(S)-(Cyclohex-2-en-1-yl) 4-methoxyphenyl ether | 175735-28-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (S)-(Cyclohex-2-en-1-yl) 4-methoxyphenyl ether
• 英文别名: (S)-cyclohex-2-enyl 4'-methoxyphenyl ether；1-[(1S)-cyclohex-2-en-1-yl]oxy-4-methoxybenzene
• CAS: 175735-28-1
• 化学式: C₁₃H₁₆O₂
• 分子量: 204.269
• InChiKey: GURXAIQCXXNSSO-GFCCVEGCSA-N

物化性质

• 沸点：
  308.7±35.0 °C(Predicted)
• 密度：
  1.057±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-(Cyclohex-2-en-1-yl) 4-methoxyphenyl ether 在 Eu(fod)3 作用下， 以 氯仿 为溶剂， 以79%的产率得到(R)-2'-(cyclohex-2-enyl)-4'-methoxyphenol
  参考文献：
  名称：

  Asymmetric O- and C-Alkylation of Phenols

  摘要：

  DOI：

  10.1021/ja972453i
• 作为产物：
  描述：

  2-Cyclohexenyl-p-anisylether 生成 (S)-(Cyclohex-2-en-1-yl) 4-methoxyphenyl ether
  参考文献：
  名称：

  Zirconium-Catalyzed Kinetic Resolution of Cyclic Allylic Ethers. An Enantioselective Route to Unsaturated Medium Ring Systems

  摘要：

  DOI：

  10.1021/ja960263m

文献信息

• Divergent Enantioselective Synthesis of (−)-Galanthamine and (−)-Morphine
  作者：Barry M. Trost、Weiping Tang、F. Dean Toste

  DOI：10.1021/ja054449+

  日期：2005.10.1

  tricyclic intermediate is available in six steps from 2-bromovanillin and the monoester of methyl 6-hydroxycyclohexene-1-carboxylate. This intermediate requires only two steps to convert to (-)-galanthamine. Using a Heck vinylation, we found that the fourth ring of codeine/morphine could be formed. The final ring formation involves a novel visible light-promoted hydroamination. Thus, six steps are required

  通过采用 Pd 催化的不对称烯丙基烷基化 (AAA) 来设置立体化学，出现了一种用于合成阿片类和石蒜科生物碱的有效发散合成策略。详细讨论了三代加兰他敏的合成，特别关注钯催化的 AAA 反应和分子内 Heck 反应的范围。关键的三环中间体可从 2-溴香草醛和 6-羟基环己烯-1-羧酸甲酯的单酯通过六个步骤获得。该中间体只需两个步骤即可转化为 (-)-雪花胺。使用 Heck 乙烯基化，我们发现可以形成可待因/吗啡的第四个环。最后的环形成涉及一种新型的可见光促进加氢胺化。因此，
• Rapid and Stereoselective C-C, C-O, C-N and C-S Couplings via Microwave Accelerated Palladium-Catalyzed Allylic Substitutions
  作者：Ulf Bremberg、Serghey Lutsenko、Nils-Fredrik Kaiser、Mats Larhed、Anders Hallberg、Christina Moberg

  DOI：10.1055/s-2000-6298

  日期：——

  Palladium-catalyzed substitution of cyclohex-2-en-1-yl ethyl carbonate with neutral C-, O-, and N-nucleophiles was achieved in 1 - 2 minutes using microwave flash heating. Enantioselectivities up to 96% were observed. Ionic nucleophiles tended to result in lower ee. With S-nucleophiles problems with the stability of the nucleophile were encountered.

  使用微波闪热技术，在1到2分钟内实现了钯催化的环己-2-烯-1-基乙基碳酸酯与中性C-、O-和N-亲核试剂的取代反应。观察到高达96%的对映选择性。离子型亲核试剂往往导致较低的对映体过量。对于S-亲核试剂，遇到了亲核试剂稳定性问题。
• Allylation of <i>C</i>‐, <i>N</i>‐, and <i>O</i>‐Nucleophiles via a Mechanochemically‐Driven Tsuji–Trost Reaction Suitable for Late‐Stage Modification of Bioactive Molecules
  作者：Johanna Templ、Michael Schnürch

  DOI：10.1002/anie.202314637

  日期：2024.1.2

  We present the first solvent‐free, mechanochemical protocol for a palladium‐catalyzed Tsuji–Trost allylation. This approach features exceptionally low catalyst loadings (0.5 mol %), short reaction times (<90 min), and a simple setup, eliminating the need for air or moisture precautions, making the process highly efficient and environmentally benign. We introduce solid, nontoxic, and easy‐to‐handle allyl trimethylammonium salts as valuable alternative to volatile or hazardous reagents. Our approach enables the allylation of various O‐, N‐, and C‐nucleophiles in yields up to 99 % even for structurally complex bioactive compounds, owing to its mild conditions and exceptional functional group tolerance.

  摘要 我们首次提出了钯催化辻-特罗斯特烯丙基化反应的无溶剂机械化学方案。这种方法的特点是催化剂负载量极低（0.5 摩尔%）、反应时间短（90 分钟）、设置简单，无需空气或湿气防范措施，因此该工艺高效且对环境无害。我们引入了固体、无毒且易于处理的烯丙基三甲基铵盐，作为挥发性或有害试剂的重要替代品。由于烯丙基三甲基铵的条件温和，对官能团的耐受性极强，即使是结构复杂的生物活性化合物，我们的方法也能使各种 O-、N- 和 C-亲核物的烯丙基化率高达 99%。
• Asymmetric π-allylic etherification of cycloalkenyl esters with phenols in water using a resin-supported chiral palladium complex
  作者：Yasuhiro Uozumi、Masahiro Kimura

  DOI：10.1016/j.tetasy.2005.11.026

  日期：2006.1

  Catalytic asymmetric etherification of cycloalkenyl esters with phenolic nucleophiles was achieved in water as the sole reaction medium under heterogeneous conditions by using 2 mol % palladium of a PS-PEG resin-supported palladium-imidazo-indolephosphine complex to give optically active aryi(cycloalkenyl) ethers with up to 94% ee. (c) 2005 Elsevier Ltd. All rights reserved.
• Asymmetric O- and C-Alkylation of Phenols
  作者：Barry M. Trost、F. Dean Toste

  DOI：10.1021/ja972453i

  日期：1998.2.1