methyl (E)-4-cyclohexyl-4-hydroxybut-2-enoate | 516472-44-9

• 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: methyl (E)-4-cyclohexyl-4-hydroxybut-2-enoate
• CAS: 516472-44-9
• 化学式: C₁₁H₁₈O₃
• 分子量: 198.262
• InChiKey: VGLHFHFBVIUVDH-BQYQJAHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl (E)-4-cyclohexyl-4-hydroxybut-2-enoate 在 奎宁环 、 [Ir(dF(CF₃)ppy)₂(dtbbpy)](PF₆) 、 四丁基磷酸氢铵 作用下， 以 乙腈 为溶剂， 反应 48.0h， 以67%的产率得到4-环己基-4-氧代丁酸甲酯
  参考文献：
  名称：

  通过CH键活化对高取代的烯丙醇进行光氧化还原催化的异构化。

  摘要：

  γ-羰基取代的烯丙醇的光氧化还原催化异构化为其相应的羰基化合物是首次通过CH键进行活化。这种催化的氧化还原中性过程导致了1,4-二羰基化合物的合成。值得注意的是，带有四取代烯烃的烯丙基醇也可以转化成它们相应的羰基化合物。密度泛函理论计算表明，烯丙醇的γ位上的羰基有利于形成具有较高垂直电子亲和力的相应烯丙基醇自由基，这有助于完成光氧化还原催化循环。

  DOI：

  10.1002/anie.202000743
• 作为产物：
  描述：

  methyl 4-cyclohexyl-4-hydroxy-but-2-ynoate 在 红铝 、 盐酸 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 0.33h， 以80%的产率得到methyl (E)-4-cyclohexyl-4-hydroxybut-2-enoate
  参考文献：
  名称：

  Trans-Selective Conversions of γ-Hydroxy-α,β-Alkynoic Esters to γ-Hydroxy-α,β-Alkenoic Esters

  摘要：

  gamma-Hydroxy-alpha,beta-acetylenic esters are used as precursors to prepare gamma-hydroxy-alpha,beta-alkenoic esters by means of trans-selective additions of two hydrogen atoms or one hydrogen atom and one iodine atom across the triple bonds. These methods allow for the preparation of beta-substituted and alpha,beta-disubstituted alkenoic esters in highly stereoselective manners.

  DOI：

  10.1021/ol0495366

文献信息

• A general method for the preparation of 2,3,5-trisubstituted-furo[3,2-b]pyridines
  作者：Brian M Mathes、Sandra A Filla

  DOI：10.1016/s0040-4039(02)02655-2

  日期：2003.1

  The preparation of 2,3,5-trisubstituted-furo[3,2-b]pyridines via a Pd(0)-catalyzed intramolecular cyclization of methyl 4-(6-chloro-2-iodopyridin-3-yloxy)-substituted-butenoates 9a-f is described. This approach was both efficient and general, and provided the highly functionalized heterocyclic ring system in high yield. Among the several examples provided is the preparation of 3-[2-(N,N-dimethylamino)ethyl]-5-(4-fluorobenzoyl)amino-2-methylfuro[3,2-b]pyridine 4, a selective 5-HTIF receptor agonist. (C) 2003 Elsevier Science Ltd. All rights reserved.
• A novel and simple method to prepare γ-hydroxy-α,β-(E)-alkenoic esters from γ-keto-alkynoic esters
  作者：Tadaatsu Naka、Kazunori Koide

  DOI：10.1016/s0040-4039(02)02602-3

  日期：2003.1

  A method to convert gamma-keto-alkynoic esters to gamma-hydroxy-alpha,beta-(E)-alkenoic esters is described. This functional group transformation was accomplished in one step by means of NaBH, reduction in methanol. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Photoredox‐Catalyzed Isomerization of Highly Substituted Allylic Alcohols by C−H Bond Activation
  作者：Kai Guo、Zhongchao Zhang、Anding Li、Yuanhe Li、Jun Huang、Zhen Yang

  DOI：10.1002/anie.202000743

  日期：2020.7.6

  Photoredox‐catalyzed isomerization of γ‐carbonyl‐substituted allylic alcohols to their corresponding carbonyl compounds was achieved for the first time by C−H bond activation. This catalytic redox‐neutral process resulted in the synthesis of 1,4‐dicarbonyl compounds. Notably, allylic alcohols bearing tetrasubstituted olefins can also be transformed into their corresponding carbonyl compounds. Density

  γ-羰基取代的烯丙醇的光氧化还原催化异构化为其相应的羰基化合物是首次通过CH键进行活化。这种催化的氧化还原中性过程导致了1,4-二羰基化合物的合成。值得注意的是，带有四取代烯烃的烯丙基醇也可以转化成它们相应的羰基化合物。密度泛函理论计算表明，烯丙醇的γ位上的羰基有利于形成具有较高垂直电子亲和力的相应烯丙基醇自由基，这有助于完成光氧化还原催化循环。
• Trans-Selective Conversions of γ-Hydroxy-α,β-Alkynoic Esters to γ-Hydroxy-α,β-Alkenoic Esters
  作者：Christopher T. Meta、Kazunori Koide

  DOI：10.1021/ol0495366

  日期：2004.5.1

  gamma-Hydroxy-alpha,beta-acetylenic esters are used as precursors to prepare gamma-hydroxy-alpha,beta-alkenoic esters by means of trans-selective additions of two hydrogen atoms or one hydrogen atom and one iodine atom across the triple bonds. These methods allow for the preparation of beta-substituted and alpha,beta-disubstituted alkenoic esters in highly stereoselective manners.