2-Decyl-1-ol THP ether | 88517-98-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: 2-Decyl-1-ol THP ether
• 英文别名: 2-decynyltetrahydro-2H-pyran-2-yl ether；2-[(Dec-2-yn-1-yl)oxy]oxane；2-dec-2-ynoxyoxane
• CAS: 88517-98-0
• 化学式: C₁₅H₂₆O₂
• 分子量: 238.37
• InChiKey: NSZSQEWGSFAPIE-UHFFFAOYSA-N

物化性质

• 沸点：
  349.1±32.0 °C(Predicted)
• 密度：
  0.93±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-Decyl-1-ol THP ether 在 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 生成 2-癸炔-1-醇
  参考文献：
  名称：

  Titanium(II)-based Z-reduction of alkynes. Syntheses of deuterium labelled linolenic and oleic acids and (3E,8Z,11Z )-tetradeca-3,8,11-trienyl acetate, the sex pheromone of a tomato pest, Scrobipalpuloides absoluta

  摘要：

  本文描述了一种操作简便的TiII介导的一锅法立体和区域选择性还原孤立共轭亚甲基跳跃多炔烃至相应的Z-多烯烃的方法，并应用于氘标记亚麻酸和油酸的合成。最终用D2O（而非H2O）淬灭反应，实现了炔烃的区域和立体选择性双氘化。(3E,8Z,11Z)-十四碳-3,8,11-三烯基乙酸酯（主要性信息素）和(3Z,8Z,11Z)异构体的合成，利用了这种方法在关键还原步骤中，且不足或过度还原的情况可忽略不计。

  DOI：

  10.1039/a800674a
• 作为产物：
  描述：

  3,4-二氢-2H-吡喃 在 正丁基锂 、 对甲苯磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 2-Decyl-1-ol THP ether
  参考文献：
  名称：

  Titanium(II)-based Z-reduction of alkynes. Syntheses of deuterium labelled linolenic and oleic acids and (3E,8Z,11Z )-tetradeca-3,8,11-trienyl acetate, the sex pheromone of a tomato pest, Scrobipalpuloides absoluta

  摘要：

  本文描述了一种操作简便的TiII介导的一锅法立体和区域选择性还原孤立共轭亚甲基跳跃多炔烃至相应的Z-多烯烃的方法，并应用于氘标记亚麻酸和油酸的合成。最终用D2O（而非H2O）淬灭反应，实现了炔烃的区域和立体选择性双氘化。(3E,8Z,11Z)-十四碳-3,8,11-三烯基乙酸酯（主要性信息素）和(3Z,8Z,11Z)异构体的合成，利用了这种方法在关键还原步骤中，且不足或过度还原的情况可忽略不计。

  DOI：

  10.1039/a800674a

文献信息

• Titanium(II)-based Z-reduction of alkynes. Syntheses of deuterium labelled linolenic and oleic acids and (3E,8Z,11Z )-tetradeca-3,8,11-trienyl acetate, the sex pheromone of a tomato pest, Scrobipalpuloides absoluta
  作者：Natasha L. Hungerford、William Kitching

  DOI：10.1039/a800674a

  日期：——

  An operationally simple TiII-mediated, stereo- and regio-specific reduction of isolated, conjugated and methylene ‘skipped’ polyynes to the corresponding Z-polyenes in a one-pot procedure is described and applied inter alia to the syntheses of deuterium labelled linolenic and oleic acids. Final quenching with D2O (instead of H2O) results in regio- and stereo-specific Z-dideuteration of the alkyne. The synthesis of (3E,8Z,11Z)-tetradeca-3,8,11-trienyl acetate, the major sex pheromone of Scrobipalpuloides absoluta, a destructive pest of tomatoes, and the (3Z,8Z,11Z)-isomer, utilises this methodology in key reduction steps, and under- or over-reduction are negligible.

  本文描述了一种操作简便的TiII介导的一锅法立体和区域选择性还原孤立共轭亚甲基跳跃多炔烃至相应的Z-多烯烃的方法，并应用于氘标记亚麻酸和油酸的合成。最终用D2O（而非H2O）淬灭反应，实现了炔烃的区域和立体选择性双氘化。(3E,8Z,11Z)-十四碳-3,8,11-三烯基乙酸酯（主要性信息素）和(3Z,8Z,11Z)异构体的合成，利用了这种方法在关键还原步骤中，且不足或过度还原的情况可忽略不计。
• [DE] 2-HEPTYLCYCLOPROPYL-1-CARBONSÄURE<br/>[EN] 2-HEPTYLCYCLOPROPYL-1-CARBOXYLIC ACID<br/>[FR] ACIDE 2-HEPTYLCYCLOPROPYL-1-CARBOXYLIQUE
  申请人：SYMRISE GMBH & CO KG

  公开号：WO2004046079A1

  公开（公告）日：2004-06-03

  Offenbart werden gegebenenfalls isolierte und/oder aufgereinigte Enantiomere der 2-Heptylcyclopropyl-1-carbonsäure sowie Gemische von zwei, drei oder sämtlichen Enantiomeren der 2-Heptylcyclopropyl-1 carbonsäure als Duft­-und/oder Aromastoffe.

  必要时，2-庚基环丙基-1-羧酸的孤立和/或纯化对映体可能会被揭示，以及2-庚基环丙基-1-羧酸的两个、三个或所有对映体的混合物作为香料和/或香精。
• (Carboxyalkyl)benzyl Propargyl Ethers as Selective Inhibitors of Leukocyte-Type 12-Lipoxygenases
  作者：Gilles Gorins、Lethea Kuhnert、Carl R. Johnson、Lawrence J. Marnett

  DOI：10.1021/jm9606047

  日期：1996.1.1

  A series of (carboxyalkyl)benzyl propargyl ethers was synthesized and tested as inhibitors of 12-lipoxygenase (12-LO) from porcine leukocyte cytosol. Optimum activity was displayed by 3-[4-[(2-tridecynyloxy)methyl]phenyl]propanoic acid. Altering the length of the alkyl side chain attached to the acetylenic group reduced activity. Changing the substitution pattern in the (carboxyalkyl)benzyl group from para to meta or ortho also reduced activity. Analogs in which the triple bond was replaced by a double bond or an allene displayed reduced activity, whereas fully saturated analogs were inactive. High concentrations (10 mu M) of the most potent acetylenic (carboxylalkyl)benzyl ethers did not inhibit human platelet 12-LO, human neutrophil 5-LO, rabbit reticulocyte 15-LO, or soybean 15-LO. Thus, this class of compounds represents the first example of isoform specific LO inhibitors.
• Sex attractants of geometrid and noctuid moths: Chemical characterization and field test of monoepoxides of 6,9-dienes and related compounds
  作者：Tetsu Ando、Hideki Kishi、Naoko Akashio、Xu-Rong Qin、Namiko Saito、Hiroshi Abe、Satoshi Hashimoto

  DOI：10.1007/bf02036719

  日期：1995.3

  (Z,Z)-6,9-Dienes with straight C-18-C-23 chains were synthesized from linoleic acid, and a C-17 chain was synthesized by hydrogenation of the corresponding 6,9-diyne prepared from propargyl alcohol. Oxidation of the homoconjugated dienes with m-chloroperoxybenzoic acid yielded a 1:1 mixture of two monoepoxides that could be separated by repeated medium-pressure liquid chromatography with a Lobar column. The chemical structure of each positional isomer was confirmed by analyses of the ozonolysis products, and the isomers showed characteristic C-13 signals in their NMR spectra and fragment ions in their EI mass spectra. In addition to the (Z,Z,Z)-3,6,9-trienes with straight C-18-C-23 chains and their monoepoxides, field tests using single source lures incorporating one of the above seven dienes and 14 monoepoxymonoenes were carried out in a forest in Tokyo from 1992 to 1994. Consequently, attraction of six geometrid species and five noctuid species was observed for the first time.
• US7754675B2
  申请人：——

  公开号：US7754675B2

  公开（公告）日：2010-07-13