2-methyl-hept-1-en-6-yne | 67444-99-9

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: 2-methyl-hept-1-en-6-yne
• 英文别名: 6-Methyl-6-hepten-1-yn；2-Methylhept-1-en-6-yne
• CAS: 67444-99-9
• 化学式: C₈H₁₂
• 分子量: 108.183
• InChiKey: ZEOHPLPFOCOAMD-UHFFFAOYSA-N

物化性质

• 沸点：
  120.5±19.0 °C(Predicted)
• 密度：
  0.776±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  2-methyl-hept-1-en-6-yne 在 barium dihydroxide 、 lithium aluminium tetrahydride 作用下， 以 乙醇 为溶剂， 反应 8.0h， 生成
  参考文献：
  名称：

  Acetylenic bond participation in biomimetic polyene cyclizations. Preliminary model studies

  摘要：

  DOI：

  10.1021/ja00481a043
• 作为产物：
  描述：

  4-methyl-4-pentenyl-1-tosylate 、 乙炔氢锂 生成 2-methyl-hept-1-en-6-yne
  参考文献：
  名称：

  Acetylenic bond participation in biomimetic polyene cyclizations. Preliminary model studies

  摘要：

  DOI：

  10.1021/ja00481a043

文献信息

• Synthesis of Bicyclic Pyrane Derivatives via Tungsten-Mediated [3 + 3] Cycloaddition of Epoxides with Tethered Alkynes
  作者：Kuo-Hui Shen、Shie-Fu Lush、Tseng-Li Chen、Rai-Shung Liu

  DOI：10.1021/jo010698e

  日期：2001.11.1

  Propargyltungsten compounds bearing a tethered epoxide were prepared in short steps from readily available materials. In the presence of various Lewis acids, BF(3).Et(2)O catalysts (25 mol %) most effectively promote the [3 + 3] cycloaddition of the epoxide with its tethered propargyltungsten group, delivering bicyclic pyranyltungsten compounds in reasonable yields. This cyclization proceeds highly

  用容易获得的材料在短时间内制备了带有束缚的环氧化物的炔丙钨化合物。在各种路易斯酸的存在下，BF（3）.Et（2）O催化剂（25摩尔％）最有效地促进环氧基[3 + 3]与其束缚的炔丙基钨基团的环加成，以合理的产率提供双环吡喃钨化合物。该环化具有非对映选择性，并且对各种官能团具有耐受性。立体化学结果表明，环加成反应是通过炔丙基钨基团的外向攻击由环氧化物的开环引发的。使用不同的氧化剂将所得吡喃钨钨有机金属脱金属以产生各种双环吡喃基衍生物。如果在环化反应中使用手性环氧化物，则这种新方法可以快速合成双环含氧化合物的对映体。提出了一种机械模型来合理化这种[3 + 3]环加成反应的路径。
• Stereospecific Synthesis of Suspensolide, a Male-Produced Pheromone of the Caribbean Fruit Fly, Anastrepha suspensa (Loew), and the Mexican Fruit Fly, Anastrepha ludens (Loew)
  作者：Ginna Hidalgo-Del Vecchio、Allan C. Oehlschlager

  DOI：10.1021/jo00096a029

  日期：1994.8

  An efficient synthesis of (E,E)-4,8-dimethyl-3,8-decadien-10-olide, suspensolide, a major component of the pheromone blend of the Caribbean and Mexican fruit flies, is described. The synthesis involves dicarboalumination of 1,6-heptadiyne with in situ conversion to a dialanate and reaction with paraformaldehyde. Monoprotection of the symmetrical diol formed in this process as the mono-THP derivative allowed conversion of the free hydroxyl to the chloride (NCS/DMS). Addition of one carbon to the chain was achieved by displacement of the chloride by cyanide (phase-transfer conditions) or the lithium salt of a thioorthoester. Hydrolysis of the masked carbonyls and deprotection of the omega-hydroxyl gave (E,E)-4,8-dimethyl-10-hydroxy-3,8-decadienoic acid. This diunsaturated hydroxy acid was cyclized to suspensolide in 30% yield using Mitsunobu conditions. The overall yield of suspensolide in this eight-step synthesis was 10%.
• Thiophenol promoted cyclization of enynes
  作者：Chris A. Broka、David E.C. Reichert

  DOI：10.1016/s0040-4039(01)81027-3

  日期：1987.1
• Stereoselection in the chromium mediated intramolecular [2 + 2] cycloadditions of vinyl ketenes and alkenes
  作者：Oak K. Kim、William D. Wulff、Weiqin Jiang、Richard G. Ball

  DOI：10.1021/jo00073a001

  日期：1993.10

  The first study of the relative diastereoselectivity of the intramolecular [2 + 2] cycloadditions of alkenes and vinyl ketenes generated from the reactions of carbene complexes with chiral enynes is reported.
• BROKA CH. A.; REICHERT D. E. C., TETRAHEDRON LETT., 28,(1987) N 14, 1503-1506
  作者：BROKA CH. A.、 REICHERT D. E. C.

  DOI：——

  日期：——