(RS)-2-hydroxy-dodecanenitrile | 130273-76-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (RS)-2-hydroxy-dodecanenitrile
• 英文别名: 2-Hydroxydodecannitril；Undecanalcyanhydrin；2-hydroxydodecanenitrile
• CAS: 130273-76-6
• 化学式: C₁₂H₂₃NO
• 分子量: 197.321
• InChiKey: UWERQQFURZCSND-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  14
• 可旋转键数：
  9
• 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：

  (RS)-2-hydroxy-dodecanenitrile 在 对甲苯磺酸 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 2.25h， 生成 <2R-(2a(R*),3aα,4α,7α,7aα)>-2-methyl-8-<(octahydro-7,8,8-trimethyl-4,7-methanobenzofuran-2-yl)oxy>octadecan-7-on
  参考文献：
  名称：

  Pheromone, 3.Mitt.: Eine einfache Methode zur Steuerung der Reduktion von ?-Alkoxy-carbonylverbindungen

  摘要：

  Enantiomerically pure 1,2-diols bearing optionally syn or anti configurated secondary hydroxylic groups are synthesized from acetal-protected cyanohydrins. After resolution of the diastereomers the cyanohydrins are converted into alpha-alkoxy-ketones by Grignard-reaction followed by reduction using common chelating or non-chelating agents. Among others syntheses of enantiomerically pure pheromones, endo-Brevicomin, exo-Brevicomin and Dispalure are given as examples.

  DOI：

  10.1007/bf00810831
• 作为产物：
  描述：

  十一醛 、 丙酮氰醇 在 titanium(IV) isopropylate 作用下， 反应 21.0h， 以100%的产率得到(RS)-2-hydroxy-dodecanenitrile
  参考文献：
  名称：

  Cyano Group Transfer of Acetone Cyanohydrin to Aldehyde Mediated by Titanium Alkoxide and Aluminum Alkyls

  摘要：

  在钛烷氧化物和铝烷基物的存在下，丙酮氰醇对各种醛的氰基转移反应得以进行，高效地生成了相应的醛氰醇。

  DOI：

  10.1246/cl.1990.1171

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.
• Pheromone, 1. Mitt.: (+)-cis-Disparlure: Synthese und Feldtests
  作者：Christian R. Noe、Max Knollm�ller、Helmut K�rner、Gerhard Steinbauer、Helmut Koberg、Peter G�rtner

  DOI：10.1007/bf00815171

  日期：——

  A synthesis of (+)-cis-disparlure is described starting from racemic 2-hydroxy-dodecan-nitrile (2), which is transformed into the O-protected enantiomerically pure cyanohydrine 4. Grignard-reaction followed by reduction with BH3.(CH3)2S yields the corresponding threo-configurated secondary alcohol 10. After tosylation and cleavage of the MBE-protective-group (+)-cis-disparlure (14) is obtained by treatment with KOH. Mating disruption field tests exhibited a significantly increased effectiveness of (+)-cis-disparlure as compared to the racemic product.
• MORI, ATSUNORI;KINOSHITA, KOICHI;OSAKA, MASAHIKO;INOUE, SHOHEI, CHEM. LETT.,(1990) N, C. 1171-1172
  作者：MORI, ATSUNORI、KINOSHITA, KOICHI、OSAKA, MASAHIKO、INOUE, SHOHEI

  DOI：——

  日期：——
• NOE, CHRISTIAN R.;KNOLLMULLER, MAX;KURNER, HELMUT;STEINBAUER, GERHARD;KOB+, MONATSH. CHEM., 122,(1991) N-2, C. 101-110
  作者：NOE, CHRISTIAN R.、KNOLLMULLER, MAX、KURNER, HELMUT、STEINBAUER, GERHARD、KOB+

  DOI：——

  日期：——
• 2,2-DICHLORALKANCARBONSÄUREN, VERFAHREN ZU IHRER HERSTELLUNG DIESE ENTHALTENDE ARZNEIMITTEL, UND IHRE VERWENDUNG ZUR BEHANDLUNG DER INSULINRESISTENZ
  申请人：BOEHRINGER MANNHEIM GMBH

  公开号：EP0790824A1

  公开（公告）日：1997-08-27