(2E)-11-<(tetrahydro-2H-pyran-2-yl)oxy>-undec-2-en-1-ol | 76387-42-3

• 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: (2E)-11-<(tetrahydro-2H-pyran-2-yl)oxy>-undec-2-en-1-ol
• 英文别名: 11-Tetrahydropyranyloxyundec-2(E)-en-1-ol；11-(tetrahydro-2-pyranyloxy)-(E)-undec-2-en-1-ol；11-(tetrahydropyran-2-yloxy)-undec-2-en-1-ol；(E)-11-(oxan-2-yloxy)undec-2-en-1-ol
• CAS: 76387-42-3
• 化学式: C₁₆H₃₀O₃
• 分子量: 270.412
• InChiKey: HTGJZAGCNCCAGL-RMKNXTFCSA-N

物化性质

• 沸点：
  397.5±42.0 °C(Predicted)
• 密度：
  0.97±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  19
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2E)-11-<(tetrahydro-2H-pyran-2-yl)oxy>-undec-2-en-1-ol 在 吡啶 、 4-甲基苯磺酸吡啶 、 copper(II) iodide 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 8.67h， 生成 (E)-9-十二碳烯-1-醇乙酸酯
  参考文献：
  名称：

  Vig, O. P.; Sharma, M. L.; Verma, N. K., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1980, vol. 19, # 8, p. 692 - 694

  摘要：

  DOI：
• 作为产物：
  描述：

  1-溴-8-(四氢吡喃氧基)辛烷 在 lithium aluminium tetrahydride 、 lithium amide 、 氨 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 为溶剂， 反应 15.0h， 生成 (2E)-11-<(tetrahydro-2H-pyran-2-yl)oxy>-undec-2-en-1-ol
  参考文献：
  名称：

  光学活性金刚烷酰胺的首次合成

  摘要：

  开发了一种通用的立体选择性方法，用于光学活性氮杂马来酰亚胺的首次合成。

  DOI：

  10.1016/0040-4039(96)01960-0

文献信息

• First synthesis of optically active azamacrolides
  作者：B Venkateswara Rao、V Satish Kumar、M Nagarajan、D Sitaramaiah、AV Rama Rao

  DOI：10.1016/0040-4039(96)01960-0

  日期：1996.11

  A common stereoselective approach was developed for the first synthesis of optically active azamacrolides.

  开发了一种通用的立体选择性方法，用于光学活性氮杂马来酰亚胺的首次合成。
• Identification, Syntheses, and Characterization of the Geometric Isomers of 9,11-Hexadecadienal from Female Pheromone Glands of the Sugar Cane Borer <i>Diatraea saccharalis</i>
  作者：Ellen M. Santangelo、Myrian Coracini、Peter Witzgall、Arlene G. Correa、C. Rikard Unelius

  DOI：10.1021/np010551i

  日期：2002.6.1

  Chemical analysis of the pheromone glands of the sugar cane borer Diatraea saccharalis has shown the presence of the four geometric isomers of 9,11-hexadecadienal (1-4), in addition to hexadecanal and (Z)-hexadec-11-enal. We here report the syntheses and characterization of compounds 1-4. One starting material, 9-decen-1-ol, has been used to obtain all of them via divergent synthetic routes.

  对甘蔗蛀虫Diatraea saccharalis的信息素腺的化学分析表明，除了十六烷醛和（Z）-hexadec-11-enal之外，还存在9,11-十六二烯醛（1-4）的四种几何异构体。我们在这里报告了化合物1-4的合成与表征。一种原料9-癸烯-1-醇已用于通过不同的合成途径获得所有这些原料。
• A 13-Oxo-9,10-epoxytridecenoate Phospholipid Analogue of the Genotoxic 4,5-Epoxy-2<i>E</i>-decenal: Detection in Vivo, Chemical Synthesis, and Adduction with DNA
  作者：Clementina Mesaros、Bogdan G. Gugiu、Rong Zhou、Seon Hwa Lee、Jaewoo Choi、James Laird、Ian A. Blair、Robert G. Salomon

  DOI：10.1021/tx9002484

  日期：2010.3.15

  Often guided by analogy with nonphospholipid products from oxidative cleavage of polyunsaturated fatty acids, we previously identified a variety of biologically active oxidatively truncated phospholipids. Previously, 4,5-epoxy-2(E)-decenal (4,5-EDE) was found to be produced by oxidative cleavage of 13(S)-hydroperoxy-9,11-(Z,E)-octadeca-dienoic acid (13-HPODE). 4,5-EDE reacts with deoxy-adenosine (dAdo) and deoxy-guanosine (dGuo) to form mutagenic etheno derivatives. We hypothesized that a functionally similar and potentially mutagenic compound, that is, 13-oxo-9,10-epoxytridecenoic acid (OETA), would be generated from 9-HPODE through an analogous fragmentation. We expected that an ester of 2-lysophosphatidylcoline (PC), OETA-PC, would be produced by oxidative cleavage of 9-HPODE-PC in biological membranes. An efficient, unambiguous total synthesis of traps-OETA-PC was first executed to provide a standard that could facilitate the identification of this phospholipid epoxyalkenal that was shown to be produced during oxidation of the linoleic acid ester of 2-lysoPC. Finally, trans-OETA-PC was detected in a lipid extract from rat retina. The identity of the naturally occurring oxidatively truncated phospholipid was further confirmed by derivatization with methoxylamine that produced characteristic mono and bis adducts. The average amount of traps-OETA-PC in rat retina, 0.33 pmol, is relatively low as compared to other oxidatively truncated PCs, for example, the 4-hydroxy-7-oxohept-5-enoic acid PC ester (2.5 pmol) or the 4-keto-7-oxohept-5-enoic acid PC ester (1.7 pmol), derived from the docosahexaenoic acid ester of 2-lysoPC. This, most likely, is because docosahexaenoate PCs are particularly abundant in the retina as compared to the linoleate PC ester precursor of OETA-PC. As predicted by analogy with 4,5-EDE, OETA-PC reacts with dAdo and dGuo, as well as with DNA, to form mutagenic etheno adducts.
• Sex attractant pheromone of the pecan nut casebearer (Lepidoptera: Pyralidae)
  作者：Jocelyn G. Millar、Allen E. Knudson、J.Steven McElfresh、Regine Gries、Gerhard Gries、James H. Davis

  DOI：10.1016/0968-0896(96)00010-7

  日期：1996.3

  A female-produced sex pheromone for the pecan nut casebearer, Acrobasis nuxvorella Neunzig, has been identified from pheromone gland extracts of calling female moths. The compound (9E,11Z)-hexadecadienal [(9E,11Z)-16:Ald] was identified by coupled GC-EAD and retention time matches with a synthetic standard on four capillary GC columns of different polarities. Corroboration of the identification of (9E, 11Z)-16:Ald by other analytical chemistry methods was not possible due to the minute quantities of pheromone extracted (<1 picogram/female). In field studies, gray rubber septa impregnated with 100 mu g of synthetic (9E,11Z)-16:Ald were attractive to male moths, whereas higher and lower doses were less attractive. The homologous (9E,11Z)-15:Ald was also slightly attractive, while the more highly conjugated analogues, (9E,11Z,13Z)- and (9E, 11Z,13E)-16:Ald, were not. Copyright (C) 1996 Elsevier Science Ltd
• Ochiai, Masahito; Ukita, Tatsuzo; Fujita, Eiichi, Chemical and pharmaceutical bulletin, 1983, vol. 31, # 5, p. 1641 - 1645
  作者：Ochiai, Masahito、Ukita, Tatsuzo、Fujita, Eiichi

  DOI：——

  日期：——