undec-1-en-6-yn-5-ol | 158044-44-1

• 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: undec-1-en-6-yn-5-ol
• CAS: 158044-44-1
• 化学式: C₁₁H₁₈O
• 分子量: 166.263
• InChiKey: MGSPSGUOKOFVRN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  12
• 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：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  undec-1-en-6-yn-5-ol 在 咪唑 、 bis(cyclopentadienyl)bis(trimethylphosphane)titanium(II) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 20.05h， 生成
  参考文献：
  名称：

  Development of a Titanocene-Catalyzed Enyne Cyclization/Isocyanide Insertion Reaction

  摘要：

  The first early transition metal-catalyzed enyne cyclization reaction is described. The system converts enyne substrates to bicyclic iminocyclopentenes through the use of 10 mol % of Cp(2)Ti(PMe(3))(2) in the presence of a silyl cyanide. Subsequent hydrolysis produces the corresponding bicyclic cyclopentenones in good overall yield. The cyclization reaction is tolerant of polar functional groups such as ethers, amines, and esters and is diastereoselective with certain chiral enyne substrates.

  DOI：

  10.1021/ja00098a020
• 作为产物：
  描述：

  4-戊烯醛 、 1-己炔 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.66h， 生成 undec-1-en-6-yn-5-ol
  参考文献：
  名称：

  Highly enantioselective addition of linear alkyl alkynes to linear aldehydes

  摘要：

  It is discovered that the use of biscyclohexylamine (Cy(2)NH) as an additive can greatly enhance the enantioselectivity for the reaction of linear alkyl alkynes with linear aldehydes. The combination of (S)-BINOL (20 mol %), Cy(2)NH (5 mol %), ZnEt(2) (2 equiv), and Ti(O(i)Pr)(4) (0.5 equiv) catalyzes the reaction at room temperature in diethyl ether solution with 81-89% ee and 57-77% yield. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.07.082

文献信息

• A gold(i)-catalyzed intramolecular oxidation–cyclopropanation sequence of 1,6-enynes: a convenient access to [n.1.0]bicycloalkanes
  作者：Deyun Qian、Junliang Zhang

  DOI：10.1039/c1cc14788a

  日期：——

  A gold(I)-catalyzed tandem oxidation/cyclopropanation reaction of 1,6-enynes with an external oxidant has been developed. This quite simple and rapid strategy will provide a safe, mild and versatile avenue to numerous carbo- and hetero [n.1.0]bicyclic frameworks.

  已经开发了金（I）催化的1，6-炔烃与外部氧化剂的串联氧化/环丙烷化反应。这种非常简单，快速的策略将为众多碳和杂[n.1.0]双环框架提供安全，温和且通用的途径。
• Catalytic Asymmetric Synthesis of Chiral Propargylic Alcohols for the Intramolecular Pauson−Khand Cycloaddition
  作者：Mark Turlington、Yang Yue、Xiao-Qi Yu、Lin Pu

  DOI：10.1021/jo101545v

  日期：2010.10.15

  aldehydes are used to prepare the propargylic alcohol-based chiral en-ynes. Protection of the propargylic alcohols with either an acetyl or a methyl group allows the resulting en-ynes to undergo the intramolecular Pauson−Khand reaction to form the corresponding optically active 5,5- and 5,6-fused bicyclic products with high diastereoselectivity and high enantiomeric purity. In the major product, the propargylic

  用于将醛催化不对称炔烃加成醛的几种方法用于制备基于炔丙醇的手性烯炔。用乙酰基或甲基保护炔丙醇可以使所产生的烯炔分子内发生Pauson-Khand反应，形成具有高非对映选择性和高非对映活性的5,5-和5,6-稠合双环产物对映体纯度。在主要产物中，炔丙基取代基和桥头氢在稠合双环上相对于彼此是顺式的。由不对称炔烃加成产生的炔丙醇的对映体纯度在环加成产物中得以保持。制备手性炔丙醇的烯丙基醚，其还可以进行高度非对映选择性的Pauson-Khand环加成，并保留高对映体纯度。这项研究表明，炔丙基位置以及炔烃上取代基的大小对于非对映选择性很重要，取代基的体积越大，非对映选择性就越高。
• Complex α-Pyrones Synthesized by a Gold-Catalyzed Coupling Reaction
  作者：Tuoping Luo、Stuart L. Schreiber

  DOI：10.1002/anie.200703276

  日期：2007.11.5
• PtCl₂-Catalyzed Rapid Access to Tetracyclic 2,3-Indoline-Fused Cyclopentenes:  Reactivity Divergent from Cationic Au(I) Catalysis and Synthetic Potential
  作者：Guozhu Zhang、Vincent J. Catalano、Liming Zhang

  DOI：10.1021/ja074536x

  日期：2007.9.1

  A PtCl2-catalyzed 3,3-rearrangement/[3+2]-cycloaddition of propargylic 3-indoleacetates is developed. Besides the efficient formation of highly functionalized tetracyclic cyclopentenes, the reaction is dramatically divergent from that catalyzed by cationic Au-I. Moreover, the synthetic potential of this method is demonstrated by a succinct synthesis of the tetracyclic core of vindolinine.
• Berk Scott C., Grossman Robert B., Buchwald Stephen L., J. Amer Chem. Soc, 116 (1994) N 19, S 8593-8601
  作者：Berk Scott C., Grossman Robert B., Buchwald Stephen L.

  DOI：——

  日期：——