5-己烯-3-炔-1-醇 | 28916-38-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 5-己烯-3-炔-1-醇
• 英文名称: hex-5-en-3-yn-1-ol
• CAS: 28916-38-3
• 化学式: C₆H₈O
• 分子量: 96.1289
• InChiKey: WNMUESKTGKNUAM-UHFFFAOYSA-N

物化性质

• 沸点：
  57-60 °C(Press: 8 Torr)
• 密度：
  0.9324 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  7
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5-己烯-3-炔-1-醇 在 Lindlar's catalyst 咪唑 、 TEA 、 氢气 、 碘 、 sodium hexamethyldisilazane 、 焦磷酸硫胺素 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 27.17h， 生成 (3Z,6Z,9S,10R)-9,10-epoxy-1,3,6-henicosatriene
  参考文献：
  名称：

  Total synthesis of enantiomers of (3Z,6Z)-cis-9,10-epoxy 1,3,6-henicosatriene — the pheromonal component of Diacrisia obliqua

  摘要：

  Synthesis of enantiomers of (3Z,6Z)-cis-9,10-epoxy 1,3,6-henicosatriene, the pheromonal component of Diacrisia obliqua was achieved through alkylative epoxide rearrangement and stereoselective Wittig olefination reactions as the key steps. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00389-5
• 作为产物：
  描述：

  tetrahydropyranyloxy hex-5-yne-3-ene 在 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 18.0h， 以90%的产率得到5-己烯-3-炔-1-醇
  参考文献：
  名称：

  Total synthesis of enantiomers of (3Z,6Z)-cis-9,10-epoxy 1,3,6-henicosatriene — the pheromonal component of Diacrisia obliqua

  摘要：

  Synthesis of enantiomers of (3Z,6Z)-cis-9,10-epoxy 1,3,6-henicosatriene, the pheromonal component of Diacrisia obliqua was achieved through alkylative epoxide rearrangement and stereoselective Wittig olefination reactions as the key steps. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00389-5

文献信息

• Palladium-catalyzed intramolecular cyanosilylation of alkynes leading to stereoselective synthesis of α,β-unsaturated nitriles
  作者：Michinori Suginome、Hiroshi Kinugasa、Yoshihiko Ito

  DOI：10.1016/s0040-4039(00)78457-7

  日期：1994.11

  cyanosilylation was achieved by the reaction of chlorodiphenylsilyl ether of homopropargylic alcohols with trimethylsilylcyanide in the presence of palladium catalyst. The reaction proceeded regio- and stereoselectively to give (Z)-3-(1-cyanoalkylidene)-2-silatetrahydrofurans, whose silyl group was transformed into various organic groups.

  分子内的氰基硅烷化反应是通过在钯催化剂存在下，均炔丙基醇的氯二苯基甲硅烷基醚与三甲基甲硅烷基氰化物反应来实现的。反应进行区域和立体选择，得到（Z）-3-（1-氰基亚烷基）-2-硅四氢呋喃，其甲硅烷基被转化成各种有机基团。
• Palladium-Catalyzed Aminomethylation and Cyclization of Enynol to O-Heterocycle Confined 1,3-Dienes
  作者：Houjian Yu、Bangkui Yu、Haocheng Zhang、Hanmin Huang

  DOI：10.1021/acs.orglett.1c01019

  日期：2021.5.21

  electrophilicity of the allylpalladium intermediates enables the regioselectively intramolecular 1,2-addition of enynol in the presence of aminal. This aminomethylation and cyclization reaction via C–N bond activation and intramolecular nucleophilic addition provides a rare example for the synthesis of O-containing heterocycle-confined 1,3-dienes, which is of synthetic potential for further derivatization. The method

  烯丙基钯中间体的亲电性的合理调节可在存在缩醛胺的情况下使烯醇的区域选择性地分子内1,2-加成。通过C–N键激活和分子内亲核加成反应进行的氨甲基化和环化反应为合成含O的杂环限定的1,3-二烯提供了一个罕见的例子，它具有进一步衍生化的合成潜力。该方法具有广泛的底物通用性以及官能团相容性，并且有效地提供了具有5个，6个和8元的具有各种官能团的含O杂环的所需产物的广泛范围。
• Insect sex pheromones: Palladium-catalyzed synthesis of aliphatic 1,3-enynes by reaction of 1-alkynes with alkenyl halides under phase transfer conditions
  作者：Renzo Rossi、Adriano Carpita、Maria G. Quirici、Maria L. Gaudenzi

  DOI：10.1016/0040-4020(82)80204-4

  日期：1982.1

  prepared in good yields by coupling reaction of 1-alkynes or ω-functionalized 1-alkynes halides in the presence of a catalytic amount of (PPh3)4Pd and Cul. The reactions, which were carried out under phase transfer conditions employing benzyltriethylammonium chloride as phase transfer agent, benzene as organic solvent and diluted aq NaOH as base, occurred with 100% stereospecificity when 1-halo-1-alkenes

  在催化量的（PPh 3）4 Pd和Cul存在下，通过1-炔烃或ω-官能化1-炔烃卤化物的偶合反应，已经以高收率制备了通式1的官能化1，3-酶。当使用定义构型的1-卤-1-烯烃时，以苄基三乙基氯化铵为相转移剂，苯为有机溶剂，稀NaOH水溶液为碱的相转移条件下发生的反应具有100％的立体特异性。这种偶联反应已被用于以高总产率制备一些纯昆虫性信息素组分或其前体。
• Stereodivergent Synthesis of Tertiary Fluoride-Tethered Allenes via Copper and Palladium Dual Catalysis
  作者：Shao-Qian Yang、Yi-Fan Wang、Wei-Cheng Zhao、Guo-Qiang Lin、Zhi-Tao He

  DOI：10.1021/jacs.1c03157

  日期：2021.5.19

  protocol for the unprecedented stereodivergent synthesis of tertiary fluoride-tethered allenes bearing a stereogenic center and stereogenic axis via Cu/Pd synergistic catalysis. A broad scope of conjugated enynes are coupled with various α-fluoroesters in high yields with high diastereoselectivities and generally >99% ee. In addition, the four stereoisomers of the allene products ensure precise access

  在本文中，我们描述了一种通过 Cu/Pd 协同催化对带有立体中心和立体轴的叔氟化物束缚丙二烯进行前所未有的立体发散合成的协议。广泛的共轭烯炔与各种α-氟代酯以高产率和高非对映选择性偶联，通常>99% ee。此外，丙二烯产物的四种立体异构体确保通过新型立体发散轴到中心手性转移过程精确获取氟化氢呋喃的相应四种立体异构体。
• Selective Indium-Mediated 1,2,4-Pentatrien-3-ylation of Carbonyl Compounds for the Efficient Synthesis of Vinyl Allenols
  作者：Jisu Park、Sung Hong Kim、Phil Ho Lee

  DOI：10.1021/ol802073q

  日期：2008.11.6

  highly selective synthetic method of functionalized vinyl allenols was developed from the reactions of various carbonyl compounds with organoindium reagent in situ generated from indium and 1-bromopent-4-en-2-yne derivatives. Treatment of vinyl allenols with gold catalyst, dienophile, or indium trihalide produced the functionalized dihydrofuran, cyclohexene, or 2-halo-1,3-diene derivatives in good to

  通过各种羰基化合物与由铟和1-溴戊-4-en-2-炔衍生物生成的有机铟试剂的反应，开发了一种高度选择性的官能化乙烯基烯丙醇的合成方法。用金催化剂，亲二烯体或三卤化铟处理乙烯基烯丙醇可以很好的产率获得官能化的二氢呋喃，环己烯或2-卤代-1,3-二烯衍生物。