3-propyl-1,5-pentanedinitrile | 444102-67-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 3-propyl-1,5-pentanedinitrile
• 英文别名: 3-Propylpentanedinitrile
• CAS: 444102-67-4
• 化学式: C₈H₁₂N₂
• 分子量: 136.197
• InChiKey: JOVKSMIJWSHUFN-UHFFFAOYSA-N

物化性质

• 沸点：
  301.2±15.0 °C(Predicted)
• 密度：
  0.921±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  47.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-propyl-1,5-pentanedinitrile 在 盐酸 作用下， 反应 4.0h， 生成 3-丙基戊二酸
  参考文献：
  名称：

  Arnarp; Enzell; Petersson, Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1986, vol. 40, # 10, p. 839 - 854

  摘要：

  DOI：
• 作为产物：
  描述：

  2-propyl-1,3-propanediol 1,3-dimesylate 、 氰化钾 以 二甲基亚砜 为溶剂， 反应 16.0h， 以98%的产率得到3-propyl-1,5-pentanedinitrile
  参考文献：
  名称：

  Pheromones and analogs from Neozeleboria wasps and the orchids that seduce them: a versatile synthesis of 2,5-dialkylated 1,3-cyclohexanediones

  摘要：

  Chiloglottone, a wasp pheromone and attractant of sexually deceptive Chiloglottis orchids, and several structural analogs were synthesized. The synthetic approach is facile, high yielding and versatile, enabling rapid divergence to generate dialkylated analogs of chiloglottone. The key transformation was an organocadmium-mediated desymmetrization of glutaric anhydride derivatives. This library of synthetic 2,5-dialkylated 1,3-cyclohexanediones may assist in future identification of natural products in further species. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.02.037

文献信息

• Inverting the Enantiopreference of Nitrilase‐Catalyzed Desymmetric Hydrolysis of Prochiral Dinitriles by Reshaping the Binding Pocket with a Mirror‐Image Strategy
  作者：Shanshan Yu、Jinlong Li、Peiyuan Yao、Jinhui Feng、Yunfeng Cui、Jianjiong Li、Xiangtao Liu、Qiaqing Wu、Jianping Lin、Dunming Zhu

  DOI：10.1002/anie.202012243

  日期：2021.2.15

  obtained. The mutant enzyme was applied in the preparation of optically pure (R)‐3‐isobutyl‐4‐cyanobutanoic acid ((R)‐2 a) and showed similar stereopreference inversion towards a series of 3‐substituted glutaronitriles. This study may offer a general strategy to switch the stereopreference of other nitrilases and other enzymes toward the desymmetric reactions of prochiral substrates with two identical

  应用镜像策略，即对底物结合袋进行对称分析，以鉴定两个关键的氨基酸残基W170和V198，这些残基可能会调节拟蓝藻中腈水解酶的对映体。PCC6803朝向3-异丁基戊二腈（1 a）。这两个残基的交换导致对映体优先转化（S，90％ee到R，47％ee）。通过常规位点饱和和组合诱变进一步重塑底物结合口袋，可以获得具有更高活性和立体选择性（99％ee，R）的变体E8。突变酶用于制备光学纯的（R）-3-异丁基-4-氰基丁酸（（R）-2 a），并显示出类似的立体偏爱，可逆于一系列3取代的戊二腈。这项研究可能提供一种一般策略，将其他腈水解酶和其他酶的立体偏好转换为具有两个相同反应性官能团的前手性底物的不对称反应。
• Arnarp; Enzell; Petersson, Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1986, vol. 40, # 10, p. 839 - 854
  作者：Arnarp、Enzell、Petersson、Pettersson

  DOI：——

  日期：——
• Pheromones and analogs from Neozeleboria wasps and the orchids that seduce them: a versatile synthesis of 2,5-dialkylated 1,3-cyclohexanediones
  作者：Jacqueline Poldy、Rod Peakall、Russell A. Barrow

  DOI：10.1016/j.tetlet.2008.02.037

  日期：2008.4

  Chiloglottone, a wasp pheromone and attractant of sexually deceptive Chiloglottis orchids, and several structural analogs were synthesized. The synthetic approach is facile, high yielding and versatile, enabling rapid divergence to generate dialkylated analogs of chiloglottone. The key transformation was an organocadmium-mediated desymmetrization of glutaric anhydride derivatives. This library of synthetic 2,5-dialkylated 1,3-cyclohexanediones may assist in future identification of natural products in further species. (C) 2008 Elsevier Ltd. All rights reserved.