cis-ximenynic acid methyl ester | 198474-00-9

• 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: cis-ximenynic acid methyl ester
• 英文别名: methyl octadec-11Z-en-9-ynoate；octadec-11c-en-9-ynoic acid methyl ester；Octadec-11c-en-9-insaeure-methylester；Methyl octadec-11 z-en-9-ynoate；methyl (Z)-octadec-11-en-9-ynoate
• CAS: 198474-00-9
• 化学式: C₁₉H₃₂O₂
• 分子量: 292.462
• InChiKey: QMZUILXAAOEXNR-HJWRWDBZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  21
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  cis-ximenynic acid methyl ester 在 硫酸 、 溶剂黄146 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 methyl 11,12-dihydroxy-octadec-9-ynoate
  参考文献：
  名称：

  Novel azido fatty acid ester derivatives from conjugated C18 enynoate

  摘要：

  Methyl octadec-11 Z-en-9-ynoate(1) was epoxidized to give methyl 11,12-Z-epoxy-octadec-9-ynoate (2, 81%). Acid catalyzed ring opening of the epoxy ring of compound 2 gave methyl 1 11,12-dihydroxy-octadec-9-ynoate (3, 80%). The latter was treated with mesyl chloride to yield methyl 11,12-dimesyloxy-octadec-9-ynoate (4, 76%). Reaction of compound 4 with sodium azide furnished methyl 11-azido-12-mesyloxy-octadec-9-ynoate (5a, 49%) and methyl 11-azido-octadec-11E-en-9-ynoate (5b, 24%). Compound 2 was semi-hydrogenated over Lindlar catalyst to give methyl 11,12-Z-epoxy-octadec-9Z-enoate (6, 90%). This allylic epoxy fatty ester (6) was reacted with sodium azide to give a mixture of methyl 11-azido-12-hydroxy-octadec-9Z-enoate (7a) and methyl 9-azido-12-hydroxy-octadec-9E-enoate (7b), which could not be separated into individual components by silica chromatography. Chromic acid oxidation of the mixture of compounds 7a and 7b furnished methyl 9-azido-12-oso-octadec-10E-enoate (8, 41% based on amount of compound 6 used) and an intractable mixture of polar compounds. The various products were characterized by NMR spectroscopic and mass spectral analyses. (C) 2001 Elsevier Science Ireland Ltd. All rights reserved.

  DOI：

  10.1016/s0009-3084(01)00140-2
• 作为产物：
  描述：

  (Z)-3-癸烯-1-炔 在 氨 、 sodium amide 、 丙酮 、 sodium iodide 作用下， 生成 cis-ximenynic acid methyl ester
  参考文献：
  名称：

  897.血脂。第七部分 8-羟基十八烷基顺式-11-和反式-11-en-9-炔诺酸的合成：天然8-羟甲磺酸的状态

  摘要：

  DOI：

  10.1039/jr9580004435

文献信息

• Separation and identification of ximenynic acid isomers in the seed oil of<i>Santalum spicatum</i> R.Br. as their 4,4‐dimethyloxazoline derivatives
  作者：Yandi D. Liu、Robert B. Longmore、John E. D. Fox

  DOI：10.1007/bf02517979

  日期：1996.12

  The seed oil ofSantalum spicatum contains a significant amount of ximenynic acid,trans‐11‐octadecen‐9‐ynoic acid, a long‐chain acetylenic fatty acid, as a major component (34%). The identity oftrans‐ximenynic acid was confirmed after isolation by ultraviolet, infrared, and nuclear magnetic resonance (NMR) (¹H‐ and¹³C‐) spectroscopy and by gas chromatography/mass spectrometry (GC/MS). Thecis isomer of ximenynic acid was also found (<1%) in some samples. Thecis andtrans isomers were characterized by GC/MS comparison of their methyl esters and 4,4‐dimethyloxazoline derivatives.

  摘要刺五加的种子油中含有大量的西门宁酸（反式-11-十八烯-9-炔酸），这是一种长链乙炔脂肪酸，是其主要成分（34%）。经紫外线、红外线和核磁共振（NMR）（1H- 和 13C-）光谱以及气相色谱/质谱法（GC/MS）分离后，确认了反式-西门宁酸的身份。在一些样品中还发现了西门酸的顺式异构体（<1%）。通过对其甲酯和 4,4-二甲基噁唑啉衍生物进行气相色谱/质谱比较，确定了顺式和反式异构体的特征。
• 897. Lipids. Part VII. Synthesis of 8-hydroxyoctadec-cis-11- and-trans-11-en-9-ynoic acid: the status of natural 8-hydroxyximenynic acid
  作者：L. Crombie、B. P. Griffin

  DOI：10.1039/jr9580004435

  日期：——
• Novel azido fatty acid ester derivatives from conjugated C18 enynoate
  作者：M.S.F. Lie Ken Jie、M.S. Alam

  DOI：10.1016/s0009-3084(01)00140-2

  日期：2001.5

  Methyl octadec-11 Z-en-9-ynoate(1) was epoxidized to give methyl 11,12-Z-epoxy-octadec-9-ynoate (2, 81%). Acid catalyzed ring opening of the epoxy ring of compound 2 gave methyl 1 11,12-dihydroxy-octadec-9-ynoate (3, 80%). The latter was treated with mesyl chloride to yield methyl 11,12-dimesyloxy-octadec-9-ynoate (4, 76%). Reaction of compound 4 with sodium azide furnished methyl 11-azido-12-mesyloxy-octadec-9-ynoate (5a, 49%) and methyl 11-azido-octadec-11E-en-9-ynoate (5b, 24%). Compound 2 was semi-hydrogenated over Lindlar catalyst to give methyl 11,12-Z-epoxy-octadec-9Z-enoate (6, 90%). This allylic epoxy fatty ester (6) was reacted with sodium azide to give a mixture of methyl 11-azido-12-hydroxy-octadec-9Z-enoate (7a) and methyl 9-azido-12-hydroxy-octadec-9E-enoate (7b), which could not be separated into individual components by silica chromatography. Chromic acid oxidation of the mixture of compounds 7a and 7b furnished methyl 9-azido-12-oso-octadec-10E-enoate (8, 41% based on amount of compound 6 used) and an intractable mixture of polar compounds. The various products were characterized by NMR spectroscopic and mass spectral analyses. (C) 2001 Elsevier Science Ireland Ltd. All rights reserved.