Formamino-(cyclopropylmethyl)-malonsaeure-diaethylester | 18941-95-2

• 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: Formamino-(cyclopropylmethyl)-malonsaeure-diaethylester
• 英文别名: cyclopropylmethyl-formylamino-malonic acid diethyl ester；Cyclopropylmethyl-formylamino-malonsaeure-diaethylester；Diethyl 2-(cyclopropylmethyl)-2-formamidopropanedioate
• CAS: 18941-95-2
• 化学式: C₁₂H₁₉NO₅
• 分子量: 257.287
• InChiKey: HTCQJUUDZBEYHH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  18
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 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：

  Formamino-(cyclopropylmethyl)-malonsaeure-diaethylester 在 氢溴酸 作用下， 生成 2-amino-3-cyclopropylpropanoic acid
  参考文献：
  名称：

  The Synthesis of β-Cyclopropyl-α-aminopropionic Acid

  摘要：

  DOI：

  10.1021/ja01629a101
• 作为产物：
  描述：

  甲酰氨基丙二酸二乙酯 生成 Formamino-(cyclopropylmethyl)-malonsaeure-diaethylester
  参考文献：
  名称：

  艾伦。第十九部分。（±）-高血糖素A的合成和天然异构体的构型

  摘要：

  描述了通过Simmons-Smith甲基化通过烯丙基中间体1-乙基甲酰基氨基戊3,4-二烯-1,1-二羧酸二乙酯合成次糖苷A的方法。用丁酸2，3-二烯丙酸乙酯和烯丙基（甲酰氨基）丙二酸二乙酯进行模型实验，得到亚甲基环丙烷甲酸乙酯，水解和脱羧后，得到2-氨基-3-环丙基丙酸。降糖素A降解为已知（S）-构型的（+）-3-甲基戊酸将其构型确定为（+）-（2 S：4 S）-2-氨基-4,5-甲基己基-5-烯酸。

  DOI：

  10.1039/j39680000288

文献信息

• Process for the preparation of enantiomerically-enriched cyclopropylalanine derivates
  申请人：——

  公开号：US20020049331A1

  公开（公告）日：2002-04-25

  Disclosed are processes for the preparation of enantiomerically-enriched cyclopropylalanine derivatives by the hydrogenation of certain enamides in the presence of a catalyst comprising a transition metal and a substantially enantiomerically-pure bis-phosphine catalyst and certain novel enamide ester compounds which are intermediates in the processes. The processes include novel 2-step and 3-step processes for the preparation of enantiomerically-enriched cyclopropylalanine derivatives. The two-step process comprises the steps of reacting cyclopropanecarboxaldehyde with a substituted phosphorylglycine to afford an enamide ester which then is hydrogenated in the presence of a catalyst comprising a transition metal and a substantially enantiomerically-pure bis-phosphine catalyst. The three-step process comprises the steps of forming an azlactone from an N-acylglycine and cyclopropanecarboxaldehyde, converting the azlactone to the aforesaid enamide which then is hydrogenated in the presence of a catalyst comprising a transition metal and a substantially enantiomerically-pure bis-phosphine catalyst.

  本发明公开了在由过渡金属和对映体纯度很高的双膦催化剂组成的催化剂存在下，通过氢化某些烯酰胺制备对映体富集的环丙基丙氨酸衍生物的工艺，以及作为工艺中间体的某些新型烯酰胺酯化合物。这些工艺包括用于制备对映体富集的环丙基丙氨酸衍生物的新型两步法和三步法工艺。两步法包括环丙基甲醛与取代的磷酰甘氨酸反应生成烯酰胺酯，然后在由过渡金属和对映体纯度很高的双膦催化剂组成的催化剂存在下进行氢化反应。该三步法包括以下步骤：由 N-酰基甘氨酸和环丙烷甲醛形成氮内酯，将氮内酯转化为上述烯酰胺，然后在由过渡金属和对映体纯度很高的双膦催化剂组成的催化剂存在下进行氢化。
• PREPARATION OF ENANTIOMERICALLY-ENRICHED CYCLOPROPYLALANINE DERIVATIVES
  申请人：EASTMAN CHEMICAL COMPANY

  公开号：EP1320518A2

  公开（公告）日：2003-06-25
• US6635784B2
  申请人：——

  公开号：US6635784B2

  公开（公告）日：2003-10-21
• [EN] PROCESS FOR THE PREPARATION OF ENANTIOMERICALLY-ENRICHED CYCLOPROPYLALANINE DERIVATIVES<br/>[FR] PROCEDE DE PREPARATION DE DERIVES DE CYCLOPROPYLALANINE ENANTIOMERIQUEMENT ENRICHIS
  申请人：EASTMAN CHEM CO

  公开号：WO2002026695A2

  公开（公告）日：2002-04-04

  Disclosed are processes for the preparation of enantiomerically-enriched cyclopropylalanine derivatives by the hydrogenation of certain enamides in the presence of a catalyst comprising a transition metal and a substantially enantiomerically-pure bis-phosphine catalyst and certain novel enamide eser compounds which are intermediates in the processes. The processes include novel 2-step and 3-step processes for the preparation of enantiomerically-enriched cyclopropylalanine derivatives. The two-step process comprises the steps of reacting cyclopropanecarboxaldehyde with a substituted phosphorylglycine to afford an enamide eser which then is hydrogenated in the presence of a catalyst comprising a transition metal and a substantially enantiomerically-pure bis-phosphine catalyst. The three-step process comprises the steps of forming an azlactone from an N-acylglycine and cyclopropanecarboxaldehyde, converting the azlactone to the aforesaid enamide which then is hydrogenated in the presence of a catalyst comprising a transition metal and a substantially enantiomerically-pure bis-phosphine catalyst.
• Allenes. Part XIX. Synthesis of (±)-hypoglycin A and configuration of the natural isomer
  作者：D. K. Black、S. R. Landor

  DOI：10.1039/j39680000288

  日期：——

  The synthesis of hypoglycin A by way of the allenic intermediate, diethyl 1-formylaminopenta-3,4-diene-1,1-dicarboxylate, by Simmons–Smith methylation, is described. Model experiments with ethyl buta-2,3-dienoate and diethyl allyl(formylamino)malonate gave ethyl methylenecyclopropanecarboxylate and, after hydrolysis and decarboxylation, 2-amino-3-cyclopropylpropionic acid. Degradation of hypoglycin

  描述了通过Simmons-Smith甲基化通过烯丙基中间体1-乙基甲酰基氨基戊3,4-二烯-1,1-二羧酸二乙酯合成次糖苷A的方法。用丁酸2，3-二烯丙酸乙酯和烯丙基（甲酰氨基）丙二酸二乙酯进行模型实验，得到亚甲基环丙烷甲酸乙酯，水解和脱羧后，得到2-氨基-3-环丙基丙酸。降糖素A降解为已知（S）-构型的（+）-3-甲基戊酸将其构型确定为（+）-（2 S：4 S）-2-氨基-4,5-甲基己基-5-烯酸。