2-羟基-2-甲基-3-苯基丙酸乙酯 | 223480-34-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-羟基-2-甲基-3-苯基丙酸乙酯
• 英文名称: ethyl 2-hydroxy-2-methyl-3-phenylpropanoate
• CAS: 223480-34-0
• 化学式: C₁₂H₁₆O₃
• 分子量: 208.257
• InChiKey: FQFYVYZSUGJWPZ-UHFFFAOYSA-N

物化性质

• 沸点：
  141-142 °C(Press: 19 Torr)
• 密度：
  1.100±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 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：

  2-羟基-2-甲基-3-苯基丙酸乙酯 在 碘苯二乙酸 、 palladium diacetate 、 lithium carbonate 作用下， 以 六氟苯 为溶剂， 反应 36.0h， 以50%的产率得到ethyl 2-methyl-2,3-dihydrobenzofuran-2-carboxylate
  参考文献：
  名称：

  Pd(II)-Catalyzed Hydroxyl-Directed C−H Activation/C−O Cyclization: Expedient Construction of Dihydrobenzofurans

  摘要：

  A Pd(II)-catalyzed C-H activation/C-O cyclization reaction directed by a proximate hydroxyl group has been developed. This reaction provides a new method for constructing dihydrobenzofurans, including spirocyclic analogues, a process that is potentially applicable to natural product synthesis.

  DOI：

  10.1021/ja105366u
• 作为产物：
  描述：

  (R,S)-2-hydroxy-2-methyl-3-phenylpropanoic acid 生成 2-羟基-2-甲基-3-苯基丙酸乙酯
  参考文献：
  名称：

  Davies et al., Journal of the Chemical Society, 1950, p. 34

  摘要：

  DOI：

文献信息

• Mitsunobu Approach to the Synthesis of Optically Active α,α-Disubstituted Amino Acids
  作者：Jonathan E. Green、David M. Bender、Stona Jackson、Martin J. O’Donnell、James R. McCarthy

  DOI：10.1021/ol802325h

  日期：2009.2.19

  α-azido esters by Mitsunobu reaction with HN3. Optimization of this reaction was shown to proceed at room temperature with high chemical yield using 1,1-(azodicarbonyl)dipiperidine (ADDP) and trimethylphosphine (PMe3). Complete inversion of configuration was observed at the α-carbon. Several α,α-disubstituted amino acids were synthesized in high overall chemical yield and optical purity.

  已知立体化学构型的手性叔α-羟基酯通过与​​HN 3的Mitsunobu反应转化为α-叠氮基酯。已表明，使用1,1-（偶氮二羰基）二哌啶（ADDP）和三甲基膦（PMe 3）可以在室温下以高化学收率进行该反应的优化。在α-碳处观察到构型完全反转。以高的总化学产率和光学纯度合成了几种α，α-二取代的氨基酸。
• Preparation of<i>tert</i>-Alkyl Aryl Sulfides from<i>tert</i>-Alcohols via Quinone-mediated Oxidation–Reduction Condensation between<i>tert</i>-Alkyl Diphenylphosphinites and 2-Sulfanyl-1,3-benzothiazole
  作者：Kazuhiro Ikegai、Wanchai Pluempanupat、Teruaki Mukaiyama

  DOI：10.1246/cl.2005.638

  日期：2005.5

  A convenient two-step procedure for the construction of sulfur-containing quaternary centers from tert-alcohols involving chiral ones is established. tert-Alkyl diphenylphosphinites 1 were easily prepared in excellent yields from tert-alcohols and ClPPh2 by the combined use of Et3N and a catalytic amount of DMAP. Subsequent condensation of 1 with thiol 3 smoothly proceeded in the presence of quinone 2d to afford the corresponding tert-alkyl sulfides 4 in good to high yields via SN2 displacement. Removal of benzothiazol-2-yl group of (R)-4j was achieved with LiAlH4 to afford the desired chiral thiol (R)-5 in high yield.

  建立了一种从涉及手性叔醇的叔醇出发，构建含硫季碳中心的方便两步法。叔烷基二苯膦亚基1可通过叔醇与ClPPh2在Et3N和催化量DMAP的共同作用下，轻松制备并获得极佳产率。随后，在醌2d的存在下，1与硫醇3的缩合反应顺利进行，通过SN2取代反应以良好至高产率得到相应的叔烷基硫醚4。使用LiAlH4去除(R)-4j的苯并噻唑-2-基团，以高产率得到了所需的手性硫醇(R)-5。
• Manganese(IV)‐Mediated Hydroperoxyarylation of Alkenes with Aryl Hydrazines and Dioxygen from Air
  作者：Stephanie Kindt、Hannelore Jasch、Markus R. Heinrich

  DOI：10.1002/chem.201400064

  日期：2014.5.19

  version of the Meerwein arylation in which the introduction of oxygen is achieved by using dioxygen from the air. In this way, hydroperoxides were obtained from activated as well as non‐activated alkenes by oxidizing aryl hydrazines with manganese dioxide. The best results were obtained with α‐substituted acrylates. Importantly, the aryl hydrazine has to be added slowly to the reaction mixture to allow

  我们报告了Meerwein芳基化的新的碳氧加合类型，其中氧气的引入是通过使用空气中的双氧来实现的。通过这种方式，通过用二氧化锰氧化芳基肼，从活化的和未活化的烯烃中获得了氢过氧化物。用α-取代的丙烯酸酯可获得最佳结果。重要的是，必须将芳基肼缓慢加入反应混合物中，以使空气中的双氧充分吸收。竞争和标记实验表明氢过氧自由基是新型的以氧为中心的自由基清除剂。
• [EN] SPIRO-OXAZOLONES<br/>[FR] SPIRO-OXAZOLONES
  申请人：HOFFMANN LA ROCHE

  公开号：WO2015124541A1

  公开（公告）日：2015-08-27

  The present invention provides spiro-oxazolones, which act as V1a receptor modulators, and in particular as V1a receptor antagonists, their manufacture, pharmaceutical compositions containing them and their use as medicaments. The present compounds are useful as therapeutics acting peripherally and centrally in the conditions of inappropriate secretion of vasopressin, anxiety, depressive disorders, obsessive compulsive disorder, autistic spectrum disorders, schizophrenia, aggressive behavior and phase shift sleep disorders, in particular jetlag.

  本发明提供了螺环噁唑酮，其作为V1a受体调节剂，特别是作为V1a受体拮抗剂，其制备方法，含有它们的药物组合物以及它们作为药物的用途。本化合物在周围和中枢作用下，对于不当分泌加压素、焦虑、抑郁症、强迫症、自闭症谱系障碍、精神分裂症、攻击性行为和相位错位性睡眠障碍，特别是时差反应等症状的治疗具有用处。
• Copper(II)-catalyzed O-Phenylation of Tertiary Alcohols with Organobismuth(V) Reagents
  作者：Kazuhiro Ikegai、Kentarou Fukumoto、Teruaki Mukaiyama

  DOI：10.1246/cl.2006.612

  日期：2006.6

  A new method for the Cu(OAc)2-catalyzed phenylation of tertiary alcohols under mild basic conditions is described. Triphenylbismuth(V) diacetate and tetraphenylbismuth reagents undergo cross-coupli...

  描述了一种在温和碱性条件下对叔醇进行 Cu(OAc)2 催化苯基化的新方法。三苯基铋(V)二乙酸酯和四苯基铋试剂发生交叉偶联...