1-phenylundeca-1,2-diene | 27694-89-9

• 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: 1-phenylundeca-1,2-diene
• 英文别名: undeca-1,2-dienylbenzene；1-phenyl-1,2-undecadiene；1,2-Undecadienylbenzene
• CAS: 27694-89-9
• 化学式: C₁₇H₂₄
• 分子量: 228.378
• InChiKey: IINHOPJIHBUNMP-UHFFFAOYSA-N

物化性质

• 沸点：
  133-134 °C(Press: 0.5 Torr)
• 密度：
  0.8901 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 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：

  1-phenylundeca-1,2-diene 在 (PhO)3PAuCl 、 叠氮基三甲基硅烷 、 silver trifluoromethanesulfonate 、 三氟乙酸 作用下， 以 二氯甲烷 、 水 为溶剂， 以76%的产率得到
  参考文献：
  名称：

  一种新的金催化的异戊二烯叠氮化。

  摘要：

  作为一种新的高度模块化的方法，提出了一种新的金催化的丙二烯叠氮化反应，该方法可从简单的前体合成含氮的取代烯丙基衍生物。

  DOI：

  10.1039/c3cc48017h
• 作为产物：
  描述：

  1-(1-phenylundec-2-yn-1-yl)pyrrolidine 在 zinc(II) iodide 作用下， 以 甲苯 为溶剂， 反应 12.0h， 生成 1-phenylundeca-1,2-diene
  参考文献：
  名称：

  Mild-Condition Synthesis of Allenes from Alkynes and Aldehydes Mediated by Tetrahydroisoquinoline (THIQ)

  摘要：

  A practical 1,2,3,4-tetrahydroisoquinoline (THIQ)-mediated synthesis of 1,3-disubstituted allenes from terminal alkynes and aldehydes under mild conditions in the presence of CuBr first and then ZnI2 was reported. This telescoped allene synthesis reaction includes three consecutive steps and two reactions: first, a room-temperature CuBr-catalyzed synthesis of propargylamines, exo-yne-THIQs, from terminal alkynes, aldehydes, and THIQ then filtration of the CuBr catalyst, and finally the ZnI2-mediated allene synthesis from the generated exo-yne-THIQs under mild conditions (either at room temperature or heating at 50 or 75 degrees C). A wide range of aliphatic or aromatic aldehydes and terminal alkynes are tolerated, affording the allene products in up to 92% yield. Especially, temperature-sensitive aldehydes can be used in the reaction system. Preliminary exploration of the asymmetric allene synthesis has also been conducted, and a moderate enantioselectivity has been achieved. Finally, the relative reactivities of several secondary amines were compared with THIQ, showing that THIQ is the best of these amines in the synthesis of allenes under mild reaction conditions.

  DOI：

  10.1021/jo4018183

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)。
• Room Temperature Allenation of Terminal Alkynes with Aldehydes
  作者：Junzhe Xiao、Yifan Cui、Can Li、Haibo Xu、Yizhan Zhai、Xue Zhang、Shengming Ma

  DOI：10.1002/anie.202109879

  日期：2021.12

  Au(SIPr)NTf2 has been identified for the room temperature ATA reaction to afford diverse 1,3-disubstituted allenes with 1-methyl-1,2,3,4-tetrahydroisoquinoline as amine and aldehyde and TFE or HFIP as the mediator. A formal synthesis of (−)-centrolobine and synthetic transformations have been demonstrated.

  Au(SIPr)NTf 2已被确定用于室温 ATA 反应，以提供不同的 1,3-二取代丙二烯，1-甲基-1,2,3,4-四氢异喹啉作为胺和醛，TFE 或 HFIP 作为介体。已经证明了 (-)-centrolobine 和合成转化的正式合成。
• Copper(I) Halide Promoted Diastereoselective Synthesis of Chiral Propargylamines and Chiral Allenes using 2-Dialkylaminomethylpyrrolidine, Aldehydes, and 1-Alkynes
  作者：Ramani Gurubrahamam、Mariappan Periasamy

  DOI：10.1021/jo302534f

  日期：2013.2.15

  Copper bromide promoted reactions of aldehydes, 1-alkynes, and chiral 2-dialkylaminomethylpyrrolidine at 25 °C give the corresponding chiral propargylamine derivatives in up to 96% yield and 99:1 dr that are readily converted to the corresponding disubstitued chiral allenes in up to 81% yield and 99% ee upon reaction with CuI in dioxane at 100 °C.

  在25°C下，溴化铜促进醛，1-炔烃和手性2-二烷基氨基甲基吡咯烷的反应，可以以高达96％的收率和99：1 dr的速率得到相应的手性炔丙基胺衍生物，这些衍生物很容易转化为相应的被破坏的手性丙二烯在100°C下与CuI在二恶烷中反应后，产率为81％，ee为99％。
• Ferric chloride-catalyzed C–N bond cleavage for the cyclization of arylallenes leading to polysubstituted indenes
  作者：Cong-Rong Liu、Ting-Ting Wang、Qing-Biao Qi、Shi-Kai Tian

  DOI：10.1039/c2cc36048a

  日期：——

  A range of arylallenes undergo carbocation-initiated cyclization reaction with N-benzylic and N-allylic sulfonamides in the presence of 10 mol% ferric chloride to give structurally diverse polysubstituted indenes in good yields with extremely high regioselectivity.

  一系列芳基烯丙基化合物在10 mol%的氯化铁存在下，与N-苄基和N-烯丙基磺酰胺发生碳阳离子引发的环化反应，生成结构多样的多取代茚类化合物，产率良好且区域选择性极高。
• TfOH/Fe(OTf)₃ Cocatalyzed Reaction of Arylallenes with Alcohols for Structurally Diverse Indene Derivatives
  作者：Congrong Liu、Haiyun Zhang、Lianghui Ding、Juan Liu

  DOI：10.1002/cjoc.201800099

  日期：2018.8

  The indene moiety is an important unit because of its presence in many chemical catalysts, functional materials and biologically relevant molecules. Herein, we report a facile reaction of arylallenes with benzylic or allylic alcohols through TfOH/Fe(OTf)3 cocatalyzed cleavage of sp3 carbon‐oxygen. In the presence of 5 mol% TfOH and 5 mol% Fe(OTf)3, a range of arylallenes undergo carbocation initiated

  茚部分是重要的单元，因为它存在于许多化学催化剂，功能材料和生物学相关的分子中。在本文中，我们报道了通过TfOH / Fe（OTf）3共同催化的sp 3碳氧裂解，芳基烯与苄醇或烯丙基醇的反应很容易。在5mol％的TfOH和5mol％的Fe（OTf）3的存在下，一定范围的芳基亚芳基与烷基醇进行碳正离子引发的环化反应，从而以优异的产率获得结构多样的多取代的茚基。H 2 O是使这种转变具有高度原子经济性和环境友好性的唯一副产物。