butyl 2-cyano-11-hydroxyundecanoate | 1208130-90-8

• 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: butyl 2-cyano-11-hydroxyundecanoate
• CAS: 1208130-90-8
• 化学式: C₁₆H₂₉NO₃
• 分子量: 283.411
• InChiKey: KFMZBRLIAHPTAC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  20
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  70.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1,9-壬二醇 、 氰乙酸正丁酯 在 bis(1,5-cyclooctadiene)diiridium(I) dichloride 、 三苯基膦 作用下， 以 1,4-二氧六环 为溶剂， 反应 20.0h， 以59%的产率得到butyl 2-cyano-11-hydroxyundecanoate
  参考文献：
  名称：

  Synthesis of ω-Hydroxy Carboxylic Acids and α,ω-Dimethyl Ketones Using α,ω-Diols As Alkylating Agents

  摘要：

  Synthesis of omega-hydroxy carboxylic acids and alpha,omega-dimethyl diketones was successfully achieved by using alpha,omega-diols as alkylating agents under the influence of an iridium catalyst. For example, the alkylation of butyl cyanoacetate with 1,13-tridecanediol in the presence of [IrCl(cod)](2) or [IrCl(coe)(2)](2) gave rise to butyl 2-cyano-15-hydroxypentadecanoate in good yield which is easily converted to cyclopentadecanolide (CPDL). In addition, the alkylation of acetone with 1,10-decanediol in the presence of [IrCl(cod)](2) and KOH resulted in an important muscone precursor, 2,15-hexadecanedione (HDDO), in good yield.

  DOI：

  10.1021/jo9027165

文献信息

• Synthesis of ω-Hydroxy Carboxylic Acids and α,ω-Dimethyl Ketones Using α,ω-Diols As Alkylating Agents
  作者：Yosuke Iuchi、Megumi Hyotanishi、Brittany E. Miller、Kensaku Maeda、Yasushi Obora、Yasutaka Ishii

  DOI：10.1021/jo9027165

  日期：2010.3.5

  Synthesis of omega-hydroxy carboxylic acids and alpha,omega-dimethyl diketones was successfully achieved by using alpha,omega-diols as alkylating agents under the influence of an iridium catalyst. For example, the alkylation of butyl cyanoacetate with 1,13-tridecanediol in the presence of [IrCl(cod)](2) or [IrCl(coe)(2)](2) gave rise to butyl 2-cyano-15-hydroxypentadecanoate in good yield which is easily converted to cyclopentadecanolide (CPDL). In addition, the alkylation of acetone with 1,10-decanediol in the presence of [IrCl(cod)](2) and KOH resulted in an important muscone precursor, 2,15-hexadecanedione (HDDO), in good yield.