dodecanal cyanohydrin | 4158-38-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: dodecanal cyanohydrin
• 英文别名: (RS)-2-hydroxy-tridecanenitrile；2-hydroxytridecanenitrile；2-Hydroxytridecanenitrile
• CAS: 4158-38-7
• 化学式: C₁₃H₂₅NO
• 分子量: 211.348
• InChiKey: BYFBRPSEKAGGBP-UHFFFAOYSA-N

物化性质

• 沸点：
  338.0±15.0 °C(predicted)
• 密度：
  0.901±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  15
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  44
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  dodecanal cyanohydrin 在 盐酸 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 水 为溶剂， 生成 (±)-2-羟基十三(烷)酸
  参考文献：
  名称：

  Enantioselective syntheses of (+)- and (–)-nephrosteranic acid employing the Nicholas-Schreiber reaction

  摘要：

  (+)和(-)-肾甾烷酸（16）已经通过一个三步反应序列以高对映选择性的方式从炔酸19（或ent-19）制备而成，该序列包括脱苄基化-内酯化、氧化裂解和C-4位的选择性异构化。酸19和ent-19通过Nicholas-Schreiber反应作为单一的对映异构体获得。

  DOI：

  10.1139/cjc-79-11-1727
• 作为产物：
  描述：

  十二醛 、 三甲基氰硅烷 在 三氟化硼乙醚 、 盐酸 、 水 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 12.0h， 以82%的产率得到dodecanal cyanohydrin
  参考文献：
  名称：

  5,5'-二烷基-6,6'-二氯-2, 2'-联吡啶的合成

  摘要：

  摘要 5,5'-二烷基-6,6'-二氯-2,2'-联吡啶以3-取代的2-氯-6-碘吡啶为原料，在钯催化偶联条件下合成。6-Alkyl-3,5-dichloro-2H-1,4-oxazin-2-ones 是合成这些功能化 2-iodo-6-chloropyridines 的优良前体。

  DOI：

  10.1080/00397910802440348

文献信息

• The first hydroxynitrile lyase catalysed cyanohydrin formation in ionic liquids
  作者：Richard P. Gaisberger、Martin H. Fechter、Herfried Griengl

  DOI：10.1016/j.tetasy.2004.06.028

  日期：2004.9

  Benzaldehyde, decanal, undecanal and dodecanal were reacted with hydrogen cyanide in a two phase solvent system aqueous buffer and ionic liquids (EMIMBF4)-B-., (PMIMBF4)-B-. and (BMIMBF4)-B-. in the presence of the hydroxynitrile lyases from Prunus amygdalus and Hevea brasiliensis. When compared to the use of organic solvents as the nonaqueous phase, the reaction rate was significantly increased whereas the enantioselectivity remained good. (C) 2004 Elsevier Ltd. All rights reserved.
• 1-Alkoxycarbonylalkylidenetriphenylarsoranes: Preparation and reactions
  作者：Josep Castells、Francisco López-Calahorra、Zhanru Yu

  DOI：10.1016/s0040-4020(01)85688-x

  日期：1994.1

  The higher homologues of the well-studied alkoxycarbonylmethylenetriphenylarsonium(1) ylide (3, R=H) can be easily obtained through the sequence: a). preparation of alkyl 2-trifloxyalkanoates (1); b), reaction between these trifloxyderivatives and triphenylphosphine to give 1-alkoxycarbonylalkyltriphenylarsonium triflates (2); and c), basic treatment of the triphenylarsonium triflates (2) with alumina-supported potassium fluoride to give 1-alkoxycarbonylalkyledenetriphenylarsonium ylides (3). These higher homologues of(3, R=H) react with aromatic aldehydes in good to excellent yields. and give rise to synthetically interesting ''coupling'' and cyclopropanation reactions.
• CO ₂ ‐Mediated Non‐Destructive Cyanide Wastewater Treatment
  作者：Allan R. Petersen、Martin Juhl、Aleksa Petrovic、Ji‐Woong Lee

  DOI：10.1002/ejoc.202100997

  日期：2021.9.21

  AbstractThe facile removal of cyanide anions from cyanide‐containing water was achieved using CO2 in conjunction with aldehydes which can be recycled from the process. The conversion of the cyanide ion into an insoluble cyanohydrin in water allowed the removal of cyanide and could be used as a method for treating cyanide contaminated wastewater and for recovering cyanide or cyanohydrins for further applications.
• 2-HYDROXY AND 4-HYDROXY GLYCOLIPIDS AND THEIR DERIVATIVES
  申请人：[en]GLYCOSURF, INC.

  公开号：WO2024137705A1

  公开（公告）日：2024-06-27

  Described are glycolipids having a saccharide moiety attached at the 2-position of the lipid chain (i.e., "2-hydroxy glycolipids"), glycolipids having a saccharide moiety attached at the 4-position of the lipid chain (i.e., "4-hydroxy glycolipids"), and derivatives thereof. Further described are synthetic methods for preparing 2-hydroxy glycolipids, 4-hydroxy glycolipids, and derivatives thereof.
• Enantioselective syntheses of (+)- and (–)-nephrosteranic acid employing the Nicholas-Schreiber reaction
  作者：Peter A. Jacobi、Prudencio Herradura

  DOI：10.1139/cjc-79-11-1727

  日期：——

  (+)- and (-)-Nephrosteranic acid (16) have been prepared in an enantioselective fashion from alkyne acid 19 (or ent-19) by a three step sequence involving debenzylation-lactonization, oxidative cleavage, and selective epimerization at C-4. Acids 19 and ent-19 were obtained as single enantiomers employing a Nicholas-Schreiber reaction.

  (+)和(-)-肾甾烷酸（16）已经通过一个三步反应序列以高对映选择性的方式从炔酸19（或ent-19）制备而成，该序列包括脱苄基化-内酯化、氧化裂解和C-4位的选择性异构化。酸19和ent-19通过Nicholas-Schreiber反应作为单一的对映异构体获得。