ethyl 2-methylmandelate | 421545-88-2

• 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: ethyl 2-methylmandelate
• 英文别名: (R)-ethyl-2-methylmandelate；Ethyl (I+/-R)-I+/--hydroxy-2-methylbenzeneacetate；ethyl (2R)-2-hydroxy-2-(2-methylphenyl)acetate
• CAS: 421545-88-2
• 化学式: C₁₁H₁₄O₃
• 分子量: 194.23
• InChiKey: AVEHFDPFEUTTSP-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  乙基(2-甲基苯基)(氧代)乙酸酯 在 bis(1,5-cyclooctadiene)diiridium(I) dichloride 、 potassium tert-butylate 、 C₃₇H₃₅FeN₂P 作用下， 以 乙醇 为溶剂， 20.0 ℃ 、2.03 MPa 条件下， 生成 ethyl 2-methylmandelate 、 ethyl 2-methylmandelate
  参考文献：
  名称：

  铱催化不对称氢化α-羰基酸酯制手性α-羟基酸酯的方法

  摘要：

  本发明提供一种铱催化不对称氢化α‑羰基酸酯制备手性α‑羟基酸酯的方法，该手性α‑羟基酸酯化合物的制备方法为：在充满氮气的手套箱内，将环辛二烯氯化铱二聚体([Ir(COD)Cl]

  公开号：

  CN116135834A

文献信息

• Dynamic Kinetic Resolution via Dual-Function Catalysis of Modified Cinchona Alkaloids:  Asymmetric Synthesis of α-Hydroxy Carboxylic Acids
  作者：Liang Tang、Li Deng

  DOI：10.1021/ja0255047

  日期：2002.3.1

  dioxolanediones was realized via a modified cinchona alkaloid-catalyzed alcoholytic opening of the dioxolanedione ring, generating a variety of optically active alpha-hydroxy esters in 91-96% ee and 61-85% chemical yield. In this dynamic kinetic resolution, the modified cinchona alkaloid was found to serve dual catalytic roles, mediating both the rapid racemization of the 5-aryl dioxolanediones and the enantioselective

  报道了外消旋 α-羟基酸向光学活性 α-羟基酸的高度对映选择性催化转化。开发了一种新方法，用于在室温下，在活性炭存在下，外消旋 α-羟基酸与氯甲酸三氯甲酯（双光气）缩合形成 90-100 中的 5-取代-1,3-二氧戊环-2,4-二酮％ 屈服。通过改性金鸡纳生物碱催化的二氧戊环醇解开环实现了 5-芳基二氧戊环二酮的有效动态动力学拆分，以 91-96% ee 和 61-85% 化学产率生成各种光学活性 α-羟基酯。在这种动态动力学解析中，发现改性金鸡纳生物碱具有双重催化作用，介导 5-芳基二氧戊环二酮的快速外消旋化和 5-芳基二氧戊环二酮的对映选择性醇解开环。因此，5-芳基二氧戊环二酮的两种对映异构体均以产率 (61-85%) 转化为高度对映异构的芳香族 α-羟基酯，远远超过正常动力学分辨率的最大值 50%。这一发展不仅代表了合成催化剂不对称酰基转移催化范围的扩展，而且为开发由单一催化剂促进
• Ru-Catalyzed Asymmetric Hydrogenation of α-Ketoesters with CeCl₃·7H₂O as Additive
  作者：Yanhui Sun、Xiaobing Wan、Jianping Wang、Qinghua Meng、Hongwei Zhang、Lijuan Jiang、Zhaoguo Zhang

  DOI：10.1021/ol052212c

  日期：2005.11.1

  An efficient asymmetric hydrogenation of alpha-ketoesters is reported with use of a catalyst prepared from [Ru((S)-3)(benzene)Cl]Cl and CeCl3-7H(2)O. a-Hydroxy esters are obtained in up to 96% ee. The addition of CeCl3-7H(2)O not only improves the enantioselectivity, but also enhances the stability of the catalyst. As a result, the hydrogenation of methyl benzoylformate affords the product with 92% ee with a substrate/catalyst ratio of 10 000. Hydrolysis of 2 provides the final compound with 83% yield at 99% ee after a single recrystallization from 1,2-dichloroethylene.
• CeCl₃·7H₂O: An Effective Additive in Ru-Catalyzed Enantioselective Hydrogenation of Aromatic α-Ketoesters
  作者：Qinghua Meng、Yanhui Sun、Virginie Ratovelomanana-Vidal、Jean Pierre Genêt、Zhaoguo Zhang

  DOI：10.1021/jo800228e

  日期：2008.5.1

  In the presence of catalytic amounts of CeCl3 center dot 7H(2)O, [RuCl(benzene)(S)-SunPhos]Cl is a highly effective catalyst for the asymmetric hydrogenation of aromatic alpha-ketoesters. A variety of ethyl alpha-hydroxy-alpha-arylacetates have been prepared in up to 98.3% ee with a TON up to 10 000. Challenging aromatic alpha-ketoesters with ortho substituents are also hydrogenated with high enantioselectivities. The addition of CeCl3 center dot 7H(2)O not only improves the enantioselectivity but also enhances the stability of the catalyst. The ratio of CeCl3 center dot 7H(2)O to [RuCl(benzene)(S)-SunPhos]Cl plays an important role in the hydrogenation reaction with a large substrate/catalyst ratio.