rac-ethyl 3-cyanopentanoate | 150711-45-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: rac-ethyl 3-cyanopentanoate
• 英文别名: 3-cyano-valeric acid ethyl ester；3-Cyan-valeriansaeure-aethylester；ethyl 3-cyano-n-valerate；Ethyl 3-cyanopentanoate
• CAS: 150711-45-8
• 化学式: C₈H₁₃NO₂
• 分子量: 155.197
• InChiKey: HOHSJEOLBDROAJ-UHFFFAOYSA-N

物化性质

• 沸点：
  82-83 °C(Press: 2.2 Torr)
• 密度：
  0.983±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  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：
  0.75
• 拓扑面积：
  50.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  rac-ethyl 3-cyanopentanoate 在 一水合肼 作用下， 反应 240.0h， 以66%的产率得到5-Ethyl-6-hydrazinylidenediazinan-3-one
  参考文献：
  名称：

  β-氰基酯直接合成哒嗪环。四氢-3,6-哒嗪二酮3-腙衍生物的简便合成

  摘要：

  摘要 4-取代的四氢-3,6-哒嗪二酮 3-腙 (2)（或它们的 3-肼互变异构体 3）是合成双环哒嗪衍生物的有用中间体，在相应的烷基 3 反应中以令人满意的产率制备。用水合肼-取代的3-氰基丙酸酯。

  DOI：

  10.1080/00397919308011225
• 作为产物：
  描述：

  (Z)-ethyl 3-cyanopent-2-enoate 在 palladium 10% on activated carbon 、 氢气 作用下， 以 四氢呋喃 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 以97%的产率得到rac-ethyl 3-cyanopentanoate
  参考文献：
  名称：

  Chemoenzymatic Asymmetric Synthesis of Pregabalin Precursors via Asymmetric Bioreduction of β-Cyanoacrylate Esters Using Ene-Reductases

  摘要：

  The asymmetric bioreduction of a library of beta-cyanoacrylate esters using ene-reductases was studied with the aim to provide a biocatalytic route to precursors for GABA analogues, such as pregabalin. The stereochemical outcome could be controlled by substrate-engineering through size-variation of the ester moiety and by employing stereochemically pure (E)- or (Z)-isomers, which allowed to access both enantiomers of each product in up to quantitative conversion in enantiomerically pure form. In addition, stereoselectivities and conversions could be improved by mutant variants of OPR1, and the utility of the system was demonstrated by preparative-scale applications.

  DOI：

  10.1021/jo302484p

文献信息

• Process for production of 2,5 dioxopyrrolidine 3 carboxylate
  申请人：Tanaka Daisuke

  公开号：US20110190497A1

  公开（公告）日：2011-08-04

  The present invention provides a novel intermediate which enable to prepare tetrahydropyrrolo[1,2-a]pyrazin-4-spiro-3′-pyrrolidine derivatives such as Ranirestat being promising therapeutic agents for diabetic complications in a short process and in an economically advantageous and safe manner, and a process for preparing the same. That is, the present invention provides a process for preparing a compound of the following formula (I) wherein R 1 is an amino group protected with a protecting group, etc., and R 2 is a lower alkyl group, etc., comprising the following steps (1) and (2): (1) a step of converting a cyano group in a compound of the following formula (II) wherein n and m are each independently 0 or 1; provided when n is 0 and m is 1, then R 2 and R 3 are the same or different protecting groups for a carboxyl group; and when n is 1 and m is 0, then R 2 and R 3 are the same protecting groups for a carboxyl group; and R 1 is as defined above, into a carbamoyl group in the presence of divalent palladium compound(s), primary amide(s) and water; and (2) a step of cyclizing the product obtained in the step (1).

  本发明提供了一种新型的中间体，能够以简短的过程、经济上可行且安全的方式制备四氢吡咯[1,2-a]吡嗪-4-螺-3'-吡咯烷衍生物，例如Ranirestat，这是一种对糖尿病并发症有治疗前景的药物，以及一种制备该中间体的方法。即，本发明提供了一种制备如下公式(I)化合物的方法，其中R1是带有保护基团的氨基，R2是低级烷基等，包括以下步骤(1)和(2)：(1)将如下公式(II)化合物中的腈基转换为氨基甲酰基的步骤，其中n和m各自独立地为0或1；当n为0且m为1时，R2和R3是相同的或不同的羧基保护基团；当n为1且m为0时，R2和R3是羧基的相同保护基团；R1如上所述，该步骤中存在二价钯化合物、一级酰胺和水；(2)将步骤(1)中得到的产物环化的步骤。
• SILICON-CONTAINING CARBOXYLIC ACID DERIVATIVE
  申请人：Muratake Hideaki

  公开号：US20140031575A1

  公开（公告）日：2014-01-30

  A compound represented by the formula (I) [R 1 to R 8 represent an alkyl group, an alkenyl group, and the like; n represents 0 or 1; R 4 represents an amino group or —(CX 2 ) m —COOH (m represents 0 to 3, and X represents hydrogen atom); R 5 represents —(CY 2 ) p —COOR 6 (p represents an 0 to 3, Y represents hydrogen atom, and R 6 represents hydrogen atom or an alkyl group)], or a salt thereof.

  由式(I)表示的化合物[R1至R8表示烷基基团、烯基基团等；n表示0或1；R4表示氨基团或—(CX2)m—COOH（m表示0到3，X表示氢原子）；R5表示—(CY2)p—COOR6（p表示0到3，Y表示氢原子，R6表示氢原子或烷基基团）]，或其盐。
• Further Syntheses of Primaquine Analogs¹
  作者：Robert C. Elderfield、Elizabeth F. Claflin、Holly E. Mertel、Orville L. McCurdy、Richard T. Mitch、Charles D. Ver Nooy、Bruce H. Wark、Iris M. Wempen

  DOI：10.1021/ja01623a039

  日期：1955.9
• US8895769B2
  申请人：——

  公开号：US8895769B2

  公开（公告）日：2014-11-25
• Chemoenzymatic Asymmetric Synthesis of Pregabalin Precursors via Asymmetric Bioreduction of β-Cyanoacrylate Esters Using Ene-Reductases
  作者：Christoph K. Winkler、Dorina Clay、Simon Davies、Pat O’Neill、Paul McDaid、Sebastien Debarge、Jeremy Steflik、Mike Karmilowicz、John W. Wong、Kurt Faber

  DOI：10.1021/jo302484p

  日期：2013.2.15

  The asymmetric bioreduction of a library of beta-cyanoacrylate esters using ene-reductases was studied with the aim to provide a biocatalytic route to precursors for GABA analogues, such as pregabalin. The stereochemical outcome could be controlled by substrate-engineering through size-variation of the ester moiety and by employing stereochemically pure (E)- or (Z)-isomers, which allowed to access both enantiomers of each product in up to quantitative conversion in enantiomerically pure form. In addition, stereoselectivities and conversions could be improved by mutant variants of OPR1, and the utility of the system was demonstrated by preparative-scale applications.