rac-dimethyl 2-formamidosuccinate | 2311-19-5

• 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: rac-dimethyl 2-formamidosuccinate
• 英文别名: N-Formyl-asparaginsaeure-dimethylester；N-Formyl-asparaginsaeure-methylester；Dimethyl 2-formamidobutanedioate
• CAS: 2311-19-5
• 化学式: C₇H₁₁NO₅
• 分子量: 189.168
• InChiKey: LDHWRRAXFUAITF-UHFFFAOYSA-N

物化性质

• 沸点：
  353.8±32.0 °C(Predicted)
• 密度：
  1.200±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  81.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  rac-dimethyl 2-formamidosuccinate 在 三乙胺 、 三氯氧磷 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 50.0h， 生成 Dimethyl 2-[5-[1-(benzylamino)-2-methylpropyl]tetrazol-1-yl]butanedioate
  参考文献：
  名称：

  New cleavable isocyanides for the combinatorial synthesis of α-amino acid analogue tetrazoles

  摘要：

  3-Substituted 3-isocyano propionates as new cleavable isocyanides in combinatorial tetrazole synthesis via Ugi-reaction are introduced. The obtained 5-substituted tetrazoles are transformed into carboxylic acid isosteric 5-substituted 1H-tetrazoles under basic cleavage conditions. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.08.101
• 作为产物：
  描述：

  4-甲基DL-天冬氨酸氢酯 在 氯化亚砜 、 三乙胺 作用下， 反应 18.0h， 生成 rac-dimethyl 2-formamidosuccinate
  参考文献：
  名称：

  Triple Role of Phenylselenonyl Group Enabled a One-Pot Synthesis of 1,3-Oxazinan-2-ones From α-Isocyanoacetates, Phenyl Vinyl Selenones, and Water

  摘要：

  Reaction of alpha-substituted alpha-isocyanoacetates with phenyl vinyl selenones in the presence of a catalytic amount of base (DBU or Et3N, 0.05-0.1 equiv) followed by addition of p-toluenesulfonic acid (PTSA, 0.1-0.2 equiv) afforded 4,4,5-trisubstituted 1,3-oxazinan-2-ones in good to excellent yields. Enantiomerically enriched heterocycles can also be prepared using a Cinchona alkaloid-derived bifunctional organocatalyst for the Michael addition step. The phenylselenonyl group served as an activator for the Michael addition, a leaving group and a latent oxidant in this integrated reaction sequence.

  DOI：

  10.1021/ja506031h

文献信息

• Stereo-Controlled Asymmetric Bioreduction of α,β-Dehydroamino Acid Derivatives
  作者：Clemens Stueckler、Christoph K. Winkler、Mélanie Hall、Bernhard Hauer、Melanie Bonnekessel、Klaus Zangger、Kurt Faber

  DOI：10.1002/adsc.201100042

  日期：2011.5.9

  α,β‐Dehydroamino acid derivatives proved to be a novel substrate class for ene‐reductases from the ‘old yellow enzyme’ (OYE) family. Whereas N‐acylamino substituents were tolerated in the α‐position, β‐analogues were generally unreactive. For aspartic acid derivatives, the stereochemical outcome of the bioreduction using OYE3 could be controlled by variation of the N‐acyl protective group to furnish

  事实证明，α，β-脱氢氨基酸衍生物是“老黄酶”（OYE）家族中烯类还原酶的新型底物类别。而N-酰氨基取代基是在α位的耐受性，β-类似物普遍不反应。对于天冬氨酸衍生物，使用OYE3进行生物还原的立体化学结果可通过改变N-酰基保护基来提供相应的（S）-或（R）-氨基酸衍生物来控制。立体偏爱的这种转变是通过交换活化酯基团来改变底物结合力来解释的，这已通过2 H标记实验得到了证明。
• Inhibitors of serine proteases
  申请人：VERTEX PHARMACEUTICALS INCORPORATED

  公开号：EP2366704A1

  公开（公告）日：2011-09-21

  The present invention relates to compounds of formula (I): or pharmaceutically acceptable salts or mixture thereof that inhibit serine protease activity, particularly the activity of hepatitis C virus NS3-NS4A protease.

  本发明涉及式（I）化合物：或其药学上可接受的盐或混合物，可抑制丝氨酸蛋白酶活性，特别是丙型肝炎病毒 NS3-NS4A 蛋白酶的活性。
• Losse,G. et al., Zeitschrift fur Naturforschung. Teil B. Anorganische Chemie, organische Chemie, Biochemie, Biophysik, Biologie, 1962, vol. 17, p. 785 - 786
  作者：Losse,G. et al.

  DOI：——

  日期：——
• Heyns,K.; Gruetzmacher,H.-F., Zeitschrift fur Naturforschung. Teil B. Anorganische Chemie, organische Chemie, Biochemie, Biophysik, Biologie, 1961, vol. 16, p. 293 - 298
  作者：Heyns,K.、Gruetzmacher,H.-F.

  DOI：——

  日期：——
• Peptides having endothelin antagonist activity, a process for preparation thereof and pharmaceutical compositions comprising the same
  申请人：FUJISAWA PHARMACEUTICAL CO., LTD.

  公开号：EP0457195B1

  公开（公告）日：1998-04-15