1-hexenyl ethyl zinc

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: 1-hexenyl ethyl zinc
• 化学式: C₈H₁₆Zn
• 分子量: 177.605
• InChiKey: GBMOHZIFBFLUDX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.21
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 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-hexenyl ethyl zinc 在 三氟化硼乙醚 、 臭氧 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 2,2-Dimethyl-propionic acid (R)-1-((R)-2-hydroxy-butyl)-heptyl ester
  参考文献：
  名称：

  Anti-1,3-diols by Addition of Dialkylzinc Reagents to 4-Acetoxy-1,3-dioxanes

  摘要：

  Dialkylzincs couple with 4-acetoxy-6-alkyl-1,3-dioxanes in the presence of trimethylsilyl triflate (TMSOTf) to form trans-4,6-dialkyl-1,3-dioxanes with excellent diastereoselectivities. These dioxanes could be deprotected to yield anti-1,3-diols. A variety of functional groups are tolerated in the dialkylzinc, although silyl and benzyl ethers led to diminished diastereoselectivities. Substituents at the C5-position of the dioxane ring have little effect on the selectivity, while small C2 (acetal) substituents led to slightly reduced diastereoselectivity. These couplings work best with cyclic acetals, which can be difficult to hydrolyze. The 4-(benzyloxy)butanal (BOB) acetal has been developed as a new cyclic acetal protecting group that is compatible with dialkylzinc coupling reactions. BOB protecting groups are easily removed by catalytic hydrogenation followed by mild acid hydrolysis.

  DOI：

  10.1021/jo982264y

文献信息

• Solid-Phase Synthesis of Chiral <i>N</i>-Acylethylenediamines and Their Use as Ligands for the Asymmetric Addition of Alkylzinc and Alkenylzinc Reagents to Aldehydes
  作者：Christopher M. Sprout、Meaghan L. Richmond、Christopher T. Seto

  DOI：10.1021/jo049160+

  日期：2004.10.1

  synthesis of chiral N-acylethylenediamine ligands. The ligands are obtained in good yield and purity, without the need for chromatography or other purification methods. Several new and previously reported ligands were prepared using this procedure. These compounds were examined as catalysts for the enantioselective addition of alkylzinc reagents to aldehydes. In all cases, the crude ligands from the solid-phase

  已经开发了用于合成手性N-酰基乙二胺配体的固相方法。以良好的产率和纯度获得配体，而不需要色谱法或其他纯化方法。使用该程序制备了几种新的和先前报道的配体。检查了这些化合物作为将烷基锌试剂对映异构体加成到醛中的催化剂。在所有情况下，与使用已通过标准方法纯化的配体进行的反应相比，固相合成的粗配体以相似的收率和立体选择性催化反应。还对配体3a和3f进行了初步研究用作将烯基锌试剂加到醛中以得到手性烯丙基醇的催化剂。发现配体3f以高达76％的ee催化该加成反应。
• A General, Iterative, and Modular Approach toward Carbohydrate Libraries Based on Ruthenium-Catalyzed Oxidative Cyclizations
  作者：Meike Niggemann、Andreas Jelonek、Nicole Biber、Margarita Wuchrer、Bernd Plietker

  DOI：10.1021/jo801528n

  日期：2008.9.19

  the selective modular synthesis of natural and non-natural carbohydrates within five synthetic steps starting from readily available starting materials. Due to a sequential introduction of O- or N-functionalities, a regioselective protection of each new functional group is possible. The key step in the carbohydrate synthesis is a RuO4-catalyzed oxidative cyclization via a pH-dependent dehydrogenatio

  碳水化合物是一类无所不在的高氧天然产物。由于它们具有广泛的生物学活性，它们在合成有机化学的中心已经有130多年的历史了。在过去的50年中，非天然碳水化合物吸引了有机，生物和医学化学领域的各种化学家的兴趣。尤其是脱氧糖被证明是一类重要的化合物。迄今为止，大多数非天然类似物是在多步合成中从天然，对映体纯的碳水化合物开始合成的。在这份报告中，我们提出了一种合成策略，允许从容易获得的起始原料开始的五个合成步骤中，选择性地模块化合成天然和非天然碳水化合物。由于O功能或N功能的顺序引入，每个新功能基团的区域选择性保护都是可能的。碳水化合物合成中的关键步骤是通过pH依赖的脱氢-二羟基化-环化或氧化裂解-环化实现RuO4催化的氧化环化，从而产生高度取代的新碳水化合物，其中每个官能团均受到正交保护并可以进一步利用综合操作。
• Dialkylzinc Additions to 4-Acetoxy-1,3-dioxanes:  A Highly Stereoselective Route to Protected <i>anti</i>-1,3-Diols
  作者：Scott D. Rychnovsky、Noel A. Powell

  DOI：10.1021/jo971207m

  日期：1997.9.1
• Soai, Kenso; Takahashi, Kuniyoshi, Journal of the Chemical Society. Perkin transactions I, 1994, # 10, p. 1257 - 1258
  作者：Soai, Kenso、Takahashi, Kuniyoshi

  DOI：——

  日期：——
• Electroauxiliary-Assisted Sequential Introduction of Two Carbon Nucleophiles on the Same α-Carbon of Nitrogen:  Application to the Synthesis of Spiro Compounds
  作者：Seiji Suga、Mitsuru Watanabe、Jun-ichi Yoshida

  DOI：10.1021/ja028663z

  日期：2002.12.1

  The sequential introduction of two carbon nucleophiles on the same alpha-carbon of nitrogen by using selective oxidative cleavage of two silyl groups as electroauxilialies has been accomplished. The combination of this expedient transformation and ring-closing metathesis enables reliable and straightforward syntheses of nitrogen-containing spiro compounds, such as cephalotaxine.