2-(1-Ethoxy-ethoxy)-malononitrile | 128302-77-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(1-Ethoxy-ethoxy)-malononitrile
• 英文别名: 2-(1-Ethoxyethoxy)-malononitrile；2-(1-ethoxyethoxy)propanedinitrile
• CAS: 128302-77-2
• 化学式: C₇H₁₀N₂O₂
• 分子量: 154.169
• InChiKey: NJALXPYXKAGPTQ-UHFFFAOYSA-N

物化性质

• 沸点：
  218.6±35.0 °C(Predicted)
• 密度：
  1.068±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  66
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(1-Ethoxy-ethoxy)-malononitrile 在 三乙胺 、 N,N-二异丙基乙胺 作用下， 生成 N-[2,2-dicyano-2-(1-ethoxyethoxy)-1-(4-methoxyphenyl)ethyl]-N-(methoxymethyl)-4-methylbenzenesulfonamide
  参考文献：
  名称：

  Development of a new acyl anion equivalent for the preparation of masked activated esters, and their use to prepare a dipeptide

  摘要：

  DOI：

  10.1021/jo00302a008
• 作为产物：
  描述：

  2-(1-Ethoxyethoxy)propanediamide 在 伯吉斯试剂 作用下， 以 四氢呋喃 为溶剂， 以74%的产率得到2-(1-Ethoxy-ethoxy)-malononitrile
  参考文献：
  名称：

  Development of a new acyl anion equivalent for the preparation of masked activated esters, and their use to prepare a dipeptide

  摘要：

  DOI：

  10.1021/jo00302a008

文献信息

• Synthesis of α-Amino Acid Precursors Directly from Aldehydes Using Masked Acyl Cyanide Reagents and N,O-Dialkylated Hydroxylamines
  作者：Hisao Nemoto、Rujian Ma、Tomoyuki Kawamura、Masaki Kamiya、Masayuki Shibuya

  DOI：10.1021/jo0607515

  日期：2006.8.1

  A synthetic methodology for the synthesis of α-amino acid precursors directly from the corresponding aldehydes using N,O-dialkylated hydroxylamines and masked acyl cyanide (MAC) reagents was developed. The one-pot reaction can be carried out under mild conditions and without a separate purification step of the imino species. The method was applied to the synthesis of optically pure (+)-4-methylphenylglycine

  开发了一种使用N，O-二烷基化羟胺和掩蔽的氰化氰（MAC）试剂直接从相应的醛合成α-氨基酸前体的合成方法。一锅法反应可以在温和的条件下进行，而无需单独的亚氨基物种纯化步骤。该方法以Abiko-Masamune的三环1,2-恶唑烷为手性助剂，用于光学纯的（+）-4-甲基苯基甘氨酸及其衍生物的合成。
• Palladium catalysed addition of masked formyl cyanides ROCH(CN)2 to aldehydes
  作者：Hisao Nemoto、Yasufumi Kubota、Yoshinori Yamamoto

  DOI：10.1039/c39940001665

  日期：——

  The palladium catalysed reactions of masked formyl cyanides 1 with aldehydes 2, followed by treatment with either diketene or acetic anhydride–pyridine, afford the addition products protected with acetylacetate 5 or acetyl group 6, respectively.

  掩蔽的甲酰氰1与醛2的钯催化反应，然后用二乙烯酮或乙酸酐-吡啶处理，分别得到用乙酰乙酸5或乙酰基6保护的加成产物。
• A three-step preparation of MAC reagents from malononitrile
  作者：Hisao Nemoto、Xinming Li、Rujian Ma、Ichiro Suzuki、Masayuki Shibuya

  DOI：10.1016/s0040-4039(02)02483-8

  日期：2003.1

  An alternative method for the preparation of MAC reagents, H-C(CN)2O-R, was developed. Using the proposed method, MAC reagents with acyl moiety were synthesized from malononitrile in more than 60% overall yields in three steps.

  开发了另一种制备MAC试剂的方法HC（CN）2 O-R。使用所提出的方法，通过三个步骤，由丙二腈以超过60％的总收率合成了具有酰基部分的MAC试剂。
• Transition Metal Catalyzed Addition of Certain Nucleophiles to Imines
  作者：Yoshinori Yamamoto、Yasufumi Kubota、Yoshihiro Honda、Hiroyuki Fukui、Naoki Asao、Hisao Nemoto

  DOI：10.1021/ja00086a071

  日期：1994.4
• Synthesis of 1,4-dicarbonyl compounds via the conjugate addition of a masked activated ester, ROCH(CN)2
  作者：Yasufumi Kubota、Hisao Nemoto、Yoshinori Yamamoto

  DOI：10.1021/jo00026a003

  日期：1991.12

  A new acyl anion equivalent for the preparation of masked activated esters, the protected hydroxymalonitrile 1, readily undergoes conjugate addition to alpha,beta-unsaturated carbonyl derivatives 2 to give the masked 1,4-dicarbonyl compounds 3 in good to high yields. 1,4-Dicarbonyl compounds 4, in which one of the two carbonyl groups has a reactivity different from the other, can be prepared selectively from 3.