triethyl 2-cyano-1,2,3-propanetricarboxylate | 20822-61-1

• 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: triethyl 2-cyano-1,2,3-propanetricarboxylate
• 英文别名: Triethyl 2-cyanopropane-1,2,3-tricarboxylate
• CAS: 20822-61-1
• 化学式: C₁₃H₁₉NO₆
• 分子量: 285.297
• InChiKey: XMHQEXOBYGDRCG-UHFFFAOYSA-N

物化性质

• 熔点：
  40-41 °C
• 沸点：
  120-125 °C(Press: 0.04 Torr)
• 密度：
  1.155±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  20
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  103
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  triethyl 2-cyano-1,2,3-propanetricarboxylate 在 水 、 sodium chloride 作用下， 以 二甲基亚砜 为溶剂， 反应 4.0h， 以83%的产率得到3-cyanopentane-1,5-dioic acid diethyl ester
  参考文献：
  名称：

  Synthesis of polyfunctional aliphatic carbonyl compounds under phase-transfer conditions

  摘要：

  We have studied mono- and dialkylation of malonic, acetoacetic, and cyanoacetic esters with esters of haloacetic and beta-halopropionic acids and addition of the CH acids mentioned and their analogs to methyl and ethyl acrylate under phase-transfer catalysis conditions, and also deethoxycarbonylation of the obtained products. We have demonstrated for the first time the possibility of Dieckmann cyclization under phase-transfer catalysis conditions and have developed a simple method for the synthesis of 2,3-di(ethoxycarbonyl)cyclopentanone, a key intermediate in the syntheis of deoxyprostaglandins, by cyclization of triethyl 1,2,4-butanetricarboxylate.

  DOI：

  10.1007/bf00961357
• 作为产物：
  描述：

  氰乙酸乙酯 在 sodium hydride 作用下， 反应 13.0h， 生成 triethyl 2-cyano-1,2,3-propanetricarboxylate
  参考文献：
  名称：

  Absolute configuration of 2,7-diazaspiro[4,4]nonane. A reassignment

  摘要：

  DOI：

  10.1021/jo00326a031

文献信息

• [EN] PROCESS AND EQUIPMENT FOR THE PREPARATION OF HALOCARBOXYLIC ACID ALKYL ESTERS<br/>[FR] PROCÉDÉ ET MATÉRIEL POUR LA PRÉPARATION D'ESTERS ALKYLIQUES D'ACIDES CARBOXYLIQUES HALOGÉNÉS
  申请人：LONZA AG

  公开号：WO2013121017A1

  公开（公告）日：2013-08-22

  Provided is a reactive distillation and equipment to obtain a compound of formula (II) Hal-CH2-A-C(O)-OR, wherein Hal is halogen selected from F, CI, Br or I, A denotes a bond or a divalent spacer selected from alkylene and arylene groups, and R is C1-4 alkyl group.

  提供了一种反应蒸馏和设备，用于获得化合物的公式（II）Hal-CH2-A-C(O)-OR，其中Hal是从F、CI、Br或I中选择的卤素，A表示从烷基和芳基组中选择的键或二价间隔物，R是C1-4烷基基团。
• [EN] SYNTHESIS OF CYANOCARBOXYLIC ACID ALKYL ESTERS<br/>[FR] SYNTHÈSE D'ESTERS ALKYLIQUES D'ACIDES CYANOCARBOXYLIQUES
  申请人：LONZA AG

  公开号：WO2013121018A1

  公开（公告）日：2013-08-22

  Provided is a process for obtaining a compound of formula (I): N≡C-CH2-A-C(O)-OR, wherein Hal is halogen selected from F, Cl, Br or I, A denotes a bond or a divalent spacer selected from alkylene and arylene groups, and R is a C1-4 alkyl group, by reacting a compound of formula (II): Hal-CH2-A-C(O)-OR, wherein Hal is a halogen atom selected from F, Cl, Br and I, and wherein A and R are as defined above, with hydrogen cyanide in the presence of a first base, wherein the molar ratio between hydrogen cyanide and said first base is from 1:0.3 to 1:0.95 and the molar ratio between hydrogen cyanide to the compound of formula (II) is at least 1:1.

  提供了一种获得化合物的过程，其化学式为（I）：N≡C-CH2-A-C(O)-OR，其中Hal是从F、Cl、Br或I中选择的卤素，A表示从烷基和芳基组中选择的键或二价间隔基，R是C1-4烷基基团，通过将化合物（II）：Hal-CH2-A-C(O)-OR与氢氰酸在第一碱存在下反应获得，其中Hal是从F、Cl、Br和I中选择的卤素原子，A和R如上所定义，在氢氰酸和所述第一碱之间的摩尔比为1:0.3至1:0.95，氢氰酸与化合物（II）的摩尔比至少为1:1。
• Synthesis of a γ-Lactam Library via Formal Cycloaddition of Imines and Substituted Succinic Anhydrides
  作者：Darlene Q. Tan、Amy L. Atherton、Austin J. Smith、Cristian Soldi、Katherine A. Hurley、James C. Fettinger、Jared T. Shaw

  DOI：10.1021/co2001873

  日期：2012.3.12

  Formal cycloaddition reactions between imines and cyclic anhydrides serve as starting point for the synthesis of diverse libraries of small molecules. The synthesis of succinic anhydrides substituted with electron-withdrawing groups is facilitated by new mild conditions for alkylation of aryl-substituted acetyl esters with ethyl bromoacetate. These anhydrides are then used in formal cycloaddition reactions

  亚胺和环状酸酐之间的正式环加成反应是合成各种小分子文库的起点。新的温和条件促进了用吸电子基团取代的琥珀酸酐的合成，该条件为芳基取代的乙酰基酯与溴乙酸乙酯的烷基化提供了新的温和条件。然后将这些酸酐用于与亚胺的正式环加成反应中，以生成γ-内酰胺。2-氟-5-硝基苯基琥珀酸酐与亚胺有效反应，生成内酰胺，内酰胺进一步通过将硝基转化为苯胺和叠氮化物而进一步多样化，以分别与酰化剂和炔烃进行后续反应。首次报道了氰基琥珀酸酐的合成，
• Quinolone antibacterial agents substituted at the 7-position with spiroamines. Synthesis and structure-activity relationships
  作者：Townley P. Culbertson、Joseph P. Sanchez、Laura Gambino、Josephine A. Sesnie

  DOI：10.1021/jm00170a035

  日期：1990.8

  A series of fluoroquinolone antibacterials having the 7-position (10-position of pyridobenzoxazines) substituted with 2,7-diazaspiro[4.4]nonane (4b), 1,7-diazaspiro[4.4]nonane (5a), or 2,8-diazaspiro[5.5]undecane (6b) was prepared, and their biological activities were compared with piperazine and pyrrolidine substituted analogues. Most exhibited potent Gram-positive and Gram-negative activity, especially when side chain 4b was N-alkylated.
• Bone; Sprankling, Journal of the Chemical Society, 1902, vol. 81, p. 35
  作者：Bone、Sprankling

  DOI：——

  日期：——