2-benzyloxypent-4-yne | 75405-49-1

• 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: 2-benzyloxypent-4-yne
• 英文别名: 4-benzyloxy-1-pentyne；Benzene, [[(1-methyl-3-butynyl)oxy]methyl]-；pent-4-yn-2-yloxymethylbenzene
• CAS: 75405-49-1
• 化学式: C₁₂H₁₄O
• 分子量: 174.243
• InChiKey: UKSXFTBAIZKREV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-benzyloxypent-4-yne 在 palladium on activated charcoal 正丁基锂 、 氢气 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， -78.0~20.0 ℃ 、101.33 kPa 条件下， 反应 15.0h， 生成 (5R,7R)-7-Methyl-1,6-dioxaspiro<4.5>decane
  参考文献：
  名称：

  Alkynyltrifluoroborates as Versatile Tools in Organic Synthesis:  A New Route to Spiroketals

  摘要：

  A simple and efficient two-step approach to spiroketals is described. Key steps include the preparation of functionalized hydroxyl alpha-alkynones by ring-opening reactions of lactones with lithium alkynyltrifluoroborates followed by a palladium-catalyzed hydrogenation/spirocyclization of the prespiroketal intermediate.

  DOI：

  10.1021/ol047987k
• 作为产物：
  描述：

  4-戊炔-2-醇 、 溴甲苯 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以83%的产率得到2-benzyloxypent-4-yne
  参考文献：
  名称：

  Volatile organic compounds produced by the phytopathogenic bacterium Xanthomonas campestris pv. vesicatoria 85-10

  摘要：

  Xanthomonas campestris是一种植物病原细菌，引起许多与农业相关的疾病。挥发物被证明在跨和内部有机体的吸引和防御反应中起重要作用。最近，人们意识到细菌也会释放大量挥发物，影响其他生物，如无脊椎动物、植物和真菌。为了研究基于挥发物的细菌-植物相互作用的第一步，利用GC/MS和PTR-MS技术确定了Xanthomonas c. pv. vesicatoria 85-10的排放谱。该物种排放了50多种化合物，其中大部分是酮和甲基酮。通过GC/MS获得的分析数据确定了主要化合物10-甲基十一烷-2-酮的结构，并通过与合成参考样品的数据进行比较进行了验证。在双部分培养皿生物测定中，商业可获得的癸酮、十一酮、十二酮以及新合成的10-甲基十一烷-2-酮在低浓度（0.01至10μmol）下促进了生长，而100μmol的癸酮抑制了真菌Rhizoctonia solani的生长。细菌在含葡萄糖和不含葡萄糖的培养基（营养琼脂）上生长时的挥发物排放谱不同。

  DOI：

  10.3762/bjoc.8.65

文献信息

• Process for the preparation of azidoperfluoroalkanes and N-polyfluoroalkyl azides
  申请人：Ustav organicke chemie a biochemie AV CR, v.v.i.

  公开号：US20190161452A1

  公开（公告）日：2019-05-30

  Process for the preparation of azidoperfluoroalkanes and azidopolyfluoroalkanes of general formula R F —N 3 , where R F is chosen from a group containing C n F 2n+1 , C n F x H 2n+1−x , C n F x X 2n+1−x or R 1 CF 2 CF 2 , where n is an integer in the range of 1 to 10, x is an integer in the range of 2 to 20, X is Cl, Br, or I, R 1 is C 1-10 alkyl, ArO, ArS, imidazolyl, benzimidazolyl, or pyrazolyl and Ar is phenyl or substituted phenyl, by the reaction of electrophilic azidation reagent of general formula R 2 —N 3 , where R 2 is n-C 4 F 9 SO 2 , ArSO 2 , Br, I, with synthetic equivalent of polyfluoroalkylated carbanion of general formula [R F ] − .

  通用公式RF—N3的叠氮全氟烷和叠氮多氟烷的制备过程，其中RF选择自包含CnF2n+1、CnFxH2n+1−x、CnFxX2n+1−x或R1CF2CF2的一组化合物，其中n为1至10范围内的整数，x为2至20范围内的整数，X为Cl、Br或I，R1为C1-10烷基、ArO、ArS、咪唑基、苯并咪唑基或吡唑基，Ar为苯基或取代苯基，通过亲电性叠氮试剂R2—N3的反应，其中R2为n-C4F9SO2、ArSO2、Br、I的通用公式，与通用公式[RF]−的多氟烷基化碳负离子的合成等效物的反应。
• Process for preparing tertiary alkynols
  申请人：Loyola University of Chicago

  公开号：US05349071A1

  公开（公告）日：1994-09-20

  Processes for synthesizing tertiary alkynols by reacting carbonyl-group-containing compounds with alkynes in the presence of a basic catalyst are disclosed. Preferred products are 6,10,14-trimethyl-4-pentadecyn-6-ol compounds having the structure: ##STR1## A preferred, novel compound, 6,10,14-trimethyl-4-pentadecyne-2,6-diol, can be used in the synthesis of Vitamin E or Vitamin K.sub.1.

  揭示了在碱性催化剂存在下，通过将含羰基化合物与炔烃反应合成三级炔醇的过程。首选产品是具有以下结构的6,10,14-三甲基-4-戊烯基-6-醇化合物：##STR1## 一种首选的新型化合物，6,10,14-三甲基-4-戊炔基-2,6-二醇，可用于合成维生素E或维生素K.sub.1。
• Highly Stereoselective and Efficient Hydrosilylation of Terminal Alkynes Catalyzed by [RuCl₂(<i>p</i>-cymene)]₂
  作者：Youngim Na、Sukbok Chang

  DOI：10.1021/ol0059697

  日期：2000.6.1

  [RuCl(2)(p-cymene)](2) as a catalyst, extremely high regio- and stereoselectivity was observed in the hydrosilylation reaction of various terminal alkynes under mild conditions to afford beta-(Z)-vinylsilanes in excellent yields. A dramatic directing effect was also observed when alkynes having a hydroxyl group at the beta position to the triple bond were employed as a substrate, and in these cases regioisomeric

  以[RuCl（2）（p-cymene）]（2）作为催化剂，在温和条件下，各种末端炔烃的氢化硅烷化反应中观察到极高的区域选择性和立体选择性，从而以极高的收率得到β-（Z）-乙烯基硅烷。当使用在三键的β位具有羟基的炔烃作为底物时，也观察到了引人注目的指导作用，在这些情况下，以优异的选择性产生了区域异构的α-乙烯基硅烷。
• Sphingosine-1-phosphate receptor agonist and antagonist compounds
  申请人：Wallace Grier A.

  公开号：US20090029947A1

  公开（公告）日：2009-01-29

  The present invention is directed to novel, potent, and selective agents, which are agonists or antagonists of the one or more of the individual receptors of the S1P receptor family. The compounds of the invention are useful as therapeutics for treating medical conditions associated with agonism or antagonism of the individual receptors of the S1P receptor family.

  本发明涉及一种新型、有效和选择性的药剂，它们是S1P受体家族中一个或多个单个受体的激动剂或拮抗剂。本发明的化合物可用作治疗与S1P受体家族中单个受体的激动或拮抗有关的医学状况的治疗剂。
• ——
  作者：Regine Gries、Grigori Khaskin、Gerhard Gries、Robb G. Bennett、G. G. Skip King、Petra Morewood、Keith N. Slessor、W. Dean Morewood

  DOI：10.1023/a:1021005517389

  日期：——

  Our objectives were to identify and field test the sex pheromone of female Douglas-fir cone gall midge, Contarinia oregonensis (Diptera: Cecidomyiidae). Coupled gas chromatographic-electroantennographic detection (GC-EAD) analyses of pheromone extract revealed a single compound (A) that elicited responses from male antennae. Hydrogenation of pheromone extract, followed by renewed GC-EAD analysis, revealed a new EAD-active compound with chromatographic characteristics identical to those of tridecan-2-yl acetate on five fused silica columns (DB-5, DB-210, DB-23, SP-1000, and Cyclodex-B). Syntheses, chromatography, and retention index calculations of all possible tridecen-2-yl acetates suggested that the candidate pheromone A was a tridecadien-2-yl acetate with nonconjugated double bonds. Synthetic candidate pheromone component (Z,Z)-4,7-tridecadien-2-yl acetate (Z4Z7) cochromatographed with A on all analytical columns and elicited comparable antennal activity. In GC-EAD analyses that separated the enantiomers (Z,Z)4,7-tridecadien-(S)-2-yl acetate (2S-Z4Z7) and (Z,Z)-4,7-tridecadien-(R)-2-yl acetate (2R-Z4Z7) with baseline resolution, only 2S-Z4Z7 as a component in a racemic standard or in pheromone extract elicited antennal responses. In Douglas-fir seed orchards, sticky traps baited with 2S-Z4Z7 captured male C. oregonensis, whereas 2R-Z4Z7 was behaviorally benign. Comparable catches of males in traps baited with racemic Z4Z7 (50 mug) or virgin female C. oregonensis suggested that synthetic pheromone baits could be developed for monitoring C. oregonensis populations in commercial Douglas-fir seed orchards.