Tert-butyl 2-oxo-2-(4-phenylphenyl)acetate | 1279017-80-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Tert-butyl 2-oxo-2-(4-phenylphenyl)acetate
• CAS: 1279017-80-9
• 化学式: C₁₈H₁₈O₃
• 分子量: 282.339
• InChiKey: YVWDPXJKDPYUBV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Tert-butyl 2-oxo-2-(4-phenylphenyl)acetate 、 3,4-二氯-2(5H)-呋喃酮 在 (S)-1-(3,5-bis(trifluoromethyl)phenyl)-3-(1-(diethylamino)-3-(1H-indol-3-yl)propan-2-yl)thiourea 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 24.0h， 以92%的产率得到(S)-tert-butyl 2-(4-phenyl-phenyl)-2-((S)-3,4-dichloro-2,5-dihydro-5-oxofuran-2-yl)-2-hydroxyacetate
  参考文献：
  名称：

  呋喃酮与α-酮酸酯的直接不对称葡萄酒醛缩醛反应：获得手性γ-丁烯内酯和甘油衍生物

  摘要：

  两次一样好：使用色氨酸衍生的双官能有机催化剂1进行了标题反应。报道的方法导致以高收率，高非对映选择性和对映选择性选择性合成手性γ-取代的丁烯内酯。还已经证明了容易合成含有叔羟基的手性甘油衍生物。

  DOI：

  10.1002/anie.201006316
• 作为产物：
  描述：

  2-([1,1'-biphenyl]-4-yl)acrylic acid 在 4-二甲氨基吡啶 、 potassium permanganate 、 C₉₄H₁₂₀F₄N₆⁽²⁺⁾*2Cl^(1-) 、 水 、 三乙胺 、 potassium iodide 作用下， 以 二氯甲烷 、 甲基叔丁基醚 为溶剂， 生成 Tert-butyl 2-oxo-2-(4-phenylphenyl)acetate 、 tert-butyl (R)-2-([1,1'-biphenyl]-4-yl)-2,3-dihydroxypropanoate
  参考文献：
  名称：

  Enantioselective Oxidation of Alkenes with Potassium Permanganate Catalyzed by Chiral Dicationic Bisguanidinium

  摘要：

  Chiral anion-controlled ion-pairing catalysis was demonstrated to be a wide-ranging strategy that can utilize a variety of cationic metal species. In a similar manner, we envision a complementary strategy using chiral cation in partnership with inorganic anionic metal salts. Herein, we report a chiral dicationic bisguanidinium-catalyzed asymmetric oxidation reaction of alkenes with potassium permanganate. Chiral induction is attributed to ion-pairing interaction between chiral cation and enolate anion. The success of the current permanganate oxidation reaction together with mechanistic insights should provide inspiration for expansion to other anionic metal salts and would open up new paradigms for asymmetric transition metal catalysis, phase-transfer catalysis, and ion-pairing catalysis.

  DOI：

  10.1021/jacs.5b05792

文献信息

• Preparation of Asymmetric Phase-transfer Catalyst, 1,4-Bis((4S,5S)-1,3-bis(3,5-di-tert-butylbenzyl)-4,5-diphenylimidazolidin-2-ylidene)piperazine-1,4-diium chloride
  作者：Esther Cai Xia Ang

  DOI：10.15227/orgsyn.097.0274

  日期：——
• US7534894B2
  申请人：——

  公开号：US7534894B2

  公开（公告）日：2009-05-19
• Enantioselective Oxidation of Alkenes with Potassium Permanganate Catalyzed by Chiral Dicationic Bisguanidinium
  作者：Chao Wang、Lili Zong、Choon-Hong Tan

  DOI：10.1021/jacs.5b05792

  日期：2015.8.26

  Chiral anion-controlled ion-pairing catalysis was demonstrated to be a wide-ranging strategy that can utilize a variety of cationic metal species. In a similar manner, we envision a complementary strategy using chiral cation in partnership with inorganic anionic metal salts. Herein, we report a chiral dicationic bisguanidinium-catalyzed asymmetric oxidation reaction of alkenes with potassium permanganate. Chiral induction is attributed to ion-pairing interaction between chiral cation and enolate anion. The success of the current permanganate oxidation reaction together with mechanistic insights should provide inspiration for expansion to other anionic metal salts and would open up new paradigms for asymmetric transition metal catalysis, phase-transfer catalysis, and ion-pairing catalysis.
• The Direct Asymmetric Vinylogous Aldol Reaction of Furanones with α-Ketoesters: Access to Chiral γ-Butenolides and Glycerol Derivatives
  作者：Jie Luo、Haifei Wang、Xiao Han、Li-Wen Xu、Jacek Kwiatkowski、Kuo-Wei Huang、Yixin Lu

  DOI：10.1002/anie.201006316

  日期：2011.2.18

  Twice as good: The title reaction using the tryptophan‐derived bifunctional organic catalyst 1 has been developed. The reported method led to the synthesis of chiral γ‐substituted butenolides in excellent yields, with high diastereo‐ and enantioselectivities. Facile synthesis of chiral glycerol derivatives containing a tertiary hydroxy group has also been demonstrated.

  两次一样好：使用色氨酸衍生的双官能有机催化剂1进行了标题反应。报道的方法导致以高收率，高非对映选择性和对映选择性选择性合成手性γ-取代的丁烯内酯。还已经证明了容易合成含有叔羟基的手性甘油衍生物。