1-<(2-Tetrahydropyranyl)oxy>tetradec-3-yne | 88730-56-7

• 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: 1-<(2-Tetrahydropyranyl)oxy>tetradec-3-yne
• 英文别名: 2-(tetradec-3-yn-1-yloxy)tetrahydro-2H-pyran；2-[(Tetradec-3-yn-1-yl)oxy]oxane；2-tetradec-3-ynoxyoxane
• CAS: 88730-56-7
• 化学式: C₁₉H₃₄O₂
• 分子量: 294.478
• InChiKey: YSKSITWWXKYFHK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  21
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 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：

  1-<(2-Tetrahydropyranyl)oxy>tetradec-3-yne 在 氢气 、 4-甲基苯磺酸吡啶 作用下， 以 乙醇 为溶剂， 生成 (Z)-十四碳-3-烯醇
  参考文献：
  名称：

  Synthesis of long-chain fatty acid derivatives as a novel anti-Alzheimer’s agent

  摘要：

  In order to develop new drugs for Alzheimer's disease, we prepared 17 fatty acid derivatives with different chain lengths and different numbers and positions of double bonds by using Wittig reaction and stereospecific hydrogenation of triple bonds as key reactions. Among them, (4Z,15Z)-octadecadienoic acid (10) and (23Z,34Z)-heptatriacontadienoic acid (16) showed the most potent neurite outgrowth activities on A beta(25-35)-treated rat cortical neurons, which activities were comparable to that of a positive control, NGF. Both fatty acids 10 and 16 possess two (Z)-double bonds at the n-3 and n-14 positions, which might be important for the neurite outgrowth activity. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.12.008
• 作为产物：
  描述：

  3,4-二氢-2H-吡喃 在 六甲基磷酰三胺 、 正丁基锂 、 4-甲基苯磺酸吡啶 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 1-<(2-Tetrahydropyranyl)oxy>tetradec-3-yne
  参考文献：
  名称：

  Synthesis of long-chain fatty acid derivatives as a novel anti-Alzheimer’s agent

  摘要：

  In order to develop new drugs for Alzheimer's disease, we prepared 17 fatty acid derivatives with different chain lengths and different numbers and positions of double bonds by using Wittig reaction and stereospecific hydrogenation of triple bonds as key reactions. Among them, (4Z,15Z)-octadecadienoic acid (10) and (23Z,34Z)-heptatriacontadienoic acid (16) showed the most potent neurite outgrowth activities on A beta(25-35)-treated rat cortical neurons, which activities were comparable to that of a positive control, NGF. Both fatty acids 10 and 16 possess two (Z)-double bonds at the n-3 and n-14 positions, which might be important for the neurite outgrowth activity. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.12.008

文献信息

• Alkylation of stabilized acetylides in DMSO. Preparation of α,β-acetylenic alcohols and acetals.
  作者：J.Michael Chong、Susanna Wong

  DOI：10.1016/s0040-4039(00)85233-8

  日期：1986.1

  Stabilized terminal acetylenes 1 [e.g. R=CH2OTHP, Ph, CH(OEt)2] may be converted into lithioacetylides and readily alkylated with 1° alkyl halides in DMSO to afford functionalized disubstituted acetylenes.

  稳定的末端乙炔1 [例如R = CH 2 OTHP，Ph，CH（OEt）2 ]可以转化为硫代乙炔，并易于在DMSO中用1°烷基卤化物进行烷基化，从而得到官能化的二取代乙炔。
• 매미나방의 성페로몬인 시스-7,8-에폭시-2-메틸옥타데칸의 합성방법
  申请人：주식회사 그린아그로텍 농업회사법인

  公开号：KR20240033428A

  公开（公告）日：2024-03-12

  본 발명은 매미나방의 성페로몬인 시스-7,8-에폭시-2-메틸옥타데칸의 합성방법에 관한 것으로, 특히 3-부틴올을 출발물질로 사용하고 Ni(OAc) 2 를 촉매로 사용한 촉매환원 반응과 그리냐르 반응으로 매미나방 페로몬인 시스-7,8-에폭시-2-메틸옥타데칸을 대량으로 합성하는 방법에 관한 것이다. 본 발명의 합성방법은, (a) 3-부틴올로부터 테트라덱-3-인-1-올을 합성하는 단계; (b) Ni(oAc) 2 촉매 하에 부분 수소화 반응시켜 시스-테트라덱-3-엔-1-올을 합성하는 단계; (c) 이소펜틸마그네슘 브로마이드로 그리냐르 반응시켜 시스-2-메틸옥타덱-7-엔을 합성하는 단계; 및 (d) 에폭시화 반응시켜 시스-7,8-에폭시-2-메틸옥타데칸을 합성하는 단계를 포함한다. 본 발명은, 출발물질로 3-부틴올을 사용하고 고가의 Pd 대신 저가의 Ni(OAc) 2 를 촉매로 사용한 촉매환원 반응과 그리냐르 반응으로, 매미나방 성페로몬인 시스-7,8-에폭시-2-메틸옥타데칸을 대량 합성할 수 있다. 본 발명에 따라 합성된 7,8-에폭시-2-메틸옥타데칸은 매미나방 성페로몬을 이용한 트랩에 유인제로 사용하여 야외에서 매미나방의 발생여부를 보다 쉽게 예찰할 수 있고, 이를 바탕으로 농가 등에 대량으로 포획트랩을 보급함으로써 화학농약을 사용하지 않는 환경친화적인 방법으로 해충인 매미나방을 방제할 수 있다.

  本发明涉及一种合成缢蛏_WEB construção蛾性信息素顺式-7,8-环氧-2-甲基-1-辛烯的方法，特别是一种以3-丁醇为起始原料，在Ni(OAc)₂催化下通过催化还原反应和格氏反应大量合成缢蛏_WEB construção蛾性信息素顺式-7,8-环氧-2-甲基-1-辛烯的方法。 本发明的合成方法包括以下步骤： (a) 以3-丁醇为原料合成四氢-3-甲基-1-丁醇的步骤； (b) 在Ni(OAc)₂催化下进行部分加氢反应，合成顺式-四氢-3-甲基-1-丁醇的步骤； (c) 以异戊基镁溴为格氏试剂进行格氏反应，合成顺式-2-甲基-7-辛烯的步骤； (d) 进行环氧化反应，合成顺式-7,8-环氧-2-甲基-1-辛烯的步骤。 本发明以3-丁醇为起始原料，使用廉价的Ni(OAc)₂代替昂贵的钯作为催化剂，通过催化还原反应和格氏反应，能够大量合成缢蛏_WEB construção蛾性信息素顺式-7,8-环氧-2-甲基-1-辛烯。根据本发明合成的7,8-环氧-2-甲基-1-辛烯可以用作诱芯，通过利用缢蛏_WEB construção蛾性信息素的诱捕器在户外更容易监测缢蛏_WEB construção蛾的发生情况，并在此基础上向农户等大量提供捕获诱捕器，从而通过不使用化学农药的环保方法防治害虫缢蛏_WEB construção蛾。
• Alkylation of 1-alkynes in THF
  作者：Matthew Buck、J.Michael Chong

  DOI：10.1016/s0040-4039(01)01131-5

  日期：2001.8

  Alkynes may be easily alkylated by sequential treatment with n-BuLi followed by an alkyl halide in THF. Primary iodides give excellent yields (75-99%) as do bromides in the presence of catalytic amounts of Bu4NI or NaI; in the absence of an iodide source, bromides react poorly. This method offers advantages over existing methods which use HMPA or NH3 as co-solvents. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Synthesis of .omega.-tritiated and .omega.-fluorinated analogs of the trail pheromone of subterranean termites
  作者：Joan F. Carvalho、Glenn D. Prestwich

  DOI：10.1021/jo00181a023

  日期：1984.4
• Synthesis of long-chain fatty acid derivatives as a novel anti-Alzheimer’s agent
  作者：Hong-Yan Zhang、Yu-ichiro Yamakawa、Yuji Matsuya、Naoki Toyooka、Chihiro Tohda、Suresh Awale、Feng Li、Shigetoshi Kadota、Yasuhiro Tezuka

  DOI：10.1016/j.bmcl.2013.12.008

  日期：2014.1

  In order to develop new drugs for Alzheimer's disease, we prepared 17 fatty acid derivatives with different chain lengths and different numbers and positions of double bonds by using Wittig reaction and stereospecific hydrogenation of triple bonds as key reactions. Among them, (4Z,15Z)-octadecadienoic acid (10) and (23Z,34Z)-heptatriacontadienoic acid (16) showed the most potent neurite outgrowth activities on A beta(25-35)-treated rat cortical neurons, which activities were comparable to that of a positive control, NGF. Both fatty acids 10 and 16 possess two (Z)-double bonds at the n-3 and n-14 positions, which might be important for the neurite outgrowth activity. (C) 2013 Elsevier Ltd. All rights reserved.