rac-3-(benzoyloxy)-14-bromotetradeca-6,9,12-triyne | 478688-29-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: rac-3-(benzoyloxy)-14-bromotetradeca-6,9,12-triyne
• 英文别名: 3-(benzyloxy)-14-bromotetradeca-6,9,12-triyne；14-Bromotetradeca-6,9,12-triyn-3-yl benzoate
• CAS: 478688-29-8
• 化学式: C₂₁H₂₁BrO₂
• 分子量: 385.301
• InChiKey: QDYOMBPAXWRHCG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 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：

  rac-3-(benzoyloxy)-14-bromotetradeca-6,9,12-triyne 在 喹啉 、 sodium hydroxide 、 copper(l) iodide 、 氢气 、 potassium carbonate 、 sodium iodide 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 1.0h， 生成 18-hydroxyeicosatetraenoic acid
  参考文献：
  名称：

  Total synthesis of (5Z,8Z,11Z,14Z)-18- and 19-oxoeicosa-5,8,11,14-tetraenoic acids

  摘要：

  8-oxo-ETE was synthesized via the corresponding tetraacetylenic precursor, which was prepared by cross-coupling of three key synthons: methyl 5-hexynoate, the bisfunctional C-7-C-13 fragment-7-bromo-2,5-heptadiyne-l-ol and rac-3-(benzoyloxy)hept-6-yn. The carbonyl function was introduced at the last synthesis step. 19-oxo-ETE was synthesized by coupling of acid anhydride, prepared from monomethyl ester of(5Z,8Z,l IZ,14Z)-nonadeca-5,8,11,14-tetraen-1,19-dioic acid, either with lithium dimethylcuprate or methylcuprate in a one-step procedure. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01029-3
• 作为产物：
  描述：

  1-氯-3-戊醇 在 吡啶 、 copper(l) iodide 、 正丁基锂 、 四溴化碳 、 四丁基氟化铵 、 potassium carbonate 、 三苯基膦 、 sodium iodide 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 、 苯 为溶剂， 反应 46.58h， 生成 rac-3-(benzoyloxy)-14-bromotetradeca-6,9,12-triyne
  参考文献：
  名称：

  Total synthesis of (5Z,8Z,11Z,14Z)-18- and 19-oxoeicosa-5,8,11,14-tetraenoic acids

  摘要：

  8-oxo-ETE was synthesized via the corresponding tetraacetylenic precursor, which was prepared by cross-coupling of three key synthons: methyl 5-hexynoate, the bisfunctional C-7-C-13 fragment-7-bromo-2,5-heptadiyne-l-ol and rac-3-(benzoyloxy)hept-6-yn. The carbonyl function was introduced at the last synthesis step. 19-oxo-ETE was synthesized by coupling of acid anhydride, prepared from monomethyl ester of(5Z,8Z,l IZ,14Z)-nonadeca-5,8,11,14-tetraen-1,19-dioic acid, either with lithium dimethylcuprate or methylcuprate in a one-step procedure. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01029-3

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.
• Total synthesis of (5Z,8Z,11Z,14Z)-18- and 19-oxoeicosa-5,8,11,14-tetraenoic acids
  作者：Stepan G Romanov、Igor V Ivanov、Nataliya V Groza、Hartmut Kuhn、Galina I Myagkova

  DOI：10.1016/s0040-4020(02)01029-3

  日期：2002.10

  8-oxo-ETE was synthesized via the corresponding tetraacetylenic precursor, which was prepared by cross-coupling of three key synthons: methyl 5-hexynoate, the bisfunctional C-7-C-13 fragment-7-bromo-2,5-heptadiyne-l-ol and rac-3-(benzoyloxy)hept-6-yn. The carbonyl function was introduced at the last synthesis step. 19-oxo-ETE was synthesized by coupling of acid anhydride, prepared from monomethyl ester of(5Z,8Z,l IZ,14Z)-nonadeca-5,8,11,14-tetraen-1,19-dioic acid, either with lithium dimethylcuprate or methylcuprate in a one-step procedure. (C) 2002 Elsevier Science Ltd. All rights reserved.