4-methyl-3-decen-1-yne | 188245-14-9

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: 4-methyl-3-decen-1-yne
• 英文别名: 4-methyl-dec-3-en-1-yne；(E)-4-methyldec-3-en-1-yne
• CAS: 188245-14-9
• 化学式: C₁₁H₁₈
• 分子量: 150.264
• InChiKey: VHEVGGXJBKULLD-PKNBQFBNSA-N

物化性质

• 沸点：
  192.8±9.0 °C(Predicted)
• 密度：
  0.802±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.64
• 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：

  4-methyl-3-decen-1-yne 在 AD-mix-α 、 正丁基锂 、 甲基磺酰胺 、 二氯乙基铝 、 三氟乙酸 作用下， 以 水 、 叔丁醇 为溶剂， 反应 4.5h， 生成
  参考文献：
  名称：

  A Highly Efficient Synthesis of (−)-PI-091 Construction of the 4-Alkoxy-2-butene-4-lactam Skeleton from Fischer-Type Carbene Complexes, Alkynyllithiums, and Tosyl Isocyanate

  摘要：

  DOI：

  10.1021/jo9700686
• 作为产物：
  描述：

  1-辛炔 在 哌啶 、 双(乙腈)氯化钯(II) 、 copper(l) iodide 、 二氯二茂锆 、 四丁基氟化铵 、 碘 作用下， 以 二氯甲烷 为溶剂， 生成 4-methyl-3-decen-1-yne
  参考文献：
  名称：

  A Highly Efficient Synthesis of (−)-PI-091 Construction of the 4-Alkoxy-2-butene-4-lactam Skeleton from Fischer-Type Carbene Complexes, Alkynyllithiums, and Tosyl Isocyanate

  摘要：

  DOI：

  10.1021/jo9700686

文献信息

• Catalytic Asymmetric Vinylation and Dienylation of Ketones
  作者：Hongmei Li、Patrick J. Walsh

  DOI：10.1021/ja0425740

  日期：2005.6.1

  tolerant of functional groups, including alkyl, aryl and vinyl halides, esters, silyl protected alcohols, sulfides, and alkenes. Thus, enantioenriched tertiary allylic alcohols bearing a variety of functional groups can be prepared. It has also been found that 2,2-disubstituted vinylzinc reagents, substitution patterns not accessible through hydrozirconation, can be added to ketones with high enantioselectivities

  报告了酮催化不对称乙烯基化的长期问题的解决方案。乙烯基锌试剂是通过末端炔烃的氢锆化，然后金属转移为锌而产生的。在我们的催化剂（由双（磺酰胺）二醇配体 (1) 和四异丙醇钛原位形成）存在下，乙烯基锌试剂与具有对映选择性（通常 >90%）的各种酮和烯酮发生 1,2-加成) 和高收益。该方法可耐受官能团，包括烷基、芳基和乙烯基卤化物、酯、甲硅烷基保护的醇、硫化物和烯烃。因此，可以制备带有多种官能团的对映体富集的叔烯丙醇。还发现 2,2-二取代的乙烯基锌试剂，无法通过氢化锆化作用获得的取代模式，可以添加到具有高对映选择性的酮中以生成三取代的烯丙醇。此外，我们已经开发出在我们的催化剂存在下二烯基与酮的不对称加成。该方法能够以高产率合成二烯醇，对映选择性高达 94%。
• Dimethylzinc-Mediated Additions of Alkenylzirconocenes to Aldimines. New Methodologies for Allylic Amine and <i>C</i>-Cyclopropylalkylamine Syntheses
  作者：Peter Wipf、Christopher Kendall、Corey R. J. Stephenson

  DOI：10.1021/ja028092a

  日期：2003.1.1

  Hydrozirconation of alkynes with zirconocene hydrochloride followed by in situ transmetalation to dimethylzinc provides access to reactive alkenyl organometallic reagents from readily available precursors. Upon addition of imines, 1,2-attack leads to synthetically useful allylic amine building blocks. In the presence of CH2I2 or CH2Cl2, the N-metalated allylic amide intermediate is cyclopropanated and C-cyclopropylalkylamines are formed in high yield and excellent diastereoselectivities favoring the anti products. The use of enynes as starting materials for this domino reaction provides conjugated biscyclopropanes and thus allows the stereoselective formation of five new carbon-carbon bonds. A transition state that explains the need for both zirconocene complex and alkyl zinc in the cyclopropanation reaction is proposed.
• Direct Synthesis of Terminal Alkynes <i>via</i> Pd-Catalyzed Cross Coupling of Aryl and Alkenyl Halides with Ethynylmetals Containing Zn, Mg, and Sn. Critical Comparison of Countercations
  作者：Ei-ichi Negishi、Martin Kotora、Caiding Xu

  DOI：10.1021/jo971552b

  日期：1997.12.1
• Sustainable HandaPhos-<i>ppm</i> Palladium Technology for Copper-Free Sonogashira Couplings in Water under Mild Conditions
  作者：Sachin Handa、Justin D. Smith、Yitao Zhang、Balaram S. Takale、Fabrice Gallou、Bruce H. Lipshutz

  DOI：10.1021/acs.orglett.7b03621

  日期：2018.2.2

  Complexation of ca. 1000 ppm Pd(OAc)(2) with the ligand HandaPhos (1-1.5:1) leads to a precatalyst that efficiently mediates Sonogashira couplings in aqueous nano micelles under very mild conditions. Neither copper nor organic solvent is required in the reaction medium, and the product can be isolated directly from the reaction flask, leaving behind a reaction mixture that can be recycled without additional additives.
• Dimethylzinc-Mediated Addition of Alkenylzirconocenes to α-Keto and α-Imino Esters
  作者：Peter Wipf、Corey R. J. Stephenson

  DOI：10.1021/ol0347141

  日期：2003.7.1

  graphicHydrozirconation of alkynes followed by in situ transmetalation to dimethylzinc and 1,2-addition to activated ketones and N-diphenylphosphinoylimines leads to tertiary allylic alcohols and amines in high overall yield. With 8-phenylmenthol as the chiral auxiliary, si-face attack proceeds in good to excellent diastereoselectivitles.