3-(2-(phenylethynyl)phenyl)prop-2-yn-1-ol | 727975-12-4

• 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-(2-(phenylethynyl)phenyl)prop-2-yn-1-ol
• 英文别名: 3-(2-Phenylethynyl-phenyl)-prop-2-yn-1-ol；3-[2-(2-phenylethynyl)phenyl]prop-2-yn-1-ol
• CAS: 727975-12-4
• 化学式: C₁₇H₁₂O
• 分子量: 232.282
• InChiKey: NTKGZWHBHPSDFW-UHFFFAOYSA-N

物化性质

• 沸点：
  418.0±30.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 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-(2-(phenylethynyl)phenyl)prop-2-yn-1-ol 在 四溴化碳 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 6.17h， 以83%的产率得到1-(3-bromo-prop-1-ynyl)-2-phenylethynyl-benzene
  参考文献：
  名称：

  新型烯二炔连接的吡咯并[2,1- c ] [1,4]苯并二氮杂杂化合物的合成及其抗肿瘤活性

  摘要：

  描述了一系列与烯二炔连接的新型吡咯并[2,1- c ] [1,4]苯并二氮杂（PBD）杂种。通过DC-81（的C-8联制得这些化合物1）具有烯二炔（10 - 16通过碳链连接体，得到PBD混合剂）17 - 23以良好的收率。人类癌细胞系上的大多数杂种表现出更高的细胞毒性，并且sub-G1群体的数量比1增加。在上一篇文章中，我们已经证明DC-81-吲哚偶联剂（3-6）是黑色素瘤细胞凋亡的有效诱导剂。在本文中，我们研究了DC-81-烯二炔类药物是否比在人的293T细胞上显示6。我们的数据显示，用DC-81-烯二炔处理293T细胞导致膜联蛋白V结合，caspase-3降解和p53阻滞的显着增加，以识别凋亡细胞，这一结果比6更高。这些结果表明，DC-81-烯二炔剂在293T细胞中诱导凋亡的作用比DC-81-吲哚更有效。

  DOI：

  10.1016/j.bmc.2008.12.036
• 作为产物：
  描述：

  1-溴-2-苯基乙炔-苯 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 正丁基锂 、 三乙胺 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 13.0h， 生成 3-(2-(phenylethynyl)phenyl)prop-2-yn-1-ol
  参考文献：
  名称：

  Synthesis of Indeno-Fused Derivatives of Quinolizinium Salts, Imidazo[1,2-a]pyridine, Pyrido[1,2-a]indole, and 4H-Quinolizin-4-one via Benzannulated Enyne−Allenes

  摘要：

  [GRAPHICS]The benzannulated enediynyl propargylic alcohol 8 was prepared from 1-bromo-2-iodobenzene by two consecutive Sonogashira cross-coupling reactions. The subsequent transformation to mesylate 9 followed by treatment with 4-substituted pyridines 10 then furnished the benzannulated enediynes 11. On exposure of 11 to triethylamine, the indeno-fused quinolizinium salts 15 were produced in quantitative yield. Presumably the reaction proceeded through a 1,3-prototropic rearrangement to form the benzannulated enyne-allenes 12, which then underwent either a concerted Diels-Alder reaction or a two-step process involving a Schmittel cyclization reaction to form biradical 13 followed by an intramolecular radical-radical coupling to afford 14. A subsequent prototropic rearrangement then produced 15. Similarly, 21a and 21b were produced from 19a and 19b, respectively. The use of the Sonogashira reaction for cross-coupling between 1-iodo-2-(phenylethynyl)benzene (7) and 1-(2-propynyl)-1H-imidazole (25) followed by treatment of the resulting adduct with potassium tertbutoxide gave the indeno-fused imidazo[1,2-a]pyridine 24 in 98% yield. Similarly, the indeno-fused pyrido[1,2-a]indole 32 and 4H-quinolizin-4-one 35 were obtained by starting from 7 for cross-coupling with 1-(2-propynyl)-1H-indole (30) and 1-(2-propynyl)-2(1H)-pyridinone (33), respectively, followed by treatment with potassium tent-butoxide.

  DOI：

  10.1021/jo0505730

文献信息

• Gold‐Catalyzed Aminoaromatizations of 1,2‐Bis(alkynyl)benzenes with Anthranils to Yield 1‐Amino‐2‐napthaldehyde Products
  作者：Yashwant Bhaskar Pandit、Rai‐Shung Liu

  DOI：10.1002/adsc.202000591

  日期：2020.8.4

  Gold‐catalyzed aminoaromatizations of 1,n‐diynes with anthranils afforded 1‐amino‐2‐napthaldehyde derivatives efficiently. In this reaction sequence, anthranils preferably attack at gold‐coordinated prop‐3‐yn‐1‐ols to generate α‐imino gold carbenes that enable subsequent cyclizations with the other alkynes. Chemical functionalizations of the resulting 1‐amino‐2‐napthaldehydes are presented to manifest

  1，n-二炔与蒽的金催化氨基芳构化可有效地提供1-氨基-2-萘甲醛衍生物。在该反应顺序中，蒽优选攻击金配位的prop-3-yn-1-ol，生成α-亚氨基金卡宾，随后与其他炔烃环化。本文介绍了所得的1-氨基-2-萘甲醛的化学官能团，以证明这些反应的合成效用。
• Enantioselective Rh(II)-Catalyzed Desymmetric Cycloisomerization of Diynes: Constructing Furan-Fused Dihydropiperidines with an Alkyne-Substituted Aza-Quaternary Stereocenter
  作者：Rui Wu、Jiajun Lu、Tongxiang Cao、Jun Ma、Kai Chen、Shifa Zhu

  DOI：10.1021/jacs.1c07556

  日期：2021.9.15

  Described herein is an enantioselective dirhodium(II)-catalyzed cycloisomerization of diynes achieved by the strategy of desymmetrization, which not only represents a new cycloisomerization reaction of diynes but also constitutes the first Rh(II)-catalyzed asymmetric intramolecular cycloisomerization of 1,6-diynes. This protocol provides a range of valuable furan-fused dihydropiperidine derivatives

  本文描述了一种通过去对称化策略实现的对映选择性二炔（II）催化的二炔环异构化，它不仅代表了一种新的二炔环异构化反应，而且构成了第一个 Rh（II）催化的 1,6- 不对称分子内环异构化。迪因斯。该协议提供了一系列有价值的呋喃稠合二氢哌啶衍生物，其具有对映异构体富集的炔基取代氮杂四元立体中心，具有高效、完全的原子经济性和出色的对映选择性（高达 98% ee）。此外，高度功能化的产品可以很容易地转化为各种合成有用的构建块，并与一系列药物分子结合。涉及协调 [3+2] 环加成 /[1, 通过 DFT 计算和机理研究阐明了 Rh(II) 类卡宾中间体的 2]-H 位移。更重要的是，获得了炔-二铑 (II) 的第一个单晶，表明 η涉及由二铑 (II) 对炔醛的2 -协调活化。发现了羧酸盐配体和炔醛之间的弱氢键，这可能使明确定义的桨状二铑 (II) 在催化这种转化方面与其他金属配合物不同。此外，对映选择性的起源由
• A Practical method for preparation of β-glycosides of N-acetylglucosamine
  作者：Curtis F Crasto、Graham B Jones

  DOI：10.1016/j.tetlet.2004.04.127

  日期：2004.6

  A mild and efficient method for preparation of GlcNAc derivatives by reaction of glycosyl acceptors with glycosyl oxazolines has been developed. The key feature is use of Yb(OTf)3 as promoter, requiring moderate reaction times and equivalence stoichiometry. We anticipate application in the preparation of a wide range of derivatives of this biologically important class of building blocks.

  已经开发了通过糖基受体与糖基恶唑啉反应制备GlcNAc衍生物的温和有效的方法。关键特征是使用Yb（OTf）3作为促进剂，需要适度的反应时间和等效化学计量。我们预计将在制备这种具有生物学重要意义的构建基块的各种衍生物中应用。
• Synthesis of [1,2,3]Triazolo[5,1-<b><i>a</i></b>]isoquinoline Derivatives via a Selective Cascade Cyclization Sequence of 1,2-bis(Phenylethynyl)benzene Derivatives
  作者：Shipeng Tao、Qinquan Hu、Huan Li、Shan Ma、Yunfeng Chen

  DOI：10.1080/00397911.2015.1020952

  日期：2015.6.3

  derivatives, using a selective cascade cyclization of unsymmetrical substituted 1,2-bis(phenylethynyl)benzene derivatives with NaN3, has been developed. The reaction gave different substituted [1,2,3]triazolo[5,1-a]isoquinolines in moderate to good yields. It was found that the substituents on the alkynes were important for the selectivities of the cascade cyclization sequences. GRAPHICAL ABSTRACT

  摘要 采用不对称取代的 1,2-双（苯乙炔基）苯衍生物与 NaN3 的选择性级联环化，一种直接、简洁的合成方法，用于生成 [1,2,3] 三唑并 [5,1-a] 异喹啉衍生物， 已经被开发出来。该反应以中等至良好的产率得到不同的取代的[1,2,3]三唑并[5,1-a]异喹啉。发现炔烃上的取代基对级联环化序列的选择性很重要。图形概要
• Gold(I)‐Catalyzed Cascade Cyclization Reactions of Allenynes for the Synthesis of Fused Cyclopropanes and Acenaphthenes
  作者：Takaya Ikeuchi、Shinsuke Inuki、Shinya Oishi、Hiroaki Ohno

  DOI：10.1002/anie.201903384

  日期：2019.6.3

  A gold‐catalyzed reaction of phenylene‐tethered allenynes with benzofurans gave 1‐(naphth‐1‐yl)cyclopropa[b]benzofuran derivatives, whereas the reaction of 1‐allenyl‐2‐ethynyl‐3‐methylbenzene derivatives in the absence of benzofurans gave acenaphthenes in good yields. These results can be rationalized by nucleophilic attack of the alkyne moiety on an activated allene to form a vinyl cation intermediate

  亚苯基拴链的烯炔与苯并呋喃的金催化反应产生了1-（萘-1-基）环丙烷[ b ]苯并呋喃衍生物，而苯并呋喃不存在时1-烯基-2-乙炔基-3-甲基苯衍生物的反应以高收率得到啶。这些结果可以通过炔基部分在活化的丙二烯上的亲核攻击以形成乙烯基阳离子中间体来合理化。