(Z)-cyclooct-2-ene-1-carboxylic acid

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (Z)-cyclooct-2-ene-1-carboxylic acid
• 英文别名: 2-Cyclooctene-1-carboxylic acid；(2Z)-cyclooct-2-ene-1-carboxylic acid
• 化学式: C₉H₁₄O₂
• 分子量: 154.209
• InChiKey: NLLYUAGKSVKJEZ-XQRVVYSFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (Z)-cyclooct-2-ene-1-carboxylic acid 在 苯甲酸甲酯 、 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 48.0h， 生成 methyl (2E)-cyclooct-2-ene-1-carboxylate
  参考文献：
  名称：

  Bond-Breaking Bio-orthogonal Chemistry Efficiently Uncages Fluorescent and Therapeutic Compounds under Physiological Conditions

  摘要：

  Bond-breaking bio-orthogonal chemistry, consisting of a "click" reaction between trans-cyclooctene and tetrazine, followed by an intramolecular cyclization-driven uncaging step is described. The two-step process allows activation of caged compounds in biological media at neutral pH. The feasibility of this chemistry has been illustrated using NMR, while kinetics and pH-dependence were studied by fluorescence spectroscopy using caged coumarin. The practicality of the strategy is illustrated by activation of an anticancer drug, etoposide.

  DOI：

  10.1021/acs.orglett.0c02129
• 作为产物：
  描述：

  1-hydroxy-cyclooctanecarbonitrile 在 sodium hydroxide 、 氯化亚砜 作用下， 生成 (Z)-cyclooct-2-ene-1-carboxylic acid
  参考文献：
  名称：

  Braidy,R., Bulletin de la Societe Chimique de France, 1967, # 9, p. 3489 - 3495

  摘要：

  DOI：

文献信息

• Synthesis of Sequence-Specific Polymers with Amide Side Chains via Regio-/Stereoselective Ring-Opening Metathesis Polymerization of 3-Substituted <i>cis</i>-Cyclooctene
  作者：Kohei Osawa、Shingo Kobayashi、Masaru Tanaka

  DOI：10.1021/acs.macromol.6b01829

  日期：2016.11.8

  (trans-head-to-tail) polymers with amide side chains on every eighth backbone carbon were successfully synthesized by ring-opening metathesis polymerization (ROMP) of 3-substituted cis-cyclooctene (3RCOE) using Grubbs second-generation catalyst (G2). Regioregular linear ethylene–acrylamide copolymers were also prepared via hydrogenation of the obtained poly(3RCOE)s. The thermal properties and solubility

  通过使用Grubbs第二种方法通过3-取代的顺式环辛烯（3RCOE）的开环易位聚合（ROMP），成功合成了每八个主链碳上带有酰胺侧链的高度区域/立体规整的反式/头尾型聚合物。生成催化剂（G2）。还通过氢化所获得的聚（3RCOE）s来制备区域规则的线性乙烯-丙烯酰胺共聚物。所得聚合物的热性质和溶解性受到侧链中酰胺氢的存在，碳主链中不饱和键的存在以及侧链密度的强烈影响。侧链中酰胺氢的存在导致结晶聚合物的形成，以及这些聚合物在普通有机溶剂中的溶解度不足。相反，在侧链中不存在酰胺氢导致形成无定形聚合物，该聚合物在普通有机溶剂中具有良好的溶解性，并且T g值降低 通过氢化使主链中的双键饱和，观察到无定形聚合物。
• [EN] ORGANIC COMPOUNDS<br/>[FR] COMPOSÉS ORGANIQUES
  申请人：GIVAUDAN SA

  公开号：WO2019219743A1

  公开（公告）日：2019-11-21

  The present invention relates to ethyl cyclooct-3/4-ene-1-carboxylates, and to a process of making the same. The invention further refers to flavour and fragrance compositions comprising them.

  本发明涉及乙基环辛-3/4-烯-1-羧酸酯，以及制备该化合物的方法。该发明还涉及包含这些化合物的风味和香料组合物。
• Synthesis of β,γ-Unsaturated Aliphatic Acids via Ligand-Enabled Dehydrogenation
  作者：Tao Sheng、Guowei Kang、Zhe Zhuang、Nikita Chekshin、Zhen Wang、Liang Hu、Jin-Quan Yu

  DOI：10.1021/jacs.3c06423

  日期：2023.9.27

  α,β-Dehydrogenation of aliphatic acids has been realized through both enolate and β-C–H metalation pathways. However, the synthesis of isolated β,γ-unsaturated aliphatic acids via dehydrogenation has not been achieved to date. Herein, we report the ligand-enabled β,γ-dehydrogenation of abundant and inexpensive free aliphatic acids, which provides a new synthetic disconnection as well as a versatile

  脂肪酸的α,β-脱氢是通过烯醇化和β-C-H金属化途径实现的。然而，迄今为止，通过脱氢合成分离的β,γ-不饱和脂肪酸尚未实现。在此，我们报道了丰富且廉价的游离脂肪酸的配体启用的β，γ-脱氢，这提供了一种新的合成断开以及复杂分子在远程γ位点的下游功能化的通用平台。各种游离脂肪酸，包括环尺寸从五元到大环的无环和环状系统，都可以进行有效的脱氢。值得注意的是，该方案在存在更容易接近的 α-C-H 键的情况下具有良好的化学选择性，并且在融合双环支架中具有出色的区域选择性。该协议的实用性已通过一系列生物活性萜烯天然产物在 γ 位点的后期功能化得到证明。 β,γ-双键的进一步功能化允许将共价弹头（包括环氧化物、氮丙啶和β-内酯）安装到复杂的天然产物支架中，这对于靶向共价药物的发现很有价值。
• Synthesis of unsaturated acids by 1,2-addition of formic acid to conjugated dienes catalyzed by palladium on carbon in the presence of mono and bidentate phosphines
  作者：Giuseppe Vasapollo、Anoma Somasunderam、Bassam El Ali、Howard Alper

  DOI：10.1016/s0040-4039(00)73391-0

  日期：1994.8

  Di-, and trisubstituted 1,3-dienes are converted to gamma,delta-unsaturated acids by use of formic acid, carbon monoxide, and catalytic quantities of Pd-C/PPh(3)/Ph(2)P(CH2)(4)PPh(2) in 1,2-dimethoxyethane. A beta,gamma-unsaturated acid was obtained when the monosubstituted diene, isoprene, was used as the reactant.
• Ein neuartiger ligandentyp zur CC-verknüpfung von Cycloalkenen mit CO2 am (Lig) Ni(0-System, folgereaktionen
  作者：Heinz Hoberg、Alfredo Ballesteros、Andrei Sigan

  DOI：10.1016/0022-328x(91)83112-h

  日期：1991.2

  Cyclooctene reacts with CO2 on the (Lig)Ni0-system I [Lig = ((c)C6H11)2PCH2CH2-2-Pyridyl] to form the bicyclic complex IV containing a five-membered ring unit. Protonolysis of this complex with Et2O/HC1 yields quantitatively cyclooctyl carboxylic acid V, while treatment with dilute inorganic acids causes a sequence of reactions to occur which lead to the formation of beta-gamma-unsaturated cyclooctenyl carboxylic acid VI (92%).