methyl (R)-3-hydroxyeicosa-5,8,11,14-tetraynoate | 479070-42-3

• 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: methyl (R)-3-hydroxyeicosa-5,8,11,14-tetraynoate
• 英文别名: methyl (3R)-3-hydroxyicosa-5,8,11,14-tetraynoate
• CAS: 479070-42-3
• 化学式: C₂₁H₂₆O₃
• 分子量: 326.436
• InChiKey: PHLWARBHPFVRBZ-HXUWFJFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl (R)-3-hydroxyeicosa-5,8,11,14-tetraynoate 在 Lindlar's catalyst 喹啉 、 lithium hydroxide 、 氢气 作用下， 以 甲醇 、 苯 为溶剂， 反应 9.0h， 生成 (3R,5Z,8Z,11Z,14Z)-3-hydroxyeicosa-5,8,11,14-tetraenoic acid
  参考文献：
  名称：

  A novel synthesis of 3(R)-HETE, 3(R)-HTDE and enzymatic synthesis of 3(R),15(S)-DiHETE

  摘要：

  3(R)-HETE and 3(R)-HTDE were prepared by cross-coupling of methyl 3(R)-hydroxyhex-5-ynoate either with 1-bromo-2,5,8-tetradecatriyne or 1-bromo-2-octyne followed by catalytic hydrogenation of the skipped triple bonds formed using Lindlar's catalyst. Enzymatic synthesis of 3(R),15(S)-DiHETE was accomplished by soybean LOX-1 using 3(R)-HETE as a substrate. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01289-9
• 作为产物：
  描述：

  (3R)-3-hydroxy-5-hexynenitrile 在 sodium hydroxide 、 copper(l) iodide 、 potassium carbonate 、 sodium iodide 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 methyl (R)-3-hydroxyeicosa-5,8,11,14-tetraynoate
  参考文献：
  名称：

  A novel synthesis of 3(R)-HETE, 3(R)-HTDE and enzymatic synthesis of 3(R),15(S)-DiHETE

  摘要：

  3(R)-HETE and 3(R)-HTDE were prepared by cross-coupling of methyl 3(R)-hydroxyhex-5-ynoate either with 1-bromo-2,5,8-tetradecatriyne or 1-bromo-2-octyne followed by catalytic hydrogenation of the skipped triple bonds formed using Lindlar's catalyst. Enzymatic synthesis of 3(R),15(S)-DiHETE was accomplished by soybean LOX-1 using 3(R)-HETE as a substrate. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01289-9

文献信息

• Synthesis of tritium labelled 3(R)-HETE and 3(R),18(R/S)-DiHETE through a common synthetic route
  作者：Natalya V. Groza、Igor V. Ivanov、Stepan G. Romanov、Valery P. Shevchenko、Nikolai F. Myasoedov、Santosh Nigam、Galina I. Myagkova

  DOI：10.1002/jlcr.791

  日期：2004.1

  An efficient procedure for the synthesis of 3-hydroxyoxylipins labelled with tritium on all double bond positions is reported. The synthetic scheme involves a joint route for the formation of tetraacetylenic precursors followed by stereoselective reduction of the triple bonds either with hydrogen or tritium. The final tritiated products were obtained with specific activities ranging from 1.65 to 1.80 Ci/mmol. Copyright © 2003 John Wiley & Sons, Ltd.

  本报告介绍了一种在所有双键位置上用氚标记的 3-hydroxyoxylipins 的高效合成程序。该合成方案包括四乙炔前体的联合生成路线，然后用氢或氚对三键进行立体选择性还原。最终得到的氚化产物的比活度为 1.65 至 1.80 Ci/mmol。Copyright © 2003 John Wiley & Sons, Ltd. All Rights Reserved.
• A novel synthesis of 3(R)-HETE, 3(R)-HTDE and enzymatic synthesis of 3(R),15(S)-DiHETE
  作者：Natalia V Groza、Igor V Ivanov、Stepan G Romanov、Galina I Myagkova、Santosh Nigam

  DOI：10.1016/s0040-4020(02)01289-9

  日期：2002.12

  3(R)-HETE and 3(R)-HTDE were prepared by cross-coupling of methyl 3(R)-hydroxyhex-5-ynoate either with 1-bromo-2,5,8-tetradecatriyne or 1-bromo-2-octyne followed by catalytic hydrogenation of the skipped triple bonds formed using Lindlar's catalyst. Enzymatic synthesis of 3(R),15(S)-DiHETE was accomplished by soybean LOX-1 using 3(R)-HETE as a substrate. (C) 2002 Elsevier Science Ltd. All rights reserved.