2-hexen-4-yn-1-ol | 53497-80-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2-hexen-4-yn-1-ol
• 英文别名: hex-2-en-4-yn-1-ol；6-Hydroxy-hexen-(4)-in-(2)；Hex-2-en-4-in-1-ol.
• CAS: 53497-80-6；2807-19-4
• 化学式: C₆H₈O
• 分子量: 96.1289
• InChiKey: FOQPBGTTZIKXSH-UHFFFAOYSA-N

物化性质

• 沸点：
  199.9±23.0 °C(Predicted)
• 密度：
  0.942±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 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：

  2-hexen-4-yn-1-ol 在 lithium aluminium tetrahydride 、 3-O-benzyl-1,2-O-cyclohexylidene-α-D-glucofuranose 作用下， 生成 hexa-3,4-diene-1-ol
  参考文献：
  名称：

  氢化铝锂-3- O-苄基-1,2 - O-环己叉基-α-D-葡萄糖糠醛配合物的不对称还原以及天然丙二烯的绝对构型的确定

  摘要：

  DOI：

  10.1039/c19660000585
• 作为产物：
  描述：

  己-2,4-二炔-1-醇 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 生成 2-hexen-4-yn-1-ol
  参考文献：
  名称：

  Structure of gas phase [C5H6]+˙ ions

  摘要：

  AbstractCharge‐stripping spectra have been used to differentiate ionized cyclopentadiene from its acyclic isomers. The minimum amounts of translational energy lost during the charge‐stripping processes and the relative charge‐stripping efficiencies, which are also structurally important parameters, have been measured for these ionic species. [C5H6]+˙ ions, formed by dissociative ionization of various precursors in the ion source are found, usually, to be a mixture of cyclic and acyclic ions. In contrast, [C5H6]+˙ ions, derived from the dissociation of metastable molecular ions from a series of organic compounds, have the cyclopentadienyl structure. This structure was confirmed by collision‐induced dissociation of ions formed in the first field‐free region of a triple sector mass spectrometer.

  DOI：

  10.1002/oms.1210200316

文献信息

• Asymmetric syntheses. Part VII. Asymmetric reduction of ketones and alk-2-en-4-yn-1-ols with a lithium bismenthyloxyaluminium hydride complex; determination of the absolute configurations of allenic alcohols
  作者：R. James D. Evans、Stephen R. Landor、John P. Regan

  DOI：10.1039/p19740000552

  日期：——

  the former from (–)-(S)-α-chloroethyl 1-methylprop-2-ynyl ether involving elimination of hydrogen chloride followed by a Claisen sigmatropic rearrangement, and reduction of the resulting aldehyde. Asymmetric reduction of 4-methyl- and 4,4-dimethyl-pentan-2-ones with lithium bismenthyloxyaluminium hydride gave partially resolved (+)-4-methyl- and 4,4-dimethyl-pentan-2-ols.

  （+）-己-和（+）-庚-3,4-二烯醇可通过用二薄荷基氧基铝氢化锂还原六-和庚-2-en-4-yn-1-醇而容易地获得。已显示两个二烯酚均具有（+）- S-构型；前者由（–）-（S）-α-氯乙基1-甲基丙-2-炔基醚合成，其中涉及消除氯化氢，然后进行克莱森（Claisen）σ重排，并还原生成的醛，从而证实了这一点。用二薄荷基氧基铝氢化锂不对称还原4-甲基-和4,4-二甲基-戊烷-2-酮，得到部分拆分的（+）-4-甲基-和4,4-二甲基-戊烷-2-醇。
• Insertion d'allenes
  作者：J.L. Roustan、J.Y. Merour、C. Charrier、J. Benaim、P. Cadiot

  DOI：10.1016/s0022-328x(00)91995-8

  日期：1979.3

  The cyclisation of ηp1-alkyl-γ-allenic ligands of iron complexes into η2-allylcyclopentenone ligands has been achieved. As reaction intermediate an η1-acyl- ηp2-allenic chelate is characterised, which gives the cyclic product. The ring closure is viewed as a cis migration. suggesting a concerted pathway in the reactions where an /ghp2-allenic ligand is converted into an ηp3-allyl ligand.

  η的环化P1铁络合物的烷基- γ-丙二烯配位体为η 2 -allylcyclopentenone配体已经实现。作为反应中间体的η 1 -acyl-η P2 -allenic螯合物的特征，这使环状产物。闭环被视为顺式迁移。这表明在一个/ GH反应协调一致通路P2 -allenic配体被转换成η P3 -烯丙基配体。
• Combined coinage metal catalysis in natural product synthesis: total synthesis of (+)-varitriol and seven analogs
  作者：Tao Sun、Carl Deutsch、Norbert Krause

  DOI：10.1039/c2ob25069a

  日期：——

  A modular total synthesis of the natural product (+)-varitriol (1) and seven analogs was achieved by using combined coinage metal catalysis. Starting from enynol 13, reagent-controlled introduction of stereogenic centers and efficient center-to-axis-to-center chirality transfer via α-hydroxyallene 5 afforded (+)-varitriol with 6.4% yield over 10 steps.

  天然产物的模块化全合成 （+）-曲三醇（1）和七个类似物是通过组合造币金属催化制备的。从enynol开始13，试剂控制的引入手性中心，高效的经由中心到轴到中心的手性转移α-hydroxyallene 5，得到（+）-曲三醇 10步产率为6.4％。
• Stereocomplementary Syntheses of 1,ω‐Distannylated<i>E</i>,<i>Z</i>‐Isomeric Conjugated Trienes, Tetraenes, and Pentaenes
  作者：Jochen Burghart、Achim Sorg、Reinhard Brückner

  DOI：10.1002/chem.201001629

  日期：2011.5.27

  Stereoselective syntheses of 1,6‐bis(tributylstannyl)hexa‐1,3,5‐trienes, 1,8‐bis(tributylstannyl)octa‐1,3,5,7‐tetraenes, and 1,10‐bis(tributylstannyl)deca‐1,3,5,7,9‐pentaenes with various methylation patterns were achieved based on stereocomplementary CC bond‐forming reactions. All‐E isomers resulted from Ramberg–Bäcklund rearrangements of distannylated diallyl‐, allylpentadienyl‐, or bis‐ (pentadienyl)sulfones

  1,6-双（三丁基锡烷基）六-1,3,5-三烯，1,8-双（三丁基锡烷基）辛基-1,3,5,7-四烯和1,10-双（三丁基锡烷基）的立体选择性合成基于立体互补的CC键形成反应，获得了具有各种甲基化模式的十，1,3,5,7,9-戊烯。All- E异构体是由异戊二烯丙基二烯丙基，烯丙基戊二烯基或双（戊二烯基）砜的Ramberg-Bäcklund重排产生的。由Z 3取代的Bu 3 Sn取代的烯类或二烯与Bu 3 Sn取代的烯丙基或戊二烯基苯并噻唑基砜的（Sylvestre-）Julia烯化反应生成了单Z构型的1，ω-双（三丁基锡烷基）-1,3,5-多烯。相关拉姆贝格-兰迪亚办法提供清一色Ë-1-溴-6-（三丁基锡烷基）六-1,3,5-三烯但不清一色ë -1-（tetramethyldioxaborolanyl）-6-（三丁基锡烷基）六-1,3,5-三烯。
• The asymmetric synthesis and absolute configuration of allenic alcohols
  作者：R. J. D. Evans、S. R. Landor、J. P. Regan

  DOI：10.1039/c19650000397

  日期：——