(Z)-methyl non-2-enoate | 1402932-15-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (Z)-methyl non-2-enoate
• CAS: 1402932-15-3
• 化学式: C₁₀H₁₈O₂
• 分子量: 171.244
• InChiKey: ZWNPUELCBZVMDA-NQHNDPCYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.69
• 重原子数：
  12.0
• 可旋转键数：
  6.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  4-(1-hexyn-1-yl)acetophenone 在 二甲基苯基硅烷 、 重水 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成 (Z)-methyl non-2-enoate 、 (Z)-methyl non-2-enoate
  参考文献：
  名称：

  Nanoporous Gold Catalyst for Highly Selective Semihydrogenation of Alkynes: Remarkable Effect of Amine Additives

  摘要：

  We report for the first time the highly selective semihydrogenation of alkynes using the unsupported nanoporous gold (AuNPore) as a catalyst and organosilanes with water as a hydrogen source. Under the optimized reaction conditions, the present semihydrogenation of various terminal- and internal-alkynes affords the corresponding alkenes in high chemical yields and excellent Z-selectivity without any, over-reduced alkanes. The use of DMF as solvent, which generates amines in situ, or pyridine as an additive is crucial to suppress the association of hydrogen atoms on AuNPore to form H-2 gas, which is unable to reduce alkynes on the unsupported gold catalysts. The AuNPore catalyst can be readily recovered and reused without any loss of catalytic activity. In addition, the SEM and TEM characterization of nanoporosity show that the AuNPore catalyst has a bicontinuous 3D structure and a high density of atomic steps and kinks on ligament surfaces, which should be one of the important origins of catalytic activity.

  DOI：

  10.1021/ja3087592

文献信息

• A Palladium Nanoparticle-Nanomicelle Combination for the Stereoselective Semihydrogenation of Alkynes in Water at Room Temperature
  作者：Eric D. Slack、Christopher M. Gabriel、Bruce H. Lipshutz

  DOI：10.1002/anie.201407723

  日期：2014.12.15

  The addition of NaBH4 to Pd(OAc)2 in water containing nanomicelles leads to the generation of H2 and Pd nanoparticles. Subsequent reduction of disubstituted alkynes affords Z‐alkenes in high yields. These reactions are general, take place in water at ambient temperatures, and offer recycling of the aqueous reaction mixture along with low overall E Factors.

  在含有纳米胶束的水中将NaBH 4 添加到Pd(OAc) 2导致H 2和Pd纳米颗粒的产生。随后二取代炔烃的还原以高产率提供Z-烯烃。这些反应是一般的，在环境温度下在水中发生，并且提供水性反应混合物的循环以及低的总 E 因子。