(3-cyclo-1-hexenyl-2-propynyl)benzene | 852031-50-6

• 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-cyclo-1-hexenyl-2-propynyl)benzene
• 英文别名: 3-(Cyclohexen-1-yl)prop-2-ynylbenzene
• CAS: 852031-50-6
• 化学式: C₁₅H₁₆
• 分子量: 196.292
• InChiKey: MUIYGOLFEIZDMG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  (3-cyclo-1-hexenyl-2-propynyl)benzene 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 以65%的产率得到(1R*,2R*)-1-(3-phenylpropynyl)-7-oxabicyclo[4.1.0]heptane
  参考文献：
  名称：

  水性介质中炔丙基环氧乙烷和氮丙啶的铂催化环化反应合成呋喃和吡咯

  摘要：

  描述了炔丙基环氧乙烷和氮丙啶与铂催化剂在水性介质中的反应。可通过炔丙基环氧乙烷的铂催化反应方便地合成具有各种取代基的呋喃。在N-碘代琥珀酰亚胺存在下的反应提供了3-碘取代的呋喃，其被高效地进一步官能化为四取代的呋喃。炔丙基氮丙啶也与铂催化剂反应，以良好的产率产生相应的取代的吡咯。 炔-环氧-呋喃-铂-吡咯

  DOI：

  10.1055/s-0029-1216867
• 作为产物：
  描述：

  3-苯-1-丙炔 在 正丁基锂 、 四甲基乙二胺 、 三氯氧磷 作用下， 以 四氢呋喃 、 吡啶 、 正己烷 为溶剂， 生成 (3-cyclo-1-hexenyl-2-propynyl)benzene
  参考文献：
  名称：

  Palladium-Catalyzed Diastereoselective Coupling of Propargylic Oxiranes with Terminal Alkynes

  摘要：

  A diastereoselective coupling of propargylic oxiranes with terminal alkynes has been developed with use of a palladium catalyst. The stereochemistries of the resulting 4-alkynyl-substituted 2,3-allenols have been altered depending on the palladium catalyst. An optically active anti-substituted allene was synthesized from the reaction of an enantiomerically enriched propargylic oxirane without loss of chirality.

  DOI：

  10.1021/ol070224n

文献信息

• Palladium-Catalyzed Heck Alkynylation of Benzyl Chlorides
  作者：Stephen Buchwald、Catharine Larsen、Kevin Anderson、Rachel Tundel

  DOI：10.1055/s-2006-949625

  日期：2006.11

  An efficient and general protocol for the palladium-catalyzed Heck alkynylation of benzyl chlorides was developed. A catalyst system comprised of PdCl 2 (CH 3 CN) 2 and 2-dicyclohexyl-phosphino-2',4',6'-triisopropylbiphenyl (XPhos), with CS 2 CO 3 as the base, efficiently couples a wide range of functionalized terminal alkynes and substituted benzyl chlorides at 65 °C. We have also demonstrated that

  开发了一种用于钯催化的苄基氯的 Heck 炔基化的高效通用方案。由 PdCl 2 (CH 3 CN) 2 和 2-二环己基-膦基-2',4',6'-三异丙基联苯 (XPhos) 组成的催化剂体系，以 CS 2 CO 3 为基础，有效地偶联了广泛的官能化末端炔烃和取代的苄基氯在 65 °C 下。我们还证明，可以选择相应的芳基丙二烯产物，以在一锅法中使用过量的碱和更高的反应温度 (80 °C)。
• 10.1021/acs.orglett.4c02216
  作者：Meher, Naresh Kumar、Suryavansi, Maruti、Geetharani

  DOI：10.1021/acs.orglett.4c02216

  日期：——

  Highly regioselective hydroboration of unsymmetrical internal alkynes remains a significant challenge for synthesizing valuable alkenylboronate esters. Herein, we describe an easily synthesizable pincer NHC-based Co complex as a catalyst for the cis-α selective hydroboration of unactivated internal alkynes and the cis-β selective hydroboration of activated internal alkynes with pinacolborane. The reaction

  不对称内炔烃的高区域选择性硼氢化仍然是合成有价值的烯基硼酸酯的重大挑战。在此，我们描述了一种易于合成的钳形 NHC 基 Co 配合物，作为未活化内炔烃的顺α选择性硼氢化和活化的内炔烃与频立硼烷的顺β选择性硼氢化的催化剂。该反应表现出高化学选择性、区域选择性和立体选择性，并且在无碱反应条件下催化剂表现出高效率和极低负载量。反应范围由具有多种官能团的炔烃证明。机理研究表明，一种可行的钴硼基中间体可以解释不寻常的区域选择性。
• Palladium-catalyzed cross-coupling reaction of alkynylzincs with benzylic electrophiles
  作者：Mingxing Qian、Ei-ichi Negishi

  DOI：10.1016/j.tetlet.2005.02.137

  日期：2005.4

  The reaction of alkynylzinc bromides with benzyl bromides or chlorides in the presence of a catalytic amount of Pd(DPE-phos)Cl-2 in THF at 23 degrees C cleanly produces the corresponding benzylated alkynes in 73-97% yields. With 10(-3) mol% of Pd(DPE-phos)Cl-2, the maximum turnover number of 7.1 x 10(4) has been observed for the formation of PhC CCH2Ph. (c) 2005 Published by Elsevier Ltd.
• Syntheses of Substituted Furans and Pyrroles by Platinum-Catalyzed Cyclizations of Propargylic Oxiranes and Aziridines in Aqueous Media
  作者：Masahiro Yoshida、Mohammad Al-Amin、Kozo Shishido

  DOI：10.1055/s-0029-1216867

  日期：2009.7

  aziridines with a platinum catalyst in aqueous media are described. Furans having a variety of substituents were conveniently synthesized by the platinum-catalyzed reaction of propargylic oxiranes. The reaction in the presence of N-iodosuccinimide afforded the 3-iodo-substituted furan, which was further functionalized to tetrasubstituted furans with high efficiency. Propargylic aziridines were also reacted

  描述了炔丙基环氧乙烷和氮丙啶与铂催化剂在水性介质中的反应。可通过炔丙基环氧乙烷的铂催化反应方便地合成具有各种取代基的呋喃。在N-碘代琥珀酰亚胺存在下的反应提供了3-碘取代的呋喃，其被高效地进一步官能化为四取代的呋喃。炔丙基氮丙啶也与铂催化剂反应，以良好的产率产生相应的取代的吡咯。 炔-环氧-呋喃-铂-吡咯
• Palladium-Catalyzed Diastereoselective Coupling of Propargylic Oxiranes with Terminal Alkynes
  作者：Masahiro Yoshida、Maiko Hayashi、Kozo Shishido

  DOI：10.1021/ol070224n

  日期：2007.4.1

  A diastereoselective coupling of propargylic oxiranes with terminal alkynes has been developed with use of a palladium catalyst. The stereochemistries of the resulting 4-alkynyl-substituted 2,3-allenols have been altered depending on the palladium catalyst. An optically active anti-substituted allene was synthesized from the reaction of an enantiomerically enriched propargylic oxirane without loss of chirality.