4-cyclohex-1-enylbut-3-yn-2-ol | 57210-37-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-cyclohex-1-enylbut-3-yn-2-ol
• 英文别名: 4-(1-cyclohexen-1-yl)-3-butyn-2-ol；4-(1'-cyclohexenyl)-3-butyn-2-ol；4-(cyclohex-1-en-1-yl)but-3-yn-2-ol；4-Cyclohex-1-enyl-but-3-in-2-ol；(+/-)-3-Hydroxy-1-(cyclohexen-(1)-yl)-butin-(1)；4-(Cyclohexen-1-yl)but-3-yn-2-ol
• CAS: 57210-37-4
• 化学式: C₁₀H₁₄O
• 分子量: 150.221
• InChiKey: IQKXLGXQECIXGI-UHFFFAOYSA-N

物化性质

• 沸点：
  82 °C(Press: 0.2 Torr)
• 密度：
  0.9740 g/cm3(Temp: 25 °C)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 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：

  4-cyclohex-1-enylbut-3-yn-2-ol 在 chromium(VI) oxide 、 溶剂黄146 、 乙酸乙酯 、 铂 作用下， 生成 4-环己基丁烷-2-酮
  参考文献：
  名称：

  Heilbron et al., Journal of the Chemical Society, 1949, p. 742,743

  摘要：

  DOI：
• 作为产物：
  描述：

  3-(1'-cyclohexenyl)-1-methyl-2-propynyl acetate 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 以84%的产率得到4-cyclohex-1-enylbut-3-yn-2-ol
  参考文献：
  名称：

  Synthesis of Glucosides Related to Grape and Wine Aroma Precursors

  摘要：

  Syntheses of the following glucosides are reported: 3',5',5'-trimethyl-3'-cyclohexenyl beta-D-glucopyranoside, 3'-(1 ''-cyclohexenyl)-1'-methyl-2'-propynyl-beta-D-glucopyranoside, (3'R*,9'S*)-3'-hydroxy-5'-megastigmen-7'-yn-9'-yl beta-D-glucopyranoside, (E,3'R*)-7'-oxo-5',8'-megastigmadien-3'-yl beta-D-glucopyranoside, and 4'-oxo-5'-megastigmen-9'-yl beta-D-glucopyranoside.

  DOI：

  10.1021/jf00052a025

文献信息

• One-Pot Synthesis of Optically Active Allyl Esters via Lipase−Vanadium Combo Catalysis
  作者：Shuji Akai、Ryosuke Hanada、Noboru Fujiwara、Yasuyuki Kita、Masahiro Egi

  DOI：10.1021/ol102053a

  日期：2010.11.5

  with a lipase produced the regio- and enantioconvergent transformation of racemic allyl alcohols (1 or 2) into optically active allyl esters. In this system, the vanadium compounds catalyzed the continuous racemization of the alcohols along with the transposition of the hydroxyl group, while the lipase effected the chemo- and enantioselective esterification to achieve the dynamic kinetic resolution.

  钒-氧代化合物（3或4）与脂肪酶的组合产生了外消旋烯丙醇（1或2）向光学和活性烯丙基酯的区域和对映体转化。在该系统中，钒化合物催化醇的连续外消旋化以及羟基的转位，而脂肪酶则实现化学和对映选择性酯化反应，以实现动态动力学拆分。
• Synthesis of substituted quinolines by the electrophilic cyclization of n-(2-alkynyl)anilines
  作者：Xiaoxia Zhang、Tuanli Yao、Marino A. Campo、Richard C. Larock

  DOI：10.1016/j.tet.2009.12.012

  日期：2010.2

  A wide variety of substituted quinolines are readily synthesized under mild reaction conditions by the 6-endo-dig electrophilic cyclization of N-(2-alkynyl)anilines by ICl, I2, Br2, PhSeBr, and p-O2NC6H4SCl. The reaction affords 3-halogen-, selenium- and sulfur-containing quinolines in moderate to good yields in the presence of various functional groups. Analogous quinolines bearing a hydrogen in the

  通过 ICl、I 2、Br 2、PhSeBr 和p -O 2 NC 6 H对N -(2-炔基)苯胺进行6-内位亲电环化，可以在温和的反应条件下轻松合成各种取代的喹啉。4 SCl。该反应在各种官能团存在下以中等至良好的产率提供含3-卤素、硒和硫的喹啉。通过Hg(OTf) 2催化这些相同的炔基苯胺的闭环，已经合成了在3-位带有氢的类似喹啉。
• Polymethylhydrosiloxane (PMHS) as an Additive in Sonogashira Reactions
  作者：Robert E. Maleczka Jr.、William P. Gallagher

  DOI：10.1055/s-2003-37522

  日期：——

  Polymethylhydrosiloxane (PMHS) in combination with CsF facilitates the Sonogashira reaction of a variety of alkynes and electrophiles. These couplings appear to involve the in situ formation and reaction of an alkynylsiloxane. Such couplings can be run amine free at room temperature, reaction times are short, workup is easy, and product purification is straightforward. Thus, the advantages (and disadvantages) of running Sonogashira couplings with 1-silylalkynes are realized, without the need to preform the alkynyl silane.

  聚甲基氢硅氧烷（PMHS）与氟化铯（CsF）结合，促进了多种炔烃与电亲核试剂的索诺加希拉反应。这些偶联反应似乎涉及到原位形成和反应炔基硅氧烷。这些偶联反应可以在室温下无胺进行，反应时间短，后处理简单，产品纯化直观。因此，利用1-硅基炔烃进行索诺加希拉偶联反应的优点（和缺点）得以实现，而无需预先制备炔基硅烷。
• PMHS-Mediated Couplings of Alkynes or Benzothiazoles with Various Electrophiles:  Application to the Synthesis of (−)-Akolactone A
  作者：William P. Gallagher、Robert E. Maleczka

  DOI：10.1021/jo034463+

  日期：2003.8.1

  Polymethylhydrosiloxane (PMHS) in combination with CsF facilitates the cross-coupling of alkynes or benzothiazoles with an array of vinyl, styryl, and aryl halides or nonaflates as well as acid chlorides. Experimental and spectroscopic evidence indicates that these reactions involve the in situ generation of a siloxyl intermediate. These cross-couplings proceed relatively quickly at room temperature

  聚甲基氢硅氧烷（PMHS）与CsF的结合有助于炔烃或苯并噻唑与一系列乙烯基，苯乙烯基和芳基卤化物或壬二酸酯以及酰基氯的交叉偶联。实验和光谱证据表明，这些反应涉及甲硅烷氧基中间体的原位生成。这些交叉偶联在室温和无胺条件下进行得相对较快。为了证明该方法的适用性，进行了全细胞毒性丁醇内酯（-）-可可内酯A的合成。
• Lipase-catalyzed asymmetric synthesis of naphtho[2,3-c]furan-1(3H)-one derivatives by a one-pot dynamic kinetic resolution/intramolecular Diels–Alder reaction: Total synthesis of (−)-himbacine
  作者：Koji Sugiyama、Shinji Kawanishi、Yasuhiro Oki、Marin Kamiya、Ryosuke Hanada、Masahiro Egi、Shuji Akai

  DOI：10.1016/j.bmc.2017.08.019

  日期：2018.4

  (Z)-3-(phenylsulfonyl)acrylate underwent an intramolecular Diels–Alder reaction in a one-pot procedure to produce an optically active naphtho[2,3-c]furan-1(3H)-one derivative (98% ee). This method was successfully applied to the asymmetric total synthesis of (−)-himbacine.

  很少研究使用通过醇的酶动力学动力学拆分而安装的酰基部分的一锅顺序反应。在这项工作中，通过脂肪酶/氧钒组合催化的外消旋二烯醇[4-（cyclohex-1-en-1-yl）but-3-en-2-ol或1-（ （Z）-3-（苯磺酰基）丙烯酸酯与环己基1-en-1-基）丁-2-烯-1-醇]通过一锅法进行分子内Diels-Alder反应以产生光学活性萘并[2,3 - c ]呋喃-1（3 H）-一衍生物（98％ee）。该方法已成功应用于（-）-半胱氨酸的不对称全合成。