2-nonyn-1-ol-8,8,9,9-d4 | 196495-63-3

• 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: 2-nonyn-1-ol-8,8,9,9-d4
• CAS: 196495-63-3
• 化学式: C₉H₁₆O
• 分子量: 144.194
• InChiKey: XERDOEKKHDALKJ-LNLMKGTHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.95
• 重原子数：
  10.0
• 可旋转键数：
  5.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  2-nonyn-1-ol-8,8,9,9-d4 在 氨 、 lithium 作用下， 以 四氢呋喃 为溶剂， 反应 4.5h， 以88%的产率得到2-trans-nonen-1-ol-8,8,9,9-d4
  参考文献：
  名称：

  Preparation of methyl cis-9, trans-11- and trans-9, trans-11-octadecadienoate-17,17,18,18-d4, two of the isomers of conjugated linoleic acid

  摘要：

  A multi-step synthesis was used to prepare the cis-9, trans-11- and trans-9, trans-11-isomers (in a ratio of 46/54) of conjugated linoleic acid (cis-9, trans-11-octadecadienoic acid) labeled with deuterium atoms on the 17- and 18-carbon atoms (17,17,18,18-d(4)). The methyl cis/trans-9, trans-11-octadecadienoate-17,17,18,18-d(4) isomer pair were obtained from the Wittig coupling of trans-2-nonenyltriphenyl-phosphonium bromide (8,8,9,9-d(4)) and methyl 9-oxononanoate. To prepare the phosphonium bromide, 5-hexyn-1-ol was reduced with deuterium gas/Wilkinson's catalyst to yield 1-hexanol-5,5,6,6-d(4). The alcohol was converted to the iodide with phosphorous pentoxide/phosphoric acid/potassium iodide. Coupling of the iodide with 2-propyn-1-ol via lithium amide in liquid ammonia gave 2-nonyn-1-ol-d(4). The acetylenic alcohol was reduced with lithium metal in liquid ammonia to yield the trans-2-nonen-1-ol-d(4). The alcohol was converted to the bromide (using triphenylphosphine dibromide) and then converted to the phosphonium salt. The aldehyde ester was prepared by the reductive ozonization of methyl 9-cis-octadecenoate. The two conjugated linoleic acid isomers, formed during the final Wittig coupling reaction, were readily separated by a combination of reversed-phase and silver resin chromatography. Isotopic and chemical purities were > 95% for each geometric isomer. Overall yield (both isomers) from the 8-step synthesis was 12%. (C) 1997 Elsevier Science Ireland Ltd.

  DOI：

  10.1016/s0009-3084(97)00053-4
• 作为产物：
  描述：

  2-(5,5,6,6-tetradeutero-hexyloxy)tetrahydropyran 在 氨 、 phosphorus pentoxide 、 二氢四氧代磷酸 、 lithium 、 ferric nitrate 、 potassium iodide 作用下， 以 四氢呋喃 为溶剂， 反应 29.5h， 生成 2-nonyn-1-ol-8,8,9,9-d4
  参考文献：
  名称：

  Preparation of methyl cis-9, trans-11- and trans-9, trans-11-octadecadienoate-17,17,18,18-d4, two of the isomers of conjugated linoleic acid

  摘要：

  A multi-step synthesis was used to prepare the cis-9, trans-11- and trans-9, trans-11-isomers (in a ratio of 46/54) of conjugated linoleic acid (cis-9, trans-11-octadecadienoic acid) labeled with deuterium atoms on the 17- and 18-carbon atoms (17,17,18,18-d(4)). The methyl cis/trans-9, trans-11-octadecadienoate-17,17,18,18-d(4) isomer pair were obtained from the Wittig coupling of trans-2-nonenyltriphenyl-phosphonium bromide (8,8,9,9-d(4)) and methyl 9-oxononanoate. To prepare the phosphonium bromide, 5-hexyn-1-ol was reduced with deuterium gas/Wilkinson's catalyst to yield 1-hexanol-5,5,6,6-d(4). The alcohol was converted to the iodide with phosphorous pentoxide/phosphoric acid/potassium iodide. Coupling of the iodide with 2-propyn-1-ol via lithium amide in liquid ammonia gave 2-nonyn-1-ol-d(4). The acetylenic alcohol was reduced with lithium metal in liquid ammonia to yield the trans-2-nonen-1-ol-d(4). The alcohol was converted to the bromide (using triphenylphosphine dibromide) and then converted to the phosphonium salt. The aldehyde ester was prepared by the reductive ozonization of methyl 9-cis-octadecenoate. The two conjugated linoleic acid isomers, formed during the final Wittig coupling reaction, were readily separated by a combination of reversed-phase and silver resin chromatography. Isotopic and chemical purities were > 95% for each geometric isomer. Overall yield (both isomers) from the 8-step synthesis was 12%. (C) 1997 Elsevier Science Ireland Ltd.

  DOI：

  10.1016/s0009-3084(97)00053-4