oct-6-yn-2-ol | 24395-07-1

• 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: oct-6-yn-2-ol
• 英文别名: 6-octyn-2-ol；Octin-(6)-ol-(2)；6-Octin-2-ol
• CAS: 24395-07-1
• 化学式: C₈H₁₄O
• 分子量: 126.199
• InChiKey: JRISGDGERCSDQJ-UHFFFAOYSA-N

物化性质

• 熔点：
  -39°C (estimate)
• 沸点：
  204.35°C (rough estimate)
• 密度：
  0.8537 (estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 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：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  oct-6-yn-2-ol 在 正丁基锂 、 仲丁基锂 作用下， 生成 8-(trimethylsilyl)-6-octyn-2-yl tosylate
  参考文献：
  名称：

  Propargylsilane and (trimethylsilyl)alkyne terminator groups. Formation of an exocyclic allene in the acetolysis of 8-(trimethylsilyl)-6-octyn-2-yl tosylate

  摘要：

  DOI：

  10.1021/ja00535a062
• 作为产物：
  描述：

  丁位己内酯 在 三苯基膦 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 4.0h， 生成 oct-6-yn-2-ol
  参考文献：
  名称：

  一种制备非末端炔烃的新方法：在Tulearin A和C的总合成中的应用

  摘要：

  已知内酯会以Wittig型方式与CCl 4和PPh 3原位生成的试剂反应，生成宝石二氯烯烃衍生物。现已证明此类化合物在用有机锂试剂RLi处理后会发生还原烷基化反应，从而提供在其末端带有R取代基的乙炔衍生物（R = Me，n-，仲-，叔烷基，甲硅烷基）；该反应可以用Cu（acac）2或Fe（acac）3催化/ 1,2-二氨基苯 从容易获得的内酯前体以这种方式制备的两种炔醇衍生物，是细胞毒性海洋大环内酯类鹅膏蛋白A（1）和C（2）的总合成的关键组成部分。这些易碎目标的组装取决于闭环炔烃复分解（RCAM），然后通过反式氢化硅烷化/原去甲硅烷基化对所得的环炔烃进行正式的反式还原。

  DOI：

  10.1002/chem.201404873

文献信息

• Total Synthesis of Tulearin C
  作者：Konrad Lehr、Ronaldo Mariz、Lucie Leseurre、Barbara Gabor、Alois Fürstner

  DOI：10.1002/anie.201106117

  日期：2011.11.25

  alkyne metathesis will always be the little brother of alkene metathesis, it allows problems to be solved that are currently beyond reach of the more famous sibling. This notion is exemplified by the tulearin macrolides, which could only be selectively forged by ring‐closing alkyne metathesis (RCAM)/trans reduction using the latest generation of alkyne metathesis catalysts.

  在较小的兄弟的帮助下：尽管炔烃复分解将永远是烯烃复分解的小兄弟，但它可以解决当前更著名的同胞无法解决的问题。牛油蛋白大环内酯类是该概念的例证，其只能通过 使用最新一代炔烃复分解催化剂进行闭环炔烃复分解（RCAM）/反式还原来选择性地伪造。
• Asymmetric Synthesis of Bicyclic Ketones Having an Angular Substituent via Ti(II) Alkoxide-Mediated Tandem Cyclization of Trisubstituted Olefinic Substrates
  作者：Hirokazu Urabe、Daigaku Hideura、Fumie Sato

  DOI：10.1021/ol9904038

  日期：2000.2.1

  [reaction: see text] Angularly substituted, optically active bicyclic ketones of up to 94% ee were prepared by the Ti(II) alkoxide-mediated tandem cyclization of open-chain substrates, that is, 8-phenylmenthyl enynoates having a trisubstituted double bond.

  [反应：参见正文]通过Ti（II）醇盐介导的开链底物的串联环化反应制备了高达94％ee的角取代的旋光双环酮，即具有三取代双键的8-苯基薄荷基烯酸酯。
• Hydrogenation Promoter, Hydrogenation Catalyst, and Process for Producing Alkene Compound
  申请人：Hori Junichi

  公开号：US20080033221A1

  公开（公告）日：2008-02-07

  A hydrogenation promoter of the present invention is produced by reacting an alkyne compound or an alkene compound, a palladium compound represented by a general formula Pd(II)X j L k (where L represents a monodentate ligand or a polydendate ligand other than a phosphorus-containing ligand (when two or more Ls are present in the compound, the Ls may be the same or different), X represents an anionic group, j represents a value determined according to the valence of X so that X j has a valence of −2 as a whole, and k represents an integer in the range of 0 to 4), and a base in an organic solvent. Specifically, The hydrogenation promoter of the invention includes palladium nanoparticles containing the alkyne compound or the alkene compound as an agglomeration-preventing agent.

  本发明的氢化促进剂是通过在有机溶剂中反应炔烃化合物或烯烃化合物、由一般式Pd(II)XjLk表示的钯化合物(其中L表示单齿配体或不含磷的多齿配体（当化合物中存在两个或两个以上的L时，L可以相同也可以不同），X表示阴离子基团，j表示根据X的价确定的值，使Xj整体价为-2，k表示0到4之间的整数)，以及碱的反应产生的。具体来说，本发明的氢化促进剂包括含有炔烃化合物或烯烃化合物作为凝聚抑制剂的钯纳米粒子。
• Solvents of low nucleophilicity. XII. Triple-bond participation in the acetolysis, formolysis, and trifluoroacetolysis of 6-heptyn-2-yl tosylate and 6-octyn-2-yl tosylate
  作者：Paul E. Peterson、Rajaninath J. Kamat

  DOI：10.1021/ja01044a035

  日期：1969.7
• Catalytic Cycloisomerization of Unsaturated Organoiodides
  作者：William F. Bailey、Matthew W. Carson

  DOI：10.1021/jo981991q

  日期：1998.12.1

  Catalytic quantities of phenyllithium (PhLi) have been found to initiate novel 5-exo cycloisomerization of a variety of structurally diverse unsaturated organoiodides. The isomerization reaction appears to be a process of broad synthetic utility for the preparation of iodomethyl-substituted five-membered rings. Primary, secondary, tertiary, or aryl iodides tethered to a suitably positioned carbon-carbon pi-bond are converted cleanly to their cyclic isomers in good to excellent yield (i.e., 70-90%) by simply allowing a hydrocarbon-MTBE solution of the iodide to stand in the presence of a small quantity of PhLi at an appropriate temperature. The mechanism of the cycloisomerization was found to be substrate dependent: unsaturated aryl and primary alkyl iodides undergo isomerization via a three-step cascade (eqs 1-3) mediated by two reversible lithium-iodine exchange reactions bracketing an irreversible 5-exo cyclization of an unsaturated organolithium; unsaturated secondary and tertiary alkyl iodides apparently isomerize via a radical-mediated atom transfer process initiated by homolytic fragmentation of the ate-complex generated upon attack of PhLi on the iodine atom of the substrate.