4-(1-decyn-1-yl)benzonitrile

• 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: 4-(1-decyn-1-yl)benzonitrile
• 英文别名: 4-Dec-1-ynylbenzonitrile
• 化学式: C₁₇H₂₁N
• 分子量: 239.36
• InChiKey: NGRVHZOFPDRQCC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-(1-decyn-1-yl)benzonitrile 在 盐酸 、 6-chloro-3-((dimethylamino)(dimethyliminio)methyl)-1H-benzo[d][1,2,3]triazol-3-ium-1-olatehexafluorophosphate(V) 、 盐酸羟胺 、 三乙胺 、 N,N-二异丙基乙胺 、 对甲苯磺酰肼 作用下， 以 甲醇 、 乙二醇二甲醚 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 (S)-3-(4-decylphenyl)-5-(pyrrolidin-2-yl)-1,2,4-oxadiazole
  参考文献：
  名称：

  Structure–activity relationship studies of the lipophilic tail region of sphingosine kinase 2 inhibitors

  摘要：

  Sphingosine-1-phosphate (S1P) is a ubiquitous, endogenous small molecule that is synthesized by two isoforms of sphingosine kinase (SphK1 and 2). Intervention of the S1P signaling pathway has attracted significant attention because alteration of S1P levels is linked to several disease states including cancer, fibrosis, and sickle cell disease. While intense investigations have focused on developing SphK1 inhibitors, only a limited number of SphK2-selective agents have been reported. Herein, we report our investigations on the structure-activity relationship studies of the lipophilic tail region of SLR080811, a SphK2-selective inhibitor. Our studies demonstrate that the internal phenyl ring is a key structural feature that is essential in the SLR080811 scaffold. Further, we show the dependence of SphK2 activity and selectivity on alkyl tail length, suggesting a larger lipid binding pocket in SphK2 compared to SphK1. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.03.041
• 作为产物：
  描述：

  1-癸炔 在 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 正丁基锂 、 caesium carbonate 作用下， 以 四氢呋喃 、 正己烷 、 水 为溶剂， 反应 17.0h， 生成 4-(1-decyn-1-yl)benzonitrile
  参考文献：
  名称：

  suzuki-miyaura交叉偶联反应的发展：空气稳定的炔基三氟硼酸钾在芳基的炔基化反应中的应用。

  摘要：

  炔基三氟硼酸钾与芳基卤化物或三氟甲磺酸酯的钯催化交叉偶联反应易于进行，产率中等至优异。炔基三氟硼酸钾是空气和水分稳定的结晶固体，可以无限期储存，这在组合化学应用中将具有优势。炔基交叉偶联反应可以使用9 mol％的PdCl2（dppf）.CH2Cl2作为催化剂，在THF或THF-H2O中，在Cs2CO3作为无机碱的情况下进行。两个伙伴都可以容忍各种功能组。

  DOI：

  10.1021/jo0262356

文献信息

• The Sonogashira coupling reaction catalyzed by ultrafine nickel(0) powder
  作者：Lei Wang、Pinhua Li、Yicheng Zhang

  DOI：10.1039/b314246a

  日期：——

  The Sonogashira coupling reaction catalyzed by ultrafine nickel(0) powder has been developed; terminal alkynes couple with aryl, alkenyl iodide and aryl bromide in the presence of cuprous iodide, triphenylphosphine, potassium hydroxide and ultrafine particle nickel(0) to provide the corresponding cross-coupling products with high yields.

  已开发由超细镍(0)粉末催化的Sonogashira偶联反应；末端炔烃在氯化铜、三苯基膦、氢氧化钾和超细镍(0)的存在下与芳基、烯基碘化物和芳基溴化物偶联，提供相应的交叉偶联产物，产率很高。
• Sonogashira cross-coupling reactions of aryl chlorides with alkynes catalysed by a tetraphosphine–palladium catalyst
  作者：Marie Feuerstein、Henri Doucet、Maurice Santelli

  DOI：10.1016/j.tetlet.2004.09.092

  日期：2004.11

  A range of aryl chlorides undergoes cross-couplings with alkynes in good yields in the presence of [PdCl(C3H5)](2)/cis,cis, cis-1,2,3,4-tetrakis(diphenylphosphinomethyl)cyclopentane as catalyst. A variety of aryl chlorides such as chloroacetophenone, chlorobenzonitrile, chloronitrobenzene, chloroanisole or chlorotoluene have been used successfully. The reaction also tolerates several alkynes such as phenylacetylene, dec-l-yne, ethynylcyclohexene or alk-l-ynols. Furthermore, this catalyst can be used at low loading with some substrates. (C) 2004 Elsevier Ltd. All rights reserved.
• Development of the Suzuki−Miyaura Cross-Coupling Reaction:  Use of Air-Stable Potassium Alkynyltrifluoroborates in Aryl Alkynylations
  作者：Gary A. Molander、Bryson W. Katona、Fouzia Machrouhi

  DOI：10.1021/jo0262356

  日期：2002.11.1

  cross-coupling reaction of potassium alkynyltrifluoroborates with aryl halides or triflates proceeds readily with moderate to excellent yields. The potassium alkynyltrifluoroborates are air- and moisture-stable crystalline solids that can be stored indefinitely, which will provide an advantage in applications to combinatorial chemistry. The alkynyl cross-coupling reaction can be effected using 9 mol % of PdCl2(dppf)

  炔基三氟硼酸钾与芳基卤化物或三氟甲磺酸酯的钯催化交叉偶联反应易于进行，产率中等至优异。炔基三氟硼酸钾是空气和水分稳定的结晶固体，可以无限期储存，这在组合化学应用中将具有优势。炔基交叉偶联反应可以使用9 mol％的PdCl2（dppf）.CH2Cl2作为催化剂，在THF或THF-H2O中，在Cs2CO3作为无机碱的情况下进行。两个伙伴都可以容忍各种功能组。
• Structure–activity relationship studies of the lipophilic tail region of sphingosine kinase 2 inhibitors
  作者：Molly D. Congdon、Elizabeth S. Childress、Neeraj N. Patwardhan、James Gumkowski、Emily A. Morris、Yugesh Kharel、Kevin R. Lynch、Webster L. Santos

  DOI：10.1016/j.bmcl.2015.03.041

  日期：2015.11

  Sphingosine-1-phosphate (S1P) is a ubiquitous, endogenous small molecule that is synthesized by two isoforms of sphingosine kinase (SphK1 and 2). Intervention of the S1P signaling pathway has attracted significant attention because alteration of S1P levels is linked to several disease states including cancer, fibrosis, and sickle cell disease. While intense investigations have focused on developing SphK1 inhibitors, only a limited number of SphK2-selective agents have been reported. Herein, we report our investigations on the structure-activity relationship studies of the lipophilic tail region of SLR080811, a SphK2-selective inhibitor. Our studies demonstrate that the internal phenyl ring is a key structural feature that is essential in the SLR080811 scaffold. Further, we show the dependence of SphK2 activity and selectivity on alkyl tail length, suggesting a larger lipid binding pocket in SphK2 compared to SphK1. (C) 2015 Elsevier Ltd. All rights reserved.