6-octynoic acid methyl ester | 105105-62-2

• 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: 6-octynoic acid methyl ester
• 英文别名: methyl 7-methyl-6-heptynate；oct-6-ynoic acid methyl ester；Oct-6-insaeure-methylester；Methyl oct-6-ynoate
• CAS: 105105-62-2
• 化学式: C₉H₁₄O₂
• 分子量: 154.209
• InChiKey: HVGJJUDMAHFQNX-UHFFFAOYSA-N

物化性质

• 沸点：
  193.0±23.0 °C(Predicted)
• 密度：
  0.940±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-octynoic acid methyl ester 在 四甲基乙二胺 、 potassium carbonate 、 三氟乙酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 为溶剂， 反应 40.25h， 生成 6-hept-5-ynyl-4-hydroxypyran-2-one
  参考文献：
  名称：

  Study towards bioactive pyrone derivatives from the marine red alga Phacelocarpus labillardieri

  摘要：

  Red algae of the genus Phacelocarpus labillardieri produce a structurally rather unique class of macrocyclic pyrone derivatives with phospholipase A, inhibiting properties and potential neuromuscular blocking activity. They were also shown to be potent feeding inhibitors for various marine herbivorous gastropods. Described herein is the first preparative study towards these conspicuous secondary metabolites. Their carbon skeleton has been assembled in a few straightforward steps using ring closing alkyne metathesis (RCAM) catalyzed by the Schrock alkylidyne complex (tBuO)(3)WdropCCMe(3) to forge the meta-cyclophane core with high efficiency. (C) 2003 Elsevier Ltd. All fights reserved.

  DOI：

  10.1016/s0040-4020(03)00815-9
• 作为产物：
  描述：

  6-庚炔酸 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 正戊烷 为溶剂， 反应 12.0h， 生成 6-octynoic acid methyl ester
  参考文献：
  名称：

  Study towards bioactive pyrone derivatives from the marine red alga Phacelocarpus labillardieri

  摘要：

  Red algae of the genus Phacelocarpus labillardieri produce a structurally rather unique class of macrocyclic pyrone derivatives with phospholipase A, inhibiting properties and potential neuromuscular blocking activity. They were also shown to be potent feeding inhibitors for various marine herbivorous gastropods. Described herein is the first preparative study towards these conspicuous secondary metabolites. Their carbon skeleton has been assembled in a few straightforward steps using ring closing alkyne metathesis (RCAM) catalyzed by the Schrock alkylidyne complex (tBuO)(3)WdropCCMe(3) to forge the meta-cyclophane core with high efficiency. (C) 2003 Elsevier Ltd. All fights reserved.

  DOI：

  10.1016/s0040-4020(03)00815-9

文献信息

• Indirect Electroreductive Sequential Radical Reaction Catalyzed by a Ni(II) Complex. One-Step Preparation of Functionalized (Methylene)cyclopentanes.
  作者：Shigeko OZAKI、Shizue MITOH、Hidenobu OHMORI

  DOI：10.1248/cpb.43.1435

  日期：——

  Substituted (methylene)cyclopentanes were prepared by one-step reaction at room temperature from butynyl iodides and activated olefins by sequencing of free radical addition and cyclization reactions. The reactions, which were conducted by indirect electroreduction catalyzed by a nickel(II) complex, proceeded with modest selectivity for formation of the Z(methylene)cyclopentanes.

  通过一步反应，在室温下利用丁炔基碘和活化烯烃，通过自由基加成和环化反应的序列，制备了取代的(methylene)环戊烷。这些反应是在镍(II)配合物催化下进行的间接电还原反应，形成Z(methylene)环戊烷时具有适度的选择性。
• Cobalt-Catalyzed Regio- and Stereoselective Hydrosilylation of Alk-2-ynes with Tertiary Silanes
  作者：Hongfang Li、Chengbo Yang、Dongyang Wang、Liang Deng

  DOI：10.1021/acs.organomet.2c00563

  日期：——

  Selectivity control in the addition reactions of internal alkynes that bear two similar substituents presents a big challenge in modern organic synthesis. Herein we report that β-(E)-selective hydrosilylation of alk-2-ynes with tertiary silanes can be achieved by using Co2(CO)8 as the catalyst. Under the catalytic reaction conditions, a wide range of alk-2-ynes can be converted into vinylsilanes with

  带有两个相似取代基的内部炔烃加成反应的选择性控制对现代有机合成提出了巨大的挑战。在此我们报道了通过使用Co 2 (CO) 8作为催化剂可以实现烷-2-炔与叔硅烷的β-( E )-选择性氢化硅烷化。在催化反应条件下，多种烷-2-炔可以转化为乙烯基硅烷，其中β-( E )异构体作为主要或唯一的氢化硅烷化产物。机理研究表明炔桥二钴物质是可能的中间体。烯基桥联二钴甲硅烷基中间体中取代基之间的空间排斥被认为是引起观察到的区域选择性的关键因素。
• Relay Catalysis for Selective Aerobic Oxidative Esterification of Primary Alcohols with Methanol
  作者：Yibo Yu、Jie Lin、Anni Qin、Huanan Wang、Jie Wang、Weiyi Wang、Guolin Wu、Qian Zhang、Hui Qian、Shengming Ma

  DOI：10.1021/acs.orglett.4c01059

  日期：2024.4.26

  and ubiquitous in polymers, bioactive compounds, and natural products. Their traditional synthetic approach is the esterification of carboxylic acids or their activated derivatives with alcohols. Herein, a bimetallic relay catalytic protocol was developed for the aerobic esterification of one alcohol in the presence of a slowly oxidizing alcohol, which has been identified as methanol. A concise synthesis

  酯是大宗化学品和精细化学品，普遍存在于聚合物、生物活性化合物和天然产品中。他们的传统合成方法是羧酸或其活化衍生物与醇的酯化。在此，开发了一种双金属中继催化方案，用于在缓慢氧化的醇（已被鉴定为甲醇）存在下对一种醇进行有氧酯化。进行了邻苯酸的简明合成以证明该反应的实用性和潜力。
• 10.1002/chem.202401815
  作者：Zhang, Qian、Zhang, Jiabin、Qian, Hui、Ma, Shengming

  DOI：10.1002/chem.202401815

  日期：——

  With Fe(NO3)3 ⋅ 9H2O and TEMPO as cocatalysts and oxygen as green oxidant, PMB ethers have been converted to carboxylic acids at room temperature with high efficiency and selectivity. Total synthesis of naturally occuring (R)-6-hydroxy-7,9-octadecadiynoic acid has been realized by applying this protocol as key step. A mechanism involving oxygen-stabilized benzylic cation has been proposed based on

  以 Fe（NO3）3 ⋅ 9H2O 和 TEMPO 为助催化剂，以氧为绿色氧化剂，PMB 醚在室温下以高效率和选择性转化为羧酸。通过将该方案作为关键步骤，已经实现了天然存在的 （R）-6-羟基-7,9-十八烷二炔酸的完全合成。基于仔细研究，已经提出了一种涉及氧稳定苄基阳离子的机制。
• Newman; Wotiz, Journal of the American Chemical Society, 1949, vol. 71, p. 1294
  作者：Newman、Wotiz

  DOI：——

  日期：——