5-cyclohexylidenepentanoic acid methyl ester | 503868-31-3

• 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: 5-cyclohexylidenepentanoic acid methyl ester
• 英文别名: methyl 5-cyclohexylidenepentanoate
• CAS: 503868-31-3
• 化学式: C₁₂H₂₀O₂
• 分子量: 196.29
• InChiKey: ALGAKGXZDRGJLZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 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：

  5-cyclohexylidenepentanoic acid methyl ester 在 吡啶 、 lithium aluminium tetrahydride 、 三乙胺 、 三氯氧磷 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 生成 5-Cyclohexylidenepentyl 2-(1-methylpiperidin-1-ium-1-yl)ethyl phosphate
  参考文献：
  名称：

  Antileishmanial Ring-Substituted Ether Phospholipids

  摘要：

  Three series of ring-substituted ether phospholipids were synthesized carrying N,N,N-trimethylammonium, N-methylpiperidino, or N-methylmorpholino headgroups. The first series is substituted by 2-cyclohexyloxyethyl or 2-(4-alkylidenecyclohexyloxy)ethyl groups, the second series by cyclohexylidenealkyl or adamantylidenealkyl moieties, and the third series by 2-aryloxyethyl or 6-aryloxyhexyl groups in the alkyl portion of the molecule. The antileishmanial activity of the new compounds was evaluated in vitro against the promastigote forms of L. donovani and L. infantum using an MTT (3-(4,5-dimethylthiazol-2yl)-2,5-diphenyltetrazolium bromide)-based microassay as a marker of cell viability. Analogues 12, 15, 24, 30, 32, 41, 43, and 45 were more potent than the control compound miltefosine (hexadecylphosphocholine) against both L. donovani and L. infantum while, derivatives 13 and 42 were equipotent to miltefosine. Analogues 16, 17, 19, 20 were more potent than miltefosine against L. infantum and compounds 27, 31, 44 were more active than miltefosine against L. donovani. Differential scanning calorimetry (DSC) was used to probe the role of individual ether phospholipids on the physicochemical properties of model membranes. The DSC scans showed that the active compounds have a more profound effect on the thermotropic properties of model membrane bilayers than the less active ones.

  DOI：

  10.1021/jm020972c
• 作为产物：
  描述：

  4-羧丁基三苯基溴化膦 在 硫酸 、 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 为溶剂， 反应 6.25h， 生成 5-cyclohexylidenepentanoic acid methyl ester
  参考文献：
  名称：

  Antileishmanial Ring-Substituted Ether Phospholipids

  摘要：

  Three series of ring-substituted ether phospholipids were synthesized carrying N,N,N-trimethylammonium, N-methylpiperidino, or N-methylmorpholino headgroups. The first series is substituted by 2-cyclohexyloxyethyl or 2-(4-alkylidenecyclohexyloxy)ethyl groups, the second series by cyclohexylidenealkyl or adamantylidenealkyl moieties, and the third series by 2-aryloxyethyl or 6-aryloxyhexyl groups in the alkyl portion of the molecule. The antileishmanial activity of the new compounds was evaluated in vitro against the promastigote forms of L. donovani and L. infantum using an MTT (3-(4,5-dimethylthiazol-2yl)-2,5-diphenyltetrazolium bromide)-based microassay as a marker of cell viability. Analogues 12, 15, 24, 30, 32, 41, 43, and 45 were more potent than the control compound miltefosine (hexadecylphosphocholine) against both L. donovani and L. infantum while, derivatives 13 and 42 were equipotent to miltefosine. Analogues 16, 17, 19, 20 were more potent than miltefosine against L. infantum and compounds 27, 31, 44 were more active than miltefosine against L. donovani. Differential scanning calorimetry (DSC) was used to probe the role of individual ether phospholipids on the physicochemical properties of model membranes. The DSC scans showed that the active compounds have a more profound effect on the thermotropic properties of model membrane bilayers than the less active ones.

  DOI：

  10.1021/jm020972c

文献信息

• Organoelectrocatalysis Enables Direct Cyclopropanation of Methylene Compounds
  作者：Liang-Hua Jie、Bin Guo、Jinshuai Song、Hai-Chao Xu

  DOI：10.1021/jacs.1c12762

  日期：2022.2.9

  electrocatalytic strategy for the cyclopropanation of active methylene compounds, employing an organic catalyst. The method shows a broad substrate scope and excellent scalability, requires no metal catalyst or external chemical oxidant, and provides convenient access to several types of cyclopropane-fused heterocyclic and carbocyclic compounds. Mechanistic investigations suggest that the reactions

  环丙烷是天然产物和生物活性化合物中普遍存在的结构单元。虽然过渡金属催化的烯烃环丙烷化功能化化合物（如 α-重氮羰基衍生物）已经很好地建立起来，并提供了直接获得环丙烷的途径，但直接从更稳定和更简单的亚甲基化合物进行环丙烷化仍然是一个未解决的挑战，尽管最小化具有非常理想的好处。预功能化和提高操作安全性。在此，我们报告了一种使用有机催化剂进行活性亚甲基化合物环丙烷化的电催化策略。该方法表现出广泛的底物范围和优异的可扩展性，不需要金属催化剂或外部化学氧化剂，并提供方便地访问几种类型的环丙烷稠合杂环和碳环化合物。机理研究表明，反应通过自由基-极性交叉过程进行，在新生的环丙烷环中形成两个新的碳-碳键。
• Antileishmanial Ring-Substituted Ether Phospholipids
  作者：Nikos Avlonitis、Eleni Lekka、Anastasia Detsi、Maria Koufaki、Theodora Calogeropoulou、Efi Scoulica、Eleni Siapi、Ioanna Kyrikou、Thomas Mavromoustakos、Andrew Tsotinis、Simona Golic Grdadolnik、Alexandros Makriyannis

  DOI：10.1021/jm020972c

  日期：2003.2.1

  Three series of ring-substituted ether phospholipids were synthesized carrying N,N,N-trimethylammonium, N-methylpiperidino, or N-methylmorpholino headgroups. The first series is substituted by 2-cyclohexyloxyethyl or 2-(4-alkylidenecyclohexyloxy)ethyl groups, the second series by cyclohexylidenealkyl or adamantylidenealkyl moieties, and the third series by 2-aryloxyethyl or 6-aryloxyhexyl groups in the alkyl portion of the molecule. The antileishmanial activity of the new compounds was evaluated in vitro against the promastigote forms of L. donovani and L. infantum using an MTT (3-(4,5-dimethylthiazol-2yl)-2,5-diphenyltetrazolium bromide)-based microassay as a marker of cell viability. Analogues 12, 15, 24, 30, 32, 41, 43, and 45 were more potent than the control compound miltefosine (hexadecylphosphocholine) against both L. donovani and L. infantum while, derivatives 13 and 42 were equipotent to miltefosine. Analogues 16, 17, 19, 20 were more potent than miltefosine against L. infantum and compounds 27, 31, 44 were more active than miltefosine against L. donovani. Differential scanning calorimetry (DSC) was used to probe the role of individual ether phospholipids on the physicochemical properties of model membranes. The DSC scans showed that the active compounds have a more profound effect on the thermotropic properties of model membrane bilayers than the less active ones.