pent-2-yn-1-yl 4-methylbenzenesulfonate | 92666-05-2

• 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: pent-2-yn-1-yl 4-methylbenzenesulfonate
• 英文别名: 1-(p-Tosyloxy)-2-pentyne；pent-2-ynyl 4-methylbenzenesulfonate
• CAS: 92666-05-2
• 化学式: C₁₂H₁₄O₃S
• 分子量: 238.307
• InChiKey: VLHQNZIPSBLCKM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2905290000

反应信息

• 作为反应物：
  描述：

  pent-2-yn-1-yl 4-methylbenzenesulfonate 在 喹啉 、 乙基溴化镁 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (4Z,7Z)-4,7-decadien-1-yl acetate
  参考文献：
  名称：

  Identification of the sex pheromone of the lesser date moth, Batrachedra amydraula, using sequential SPME auto-sampling

  摘要：

  The identification of the sex pheromone of the lesser date moth, Batrachedra amydraula (Meyrick) was based on GC-MS analysis of volatiles released by virgin females using sequential SPME auto-sampling of headspace and by synthesis of the key component, (4Z,7Z)-4,7-decadien-1-yl acetate. Substantial capture of males in a date palm plantation using a bait consisting of the key component and 5Z-decen-1-yl acetate in a ratio of 1:2 indicated that these are the essential components of the sex pheromone. Addition of 4Z-decen-1-yl acetate and decan-1-yl acetate, which were also identified, did not affect trap-capture. The lesser date moth is the first member of the Batrachedridae whose sex pheromone has been identified. (4Z,7Z)-4,7-Decadien-1-yl acetate is a novel compound among moth sex pheromones. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.06.091
• 作为产物：
  描述：

  2-戊炔-1-醇 、 对甲苯磺酰氯 在 potassium hydroxide 作用下， 以 乙醚 为溶剂， 反应 3.0h， 生成 pent-2-yn-1-yl 4-methylbenzenesulfonate
  参考文献：
  名称：

  Total synthesis of (3Z,9Z,6S,7R) and (3Z,9Z,6R,7S)-6,7-epoxy-3,9-octadecadienes

  摘要：

  (3Z,9Z,6S,7R)-6,7-环氧-3,9-十八碳二烯(1)和(3Z,9Z,6R,7S)-6,7-环氧-3,9-十八碳二烯(2)已通过八步从2-戊炔-1-醇立体选择性地合成，总产率为8%。关键步骤涉及(2E)-2-辛-5-炔-1-醇(6)的Sharpless不对称双羟化。新的合成方法适用于1和2的克级制备，并可用于生产足够数量的性信息素组分，以管理茶园害虫。[图形]。

  DOI：

  10.1080/00397911.2017.1342842

文献信息

• A Modular, Enantioselective Synthesis of Resolvins D3, E1, and Hybrids
  作者：Felix Urbitsch、Bryony L. Elbert、Josep Llaveria、Penelope E. Streatfeild、Edward A. Anderson

  DOI：10.1021/acs.orglett.0c00089

  日期：2020.2.21

  Here, we report a convergent and flexible strategy to prepare these natural products using Hiyama-Denmark coupling of five- and six-membered cyclic alkenylsiloxanes to connect three resolvin fragments, and control the stereochemistry of the natural product (Z)-alkenes. The modular nature of this approach enables the synthesis of novel resolvin hybrids, opening up opportunities for more-extensive investigations

  Resolvins D3和E1是解决炎症的重要信号分子。在这里，我们报告了一种收敛和灵活的策略，使用五元和六元环状烯基硅氧烷的Hiyama-Denmark偶联制备这些天然产物，以连接三个resolvin片段，并控制天然产物（Z）-烯烃的立体化学。这种方法的模块化性质使得能够合成新颖的RESOLVIN杂种，为进行RESOLVIN生物学的更广泛的研究提供了机会。
• Process for preparing (4Z,7Z)-4,7-decadien-1-yl acetate
  申请人：SHIN-ETSU CHEMICAL CO., LTD.

  公开号：US10221123B1

  公开（公告）日：2019-03-05

  A high-yield process for preparing (4Z,7Z)-4,7-decadien-1-yl acetate, with reduced number of steps, without using a protecting group. A process for preparing (4Z,7Z)-4,7-decadien-1-yl acetate is provided, the process including at least the following steps: reducing a 10-halo-3,6-decadiyne of the general formula (1) to form a (3Z,6Z)-10-halo-3,6-decadiene of the general formula (2); and converting the (3Z,6Z)-10-halo-3,6-decadiene into (4Z,7Z)-4,7-decadien-1-yl acetate of the formula (4) having an acetoxy group in place of the halogen atom of the (3Z,6Z)-10-halo-3,6-decadiene.

  提供了一种制备(4Z,7Z)-4,7-癸二烯-1-醋酸酯的高产率工艺，步骤减少，无需使用保护基团。制备(4Z,7Z)-4,7-癸二烯-1-醋酸酯的工艺包括至少以下步骤：将通式(1)的10-卤代-3,6-癸二炔还原以形成通式(2)的(3Z,6Z)-10-卤代-3,6-癸二烯；将(3Z,6Z)-10-卤代-3,6-癸二烯转化为具有乙酰氧基取代(3Z,6Z)-10-卤代-3,6-癸二烯卤原子的通式(4)的(4Z,7Z)-4,7-癸二烯-1-醋酸酯。
• [EN] METHOD FOR THE SYNTHESIS OF DHA<br/>[FR] PROCÉDÉ DE SYNTHÈSE DE DHA
  申请人：PHENOMENOME DISCOVERIES INC

  公开号：WO2012126088A1

  公开（公告）日：2012-09-27

  A method for preparing docosahexaenoic acid (DHA). The method comprises coupling a compound represented by Formula I with a compound represented by Formula II followed by partial hydrogenation to obtain a compound represented by Formula III. The compound represented by Formula III acts as a DHA precursor and thus can be hydrolysed to obtain DHA. Novel starting materials represented by Formula I and Formula II, and synthetic routes for preparing the same are also provided.

  一种制备二十二碳六烯酸（DHA）的方法。该方法包括将由式I表示的化合物与由式II表示的化合物偶联，然后进行部分氢化以获得由式III表示的化合物。由式III表示的化合物作为DHA前体，因此可以水解得到DHA。还提供了由式I和式II表示的新型起始物质，以及用于制备它们的合成路线。
• Propargylether derivatives
  申请人：Syngenta Participations AG

  公开号：US06469005B1

  公开（公告）日：2002-10-22

  Propargylether derivatives of formula I including the optical isomers thereof and mixtures of such isomers, wherein R1 is hydrogen, alkyl, cycloalkyl or optionally substituted aryl, R2 and R3 are each independently hydrogen or alkyl, R4 is alkyl, alkenyl or alkynyl, R5, R6, R7, and R8 are each independently hydrogen or alkyl and R9 is a group R10 is optionally substituted aryl or optionally substituted heteroaryl, R11 is hydrogen or optionally substituted alkyl, alkenyl or alkynyl, Z is hydrogen —CO—R16, —COOR16, —CO—COOR16 or —CONR16R17, R12 is hydrogen, or optionally substituted alkyl, alkenyl or alkynyl, R13 is hydrogen or alkyl, R14 is hydrogen, alkyl, cycloalkyl or cycloalkyl-alkyl, R15 is alkyl, alkenyl, alkynyl, optionally substituted aryl or optionally substituted aryl-alkyl, and R16 and R17 are independently of each other hydrogen, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted aryl or optionally substituted heteroaryl, have been found to be useful for controlling or preventing the infestation of plants by phytopathogenic microorganisms, especially fungi. The invention relates the novel compounds and also to the preparation thereof and to the use of the compounds for plant protection, and to compositions suitable for applying the novel compounds in agricultural techniques.

  式I的Propargylether衍生物包括其光学异构体和这些异构体的混合物，其中R1是氢，烷基，环烷基或可选择取代的芳基，R2和R3分别独立地是氢或烷基，R4是烷基，烯基或炔基，R5、R6、R7和R8分别独立地是氢或烷基，R9是基团，R10是可选择取代的芳基或可选择取代的杂环芳基，R11是氢或可选择取代的烷基，烯基或炔基，Z是氢，-CO-R16，-COOR16，-CO-COOR16或-CONR16R17，R12是氢或可选择取代的烷基，烯基或炔基，R13是氢或烷基，R14是氢，烷基，环烷基或环烷基-烷基，R15是烷基，烯基，炔基，可选择取代的芳基或可选择取代的芳基-烷基，R16和R17独立地是氢，可选择取代的烷基，可选择取代的环烷基，可选择取代的芳基或可选择取代的杂环芳基，已被发现对控制或预防植物受植物病原微生物，尤其是真菌的侵害具有有用性。该发明涉及新颖的化合物，以及其制备和用于植物保护的化合物的用途，以及适用于在农业技术中应用新化合物的组合物。
• Synthesis of deuterium labeled polyunsaturated fatty acids
  作者：Aleš Svatoš、Athula B. Attygalle、Jerrold Meinwald

  DOI：10.1016/0040-4039(94)88495-1

  日期：1994.12

  Compounds containing carbon-carbon double bonds bearing cis deuterium atoms can be prepared conveniently by treating disubstituted acetylenes with bis(2-deuteriocyclohexyl)borane-B-D1 [DB(Cy)2] followed by reaction with CH3CO2D. As an example, the preparation of labeled linolenic acid is reported.

  通过用双（2-氘代环己基）硼烷-BD 1 [DB（Cy）2 ]处理二取代的乙炔，然后与CH 3 CO 2 D反应，可以方便地制备含有带有顺式氘原子的碳-碳双键的化合物。 ，报道了标记的亚麻酸的制备。