(+/-)-5-benzoyloxy-2-hydroxypentanenitrile | 804556-30-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (+/-)-5-benzoyloxy-2-hydroxypentanenitrile
• 英文别名: (4-cyano-4-hydroxybutyl) benzoate
• CAS: 804556-30-7
• 化学式: C₁₂H₁₃NO₃
• 分子量: 219.24
• InChiKey: ZAJXXNDQDCSWAK-UHFFFAOYSA-N

物化性质

• 沸点：
  424.1±35.0 °C(Predicted)
• 密度：
  1.187±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.51
• 重原子数：
  16.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  70.32
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (+/-)-5-benzoyloxy-2-hydroxypentanenitrile 在 sodium hydroxide 、 4 A molecular sieve 作用下， 以 甲醇 为溶剂， 反应 120.0h， 生成 (+/-)-5-acetoxy-2-hydroxypentanenitrile
  参考文献：
  名称：

  Enzymatic acylation reactions on ω-hydroxycyanohydrins

  摘要：

  The enzymatic acylation of certain omega-hydroxycyanohydrins protected a, the primary alcohol has been studied. The best enantioselectivities are obtained with Pseudomonas cepacia lipase (PSL-C) and Candida antarctica lipase A (CAL-A), for the omega-O-tritylated cyanohydrins. The effect of the protecting group in the enzymatic reactions has been studied using molecular modeling. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.06.134
• 作为产物：
  描述：

  苯甲酰氯 、 2,5-dihydroxypentanenitrile 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以64%的产率得到(+/-)-5-benzoyloxy-2-hydroxypentanenitrile
  参考文献：
  名称：

  Enzymatic acylation reactions on ω-hydroxycyanohydrins

  摘要：

  The enzymatic acylation of certain omega-hydroxycyanohydrins protected a, the primary alcohol has been studied. The best enantioselectivities are obtained with Pseudomonas cepacia lipase (PSL-C) and Candida antarctica lipase A (CAL-A), for the omega-O-tritylated cyanohydrins. The effect of the protecting group in the enzymatic reactions has been studied using molecular modeling. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.06.134

文献信息

• Mild Base Promoted Nucleophilic Substitution of Unactivated <i>sp</i> ³ ‐Carbon Electrophiles with Alkenylboronic Acids
  作者：Shiwen Liu、Xiaojun Zeng、Gerald B. Hammond、Bo Xu

  DOI：10.1002/adsc.201800826

  日期：2018.10.4

  Diverse alkenylboronic acids react smoothly with various sp3‐carbon electrophiles such as unactivated alkyl triflates in the presence of mild bases such as K3PO4. The reaction protocol is very mild and thereby enables high functional group tolerance. This transition metal‐free condition is orthogonal towards the classic transition metal catalyzed Suzuki coupling.

  在温和的碱（例如K 3 PO 4）存在下，不同的烯基硼酸与各种sp 3-碳亲电试剂（例如未活化的烷基三氟甲磺酸酯）平滑反应。反应方案非常温和，因此可以实现较高的官能团耐受性。这种无过渡金属的条件与经典的过渡金属催化的Suzuki偶联正交。
• Nickel‐Catalyzed, Reductive C(sp ³ )−Si Cross‐Coupling of α‐Cyano Alkyl Electrophiles and Chlorosilanes
  作者：Liangliang Zhang、Martin Oestreich

  DOI：10.1002/anie.202107492

  日期：2021.8.16

  A nickel/zinc-catalyzed cross-electrophile coupling of alkyl electrophiles activated by an α-cyano group and chlorosilanes is reported. Elemental zinc is the stoichiometric reductant in this reductive coupling process. By this, a C(sp3)−Si bond can be formed starting from two electrophilic reactants whereas previous methods rely on the combination of carbon nucleophiles and silicon electrophiles or

  报道了由 α-氰基和氯硅烷活化的烷基亲电试剂在镍/锌催化下的交叉亲电偶联。元素锌是该还原偶联过程中的化学计量还原剂。由此，可以从两种亲电反应物开始形成C(sp 3 )-Si键，而之前的方法依赖于碳亲核试剂和硅亲电试剂的组合，反之亦然。