3-ethyl-1-phenyl-1-pentyn-3-ol | 73830-10-1

• 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: 3-ethyl-1-phenyl-1-pentyn-3-ol
• 英文别名: 3-ethyl-1-phenylpent-1-yn-3-ol；1-Pentyn-3-ol, 3-ethyl-1-phenyl-
• CAS: 73830-10-1
• 化学式: C₁₃H₁₆O
• 分子量: 188.269
• InChiKey: VCRLWQCXPNWHJX-UHFFFAOYSA-N

物化性质

• 沸点：
  138-142 °C(Press: 12 Torr)
• 密度：
  1.01±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 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：

  3-ethyl-1-phenyl-1-pentyn-3-ol 在 正丁基锂 、 二氯二茂锆 、 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 (3-ethylpenta-1,2-dien-1-yl)benzene
  参考文献：
  名称：

  在环境条件下，金催化的未活化的烯类异构化成1，3-二烯。

  摘要：

  我们已经开发了一种金活化的未活化的烯与亚硝基苯作为添加剂的异构化成1,3-二烯的异构化方法。对于高度取代的烯基，该反应几乎仅在室温下进行。该反应的效用通过烯丙基和反应性烯烃的一锅[4 + 2]-环加成反应得以体现。

  DOI：

  10.1039/c2cc32131a
• 作为产物：
  描述：

  (E)-β-chlorostyrene 在 iron(II) chloride 频哪酮 、 potassium tert-butylate 作用下， 以 二甲基亚砜 为溶剂， 反应 0.5h， 生成 3-ethyl-1-phenyl-1-pentyn-3-ol
  参考文献：
  名称：

  Competition of Mechanisms in Nucleophilic Substitution of Vinyl Halides. An Unequivocal Example of the Vinylic SRN1 Route1

  摘要：

  In a search for an unambiguous example of the vinylic S(RN)1 route, several vinyl bromides and iodides were reacted mostly with (-)CH(2)COCMe(3), and sometimes with (-)CH(2)COPh, (CH)-C--(Me)COEt, and (EtO)(2)PO- ions, under Fe2+- or photostimulation in Me(2)SO. Vinyl halides having vinylic hydrogens, such as beta-bromostyrene, gave acetylenic products, e.g., phenylacetylene or a tertiary PhC=C-substituted alcohol, whereas vinyl halides with allylic hydrogens, such as Me(2)C=C(I)CHMe(2), gave a substituted allene. Reduction products of the halogen, as well as substitution and rearranged substitution products, were also formed. The operation of ionic elimination-addition routes accounts for formation of most of the products, while the reduction products arise from an intermediate vinyl radical. Ph(2)C=C(Br)Ph (20) and Me(2)C=C(Br)Ph (25) gave both substitution and reduction products, but Me(2)C=C(Br)-t-Bu (23) gave only a reduction product. Formation of substitution products from the conjugated 20 and 25 was ascribed to a reaction via a vinylic S(RN)1 route, while lack of substitution in 23 is related to its nonconjugated system and to the consequent higher energy that the radical anion of the substitution product would have. The one here reported seems to be the first case of an exclusive genuine vinylic S(RN)1 process.

  DOI：

  10.1021/jo00101a045

文献信息

• Palladium(II)/N-Heterocyclic Carbene-Catalyzed Regioselective Heteroannulation of Tertiary Propargyl Alcohols and<i>o</i>-Haloanilines to form 2-Alkenylindoles
  作者：Pradeep Kumar Reddy Panyam、Thirumanavelan Gandhi

  DOI：10.1002/adsc.201601349

  日期：2017.4.3

  Monometallic and bimetallic palladium(II)/N‐heterocyclic carbene complexes appended with naphthalimide or bisnaphthalimide moieties were designed, synthesized, and characterized. Employment of these catalysts brings about the step‐economic and regioselective heteroannulation of tertiary propargyl alcohols with o‐haloanilines resulting in biologically and pharmaceutically relevant 2‐alkenylindoles. Basis

  设计，合成和表征了单金属和双金属钯（II）/ N-杂环卡宾配合物，并附加了萘二甲酰亚胺或双萘二甲酰亚胺部分。这些催化剂的使用带来了叔炔丙醇与邻卤代苯胺的逐步经济和区域选择性杂成环化反应，从而产生了生物学上和药学上相关的2-烯基吲哚。通过在插入过程中炔丙基羟基部分与钯的配位，无法阐明区域选择性杂环化的基础。采用这种方法，可以通过后期修饰获得不对称的2,3-二取代吲哚的单一区域异构体。已经研究了将萘二甲酰亚胺或双萘二甲酰亚胺附加到NHC上对催化效率的作用。
• Microwave-Assisted Organocatalyzed Rearrangement of Propargyl Vinyl Ethers to Salicylaldehyde Derivatives: An Experimental and Theoretical Study
  作者：David Tejedor、Leandro Cotos、Daniel Márquez-Arce、Mikel Odriozola-Gimeno、Miquel Torrent-Sucarrat、Fernando P. Cossío、Fernando García-Tellado

  DOI：10.1002/chem.201503171

  日期：2015.12.7

  monocycles to complex fused polycyclic systems. The reaction is highly regioselective and takes place under symmetry‐breaking conditions. The preparative power of this reaction was demonstrated in the first total synthesis of morintrifolin B, a benzophenone metabolite isolated from the small tree Morinda citrifolia L. A DFT study of the reaction was performed with full agreement between calculated values and

  描述了微波辅助的咪唑催化的炔丙基乙烯基醚（PVE）到多取代的水杨醛的转化。该反应在仪器上简单，可扩展，并且在起始PVE的炔丙基位置容许不同程度的取代。生成的水杨醛基序包含多种拓扑结构，从简单的芳族单环到复杂的稠合多环系统。该反应是高度区域选择性的，并且在对称性破坏条件下发生。从小树巴戟天分离出的二苯甲酮代谢物morintrifolin B的第一个全合成中证明了该反应的制备能力。L.在计算值与实验结果完全一致的情况下进行了反应的DFT研究。从理论上计算出的值支持一种多米诺机制，该机制包括炔丙基克莱森重排，[1,3] -H位移，[1,7] -H位移（烯化），6π电环化和芳构化反应。
• Ru(<scp>ii</scp>)-catalyzed allenylation and sequential annulation of <i>N</i>-tosylbenzamides with propargyl alcohols
  作者：Shreemoyee Kumar、Akshay M. Nair、Chandra M. R. Volla

  DOI：10.1039/d1cc01768c

  日期：——

  We hereby report Ru(II)-catalyzed C(sp2)–H allenylation of N-tosylbenzamides to access multi-substituted allenylamides. Furthermore, the allenylamides were converted to the corresponding isoquinolone derivatives via base mediated annulation. The current protocol features low catalyst loading, mild reaction conditions, high functional group compatibility and desired scalability. The unique functionality

  我们在此报告了 Ru( II ) 催化的N-甲苯磺酰苯甲酰胺的C(sp 2 )–H 烯丙基化以获得多取代的烯丙基酰胺。此外，通过碱介导的环化将丙二烯基酰胺转化为相应的异喹诺酮衍生物。目前的协议具有催化剂负载低、反应条件温和、官能团兼容性高和所需的可扩展性等特点。所提供的丙二烯的独特功能允许进一步转换以扩展协议的实用性。
• Gold(I)-Catalyzed Cascade Cyclization Reaction:  Highly Regio- and Diastereoselective Intermolecular Addition of Water and Alcohols to Epoxy Alkynes
  作者：Lun-Zhi Dai、Ming-Juan Qi、Yong-Ling Shi、Xu-Guang Liu、Min Shi

  DOI：10.1021/ol0713640

  日期：2007.8.1

  have developed a novel access to ketal skeletons through a highly regio- and diastereoselective intermolecular addition of water and alcohols to alkynyl epoxides catalyzed by gold(I). This procedure involves a domino three-membered ring-opening, 6-exo-cycloisomerization, and subsequent intra- or intermolecular nucleophilic addition to a double-bond sequence.

  我们已经开发了一种通过对金（I）催化的炔基环氧化物进行高度区域和非对映选择性分子间加水和醇的方法，从而获得了缩酮骨架的新途径。该过程涉及多米诺骨牌三元开环，6-外-环异构化，以及随后的向双键序列的分子内或分子间亲核加成。
• Studies on highly regio- and stereoselective hydration of 1,2-allenylic sulfoxides
  作者：Zhao Fang、Chao Zhou、Chunling Fu、Shengming Ma

  DOI：10.1039/c0ob00007h

  日期：——

  A highly regio- and stereoselective hydration of 1,2-allenylic sulfoxides in which proton served as the electrophile was reported. Through the X-ray diffraction study, it was concluded that the reaction may proceed via a 5-membered cyclic intermediate following by attack of the −OH at the sulfur atom.

  据报道，其中质子用作亲电子试剂的1，2-烯丙基亚砜具有高度的区域和立体选择性水合。通过X射线衍射研究，得出的结论是，反应可以进行经由由所述的攻击五元环状中间体如下-在OH硫 原子。