2-Cyanoheptanoic acid | 855898-51-0

• 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: 2-Cyanoheptanoic acid
• CAS: 855898-51-0
• 化学式: C₈H₁₃NO₂
• 分子量: 155.197
• InChiKey: XTSQLMAUSOIUGX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 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：
  61.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-Cyanoheptanoic acid 在 吡啶 、 glutamate dehydrogenase 、 葡萄糖 、 Old Yellow Enzyme-3 、 乙酸酐 、 烟酰胺腺嘌呤双核苷酸磷酸盐 作用下， 以 aq. phosphate buffer 、 二甲基亚砜 为溶剂， 反应 24.0h， 生成
  参考文献：
  名称：

  Rationalisation of the stereochemical outcome of ene-reductase-mediated bioreduction of α,β-difunctionalised alkenes

  摘要：

  The OYE1-3-mediated reductions of some alpha,beta-difunctionalised alkenes, showing on the double bond a nitrile and ester group, are submitted to a careful stereochemical analysis, in order to identify which of the two electron-withdrawing groups (EWGs) is responsible for the activation of the C=C double bond towards reduction and for establishing hydrogen bond interactions within the binding pocket of the enzymes. The results show that for most of these substrates the activating EWG is the CN moiety linked to the prostereogenic olefinic carbon atom. The final stereochemical outcome can be explained through the empirical model which has been recently developed for difunctionalised alkenes activated by carbonyl/carboxyl containing EWGs.In a single case the activation is due to the COOR group linked to the less substituted olefinic carbon atom: an alternative empirical model is established for this kind of substrates, taking into consideration the OYE-catalysed reductions of beta,beta'-disubstituted-a-monofunctionalised alkenes. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2013.12.020
• 作为产物：
  描述：

  2-Cyan-hept-2-ensaeure 在 sodium tetrahydroborate 作用下， 以 水 为溶剂， 生成 2-Cyanoheptanoic acid
  参考文献：
  名称：

  Rationalisation of the stereochemical outcome of ene-reductase-mediated bioreduction of α,β-difunctionalised alkenes

  摘要：

  The OYE1-3-mediated reductions of some alpha,beta-difunctionalised alkenes, showing on the double bond a nitrile and ester group, are submitted to a careful stereochemical analysis, in order to identify which of the two electron-withdrawing groups (EWGs) is responsible for the activation of the C=C double bond towards reduction and for establishing hydrogen bond interactions within the binding pocket of the enzymes. The results show that for most of these substrates the activating EWG is the CN moiety linked to the prostereogenic olefinic carbon atom. The final stereochemical outcome can be explained through the empirical model which has been recently developed for difunctionalised alkenes activated by carbonyl/carboxyl containing EWGs.In a single case the activation is due to the COOR group linked to the less substituted olefinic carbon atom: an alternative empirical model is established for this kind of substrates, taking into consideration the OYE-catalysed reductions of beta,beta'-disubstituted-a-monofunctionalised alkenes. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2013.12.020

文献信息

• [EN] PROCESS FOR PREPARING ELECTRON DEFICIENT OLEFIN PRECURSORS<br/>[FR] PROCÉDÉ DE PRÉPARATION DE PRÉCURSEURS D'OLÉFINES DÉFICIENTES EN ÉLECTRONS
  申请人：HENKEL IP & HOLDING GMBH

  公开号：WO2018114463A1

  公开（公告）日：2018-06-28

  This invention relates to a process for producing electron deficient olefin precursors, such as 2-cyanoacetates, using an acid catalyzed transesterification reaction.

  本发明涉及一种用于制备缺电子烯烃前体（如2-氰基乙酸酯）的过程，该过程使用酸催化的酯交换反应。
• [EN] PROCESS FOR PREPARING ELECTRON DEFICIENT OLEFINS<br/>[FR] PROCÉDÉ DE PRÉPARATION D'OLÉFINES DÉFICIENTES EN ÉLECTRONS
  申请人：HENKEL IP & HOLDING GMBH

  公开号：WO2018114460A1

  公开（公告）日：2018-06-28

  This invention relates to a process for preparing electron deficient olefins, such as 2-cyanoacrylates, using an acid catalyzed two-step process including an esterification reaction followed by a Knoevenagel condensation reaction.

  这项发明涉及一种制备电子亏损烯烃（如2-氰基丙烯酸酯）的过程，采用酸催化的两步法，包括酯化反应，然后是Knoevenagel缩合反应。
• Process for preparing electron deficient olefin precursors
  申请人：Henkel IP & Holding GmbH

  公开号：US10822303B2

  公开（公告）日：2020-11-03

  This invention relates to a process for producing electron deficient olefin precursors, such as 2-cyanoacetates, using an acid catalyzed transesterification reaction.

  本发明涉及一种利用酸催化酯交换反应生产缺电子烯烃前体（如 2-氰基乙酸酯）的工艺。
• Process for preparing electron deficient olefins
  申请人：Henkel IP & Holding GmbH

  公开号：US10913707B2

  公开（公告）日：2021-02-09

  This invention relates to a process for preparing electron deficient olefins, such as 2-cyanoacrylates, using an acid catalyzed two-step process including an esterification reaction followed by a Knoevenagel condensation reaction.

  本发明涉及一种利用酸催化两步法制备缺电子烯烃（如 2-氰基丙烯酸酯）的工艺，该工艺包括酯化反应和克努瓦纳格尔缩合反应。
• Asymmetric Michael and Aldol additions using bifunctional cinchona-alkaloid-based catalysts
  申请人：Deng Li

  公开号：US20060014956A1

  公开（公告）日：2006-01-19

  One aspect of the present invention relates to quinine-based and quinidine-based catalysts. Another aspect of the invention relates to a method of preparing a derivatized quinine-based or quinidine-based catalyst comprising 1) reacting quinine or quinidine with base and a compound that has a suitable leaving group, and 2) converting the ring methoxy group to a hydroxy group. Another aspect of the present invention relates to a method of preparing a chiral, non-racemic compound from a prochiral electron-deficient alkene or azo compound or prochiral aldehyde or prochiral ketone, comprising the step of: reacting a prochiral electron-deficient alkene or azo compound or prochiral aldehyde or prochiral ketone with a nucleophile in the presence of a catalyst; thereby producing a chiral, non-racemic compound; wherein said catalyst is a derivatized quinine or quinidine. Another aspect of the present invention relates to a method of kinetic resolution, comprising the step of: reacting racemic chiral alkene with a nucleophile in the presence of a derivatized quinine or quinidine.

  本发明的一个方面涉及奎宁基和奎尼丁基催化剂。本发明的另一方面涉及一种制备衍生化的奎宁基或奎尼丁基催化剂的方法，该方法包括 1) 奎宁或奎尼丁与碱和具有合适离去基团的化合物反应，以及 2) 将环甲氧基转化为羟基。本发明的另一方面涉及一种用手性缺电子烯烃或偶氮化合物或手性醛或手性酮制备手性非外消旋化合物的方法，包括以下步骤：在催化剂存在下，使手性缺电子烯烃或偶氮化合物或手性醛或手性酮与亲核体反应，从而生成手性非外消旋化合物；其中所述催化剂为衍生化的奎宁或奎尼丁。本发明的另一方面涉及一种动力学解析方法，包括以下步骤：外消旋手性烯与亲核体在衍生化奎宁或奎尼丁存在下反应。