  参考文献：
  名称：

  UENO, HIROAKI;MARUYAMA, AKIRA;MIYAKE, MOTOYOSHI;NAKAO, ETSUKO;NAKAO, KENI+, J. MED. CHEM., 34,(1991) N, C. 2468-2473

  摘要：

  DOI：

文献信息

• Synthesis and evaluation of antiinflammatory activities of a series of corticosteroid 17.alpha.-esters containing a functional group
  作者：Hiroaki Ueno、Akira Maruyama、Motoyoshi Miyake、Etsuko Nakao、Kenichiro Nakao、Kohei Umezu、Issei Nitta

  DOI：10.1021/jm00112a023

  日期：1991.8

  contain a functionalized ester group at 17 alpha has been prepared and examined to separate their systemic activity from topical antiinflammatory activity. Introduction of the functionalized ester group at 17 alpha was carried out by an acid-catalyzed formation of cyclic ortho esters with 17 alpha,21-hydroxyl groups of corticosteroids and subsequent acid-catalyzed hydrolysis. As for the functional group

  已经制备并检查了一系列在17α处含有官能化酯基的21-脱氧21-氯皮质类固醇，并将其全身活性与局部抗炎活性分开。通过酸催化形成具有皮质类固醇的17α，21-羟基的环状原酸酯，并随后进行酸催化的水解，来引入在17α的官能化酯基。至于官能团，在17个α-链烷酸酯基的末端碳原子上引入了氯，甲氧基，乙酰氧基，氰基，环丙基或烷氧羰基。检查了这些化合物的局部抗炎活性和全身活性，发现它们显着依赖于17种α-酯的功能。在这些衍生品中，一系列17种α-（烷氧基羰基）链烷酸酯（17α-OCO（CH2）nCOOR）表现出出色的全身活性与局部活性的分离。还研究了亚甲基数（n）和酯的烷基（R）对皮质类固醇衍生物的局部或全身活性的影响。
• Preparation of Gamma-Amino Acids Having Affinity for The Alpha-2-Delta Protein
  申请人：Evans Margaret Claire

  公开号：US20090299093A1

  公开（公告）日：2009-12-03

  Disclosed are materials and methods for preparing optically active γ-amino acids of Formula 1, which bind to the alpha-2-delta (α2δ) subunit of a calcium channel.

  本发明涉及一种制备结合到钙通道的α2δ亚基的光学活性γ-氨基酸的材料和方法，其化学式为1。
• Preparation of gamma-amino acids having affinity for the alpha-2-delta protein
  申请人：Pfizer Products Inc.

  公开号：EP2017259A2

  公开（公告）日：2009-01-21

  Disclosed are materials and methods for preparing optically active γ-amino acids of Formula 1, which bind to the alpha-2-delta (α2δ) subunit of a calcium channel.

  本发明公开了制备式 1 光学活性 γ 氨基酸的材料和方法、 与钙通道的α-2-δ（α2δ）亚基结合的材料和方法。
• Chemical Development of an α2δ Ligand, (3<i>S</i>,5<i>R</i>)-3-(Aminomethyl)-5-methyloctanoic Acid
  作者：Lorraine Murtagh、Catherine Dunne、Gino Gabellone、Niamh J. Panesar、Stuart Field、Lisa M. Reeder、James Saenz、George P. Smith、Kyle Kissick、Carlos, Martinez、John G. Van Alsten、Margaret C. Evans、Lloyd C. Franklin、Thomas Nanninga、John Wong

  DOI：10.1021/op2001832

  日期：2011.11.18

  Three synthetic approaches, suitable for the large scale manufacture of the alpha 2 delta-ligand, (3S,5R)-3-(aminomethyl)-5-methyloctanoic acid 3, have been evaluated. The selected seven step manufacturing process has then been optimized and used to deliver over 20 kg of API; salient features of the synthesis include the use of 4,4,4-trimethoxybutyronitrile as an efficient four carbon amino acid equivalent. Highly selective kinetic resolution of the C3 stereocente was accomplished via diastereoselective hydrolysis of a cyanoester intermediate using Amano Lipase PS-SD. Extensive process optimisation of the route starting from (R)-2-methylpentanol, led to significant improvements through telescoping, with less than 62 kg of solvent being needed to produce 1 kg of API.
• Ketene Acetals. XXVI. The Preparation and Properties of Some ι-Cyanoalkylketene Acetals
  作者：S. M. McElvain、Richard D. Mullineaux

  DOI：10.1021/ja01127a056

  日期：1952.4