1-(3-methylhex-5-en-1-ynyl)benzene

• 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-(3-methylhex-5-en-1-ynyl)benzene
• 英文别名: (3-methyl-5-hexen-1-ynyl)benzene；(3-methylhex-5-en-1-ynyl)benzene；3-Methylhex-5-en-1-ynylbenzene
• 化学式: C₁₃H₁₄
• 分子量: 170.254
• InChiKey: ILKMDQRXBZEPIO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  4-苯基-3-丁炔-2-醇 在 三(五氟苯基)硼烷 4-二甲氨基吡啶 、 三乙胺 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 生成 1-(3-methylhex-5-en-1-ynyl)benzene
  参考文献：
  名称：

  Schwier, Todd; Rubin, Michael; Gevorgyan, Vladimir, Organic letters, 2004, vol. 6, # 12, p. 1999 - 2001

  摘要：

  DOI：

文献信息

• Indium(<scp>i</scp>)-catalyzed alkyl–allyl coupling between ethers and an allylborane
  作者：Hai Thanh Dao、Uwe Schneider、Shū Kobayashi

  DOI：10.1039/c0cc03673k

  日期：——

  An efficient method for alkyl–allyl cross-coupling between ethers and a 9-BBN-derived allylborane catalyzed by indium(I) triflate has been developed. The allylborane proved to be essential to obtain the desired products in high yields. The reaction displayed good substrate scope including high functional group tolerance.

  开发了一种高效的方法，用于通过三氟甲磺酸铟（I）催化的乙醚与9-BBN衍生烯丙基硼烷之间的烷基-烯丙基交联偶联反应。实验证明，烯丙基硼烷对于以高产率获得所需产物至关重要。该反应表现出良好的底物范围，包括对多种官能团的高容忍度。
• Rhenium-Catalyzed Coupling of Propargyl Alcohols and Allyl Silanes
  作者：Michael R. Luzung、F. Dean Toste

  DOI：10.1021/ja039124c

  日期：2003.12.1

  the high oxidation state rhenium complex allows for simple reisolation and reuse of the catalyst. A broad range of functional groups is tolerated including aryl halides, olefins, esters, and acid-labile functional groups such as acetals. Furthermore, displacement of the alcohol occurs preferentially even in the presence of other electrophiles such as primary alkyl halides and conjugated esters. The use

  描述了炔丙醇和烯丙基硅烷的区域选择性偶联的温和方法。该方法采用耐空气和耐湿的铼-氧配合物 ((dppm)ReOCl3) 作为形成 sp3-碳-sp3-碳键的催化剂，而无需事先将炔丙醇活化为卤化物或拟卤化物. 高氧化态铼配合物的稳定性允许催化剂的简单再分离和再利用。允许使用广泛的官能团，包括芳基卤化物、烯烃、酯和酸不稳定官能团，例如缩醛。此外，即使在其他亲电子试剂如伯烷基卤化物和共轭酯存在的情况下，也优先发生醇的置换。使用对映体纯巴豆基硅烷作为偶联伙伴允许两个相邻立体中心的不对称结构。该反应的潜力在 δ-内酯、二-O-甲基calopin 的不对称合成中得到证明。
• Multimetallic Ir–Sn3-catalyzed substitution reaction of π-activated alcohols with carbon and heteroatom nucleophiles
  作者：Arnab Kumar Maity、Paresh Nath Chatterjee、Sujit Roy

  DOI：10.1016/j.tet.2012.10.086

  日期：2013.1

  An atom economic and catalytic substitution reaction of π-activated alcohols by a multimetallic Ir–Sn3 complex has been demonstrated. The multimetallic Ir–Sn3 complex can be easily synthesized from the reaction between [Cp∗IrCl2]2 and SnCl2. In presence of as little as 1 mol % of the catalyst three different types of π-activated alcohols, namely benzyl, allyl, and propargyl alcohols, have been successfully

  已经证明了多金属Ir–Sn 3络合物的π活化醇的原子经济和催化取代反应。从[Cp ∗ IrCl 2 ] 2和SnCl 2之间的反应可以轻松合成多金属Ir-Sn 3络合物。在低至1 mol％的催化剂存在下，已使用碳将三种不同类型的π-活化醇，即苄基，烯丙基和炔丙基醇成功地转化为烷基化产物（芳烃，杂芳烃，烯丙基三甲基硅烷和1,3 （二羰基），氮（磺酰胺），氧（醇）和硫（硫醇）亲核试剂的收率非常高。Hammett相关性研究提出了一种亲电机理。
• A General and Efficient FeCl₃-Catalyzed Nucleophilic Substitution of Propargylic Alcohols
  作者：Zhuang-ping Zhan、Jing-liang Yu、Hui-juan Liu、Yuan-yuan Cui、Rui-feng Yang、Wen-zhen Yang、Jun-ping Li

  DOI：10.1021/jo061234p

  日期：2006.10.1

  A general and efficient FeCl3-catalyzed substitution reaction of propargylic alcohols with carbon- and heteroatom-centered nucleophiles such as allyl trimethylsilane, alcohols, aromatic compounds, thiols, and amides, leading to the construction of C−C, C−O, C−S and C−N bonds, has been developed.

  炔丙醇与碳和杂原子中心的亲核试剂（如烯丙基三甲基硅烷，醇，芳香族化合物，硫醇和酰胺）的一般有效的FeCl 3催化取代反应，导致C，C，O，C的构建已经开发了-S和C-N键。
• Nucleophilic Substitution of Secondary Alkyl-Substituted Propargyl Acetates: An Economic and Practical Indium Trichloride Catalyzed Access
  作者：Zhuang-ping Zhan、Min Lin、Lu Hao、Xiao-tao Liu、Qing-zhen Chen、Feng Wu、Ping Yan、Su-xia Xu、Xin-liang Chen、Jia-jie Wen

  DOI：10.1055/s-0030-1259557

  日期：2011.3

  An economic and practical transformation from secondary alkyl-substituted propargyl acetates to a variety of nucleophilic substitution products was described. This reaction was catalyzed by inexpensive InCl3. High yields and excellent chemoselectivity were obtained. The five-, six-, and seven-membered propargyl cyclo­ethers were also successfully constructed by this protocol.

  描述了一种经济实用的转化，将二级烷基取代的丙炔醇乙酸酯转化为多种亲核取代产物。该反应由廉价的氯化铟(InCl3)催化，获得了高产率和卓越的化学选择性。五元、六元和七元的丙炔环醚也通过该方法成功合成。