异丙基(2SR,3RS)-2-甲基-3-羟基-3-苯基丙酸酯 | 102285-74-5

• 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: 异丙基(2SR,3RS)-2-甲基-3-羟基-3-苯基丙酸酯
• 英文名称: anti-Isopropyl 3-hydroxy-2-methyl-3-phenylpropionate
• 英文别名: isopropyl anti-3-hydroxy-2-methyl-3-phenylpropanoate；isopropyl (2SR,3RS)-2-methyl-3-hydroxy-3-phenylpropionate；propan-2-yl (2S,3R)-3-hydroxy-2-methyl-3-phenylpropanoate
• CAS: 102285-74-5
• 化学式: C₁₃H₁₈O₃
• 分子量: 222.284
• InChiKey: XNRYDPCVQNKXBY-CMPLNLGQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 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：

  [(2S,3S)-2-甲基-3-苯基-环氧乙烷-2-基]甲醇 在 pyridine-SO3 complex 、 3-benzyl-4,5-dimethylthiazol-3-ium chloride 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 17.0h， 生成 异丙基(2SR,3RS)-2-甲基-3-羟基-3-苯基丙酸酯
  参考文献：
  名称：

  活化羧酸盐的催化生成：从环氧醛直接立体选择性合成 β-羟基酯

  摘要：

  从环氧醛催化生成活化的羧酸盐能够在温和、方便的反应条件下直接、立体选择性地合成 β-羟基酯。除了提供合成抗羟醛加合物的新方法外，这种化学反应还为酯类的催化、无废物合成提供了一种机械可行的解决方案。

  DOI：

  10.1021/ja047407e

文献信息

• Lewis Base Activation of Lewis Acids:  Catalytic, Enantioselective Addition of Silyl Ketene Acetals to Aldehydes
  作者：Scott E. Denmark、Gregory L. Beutner、Thomas Wynn、Martin D. Eastgate

  DOI：10.1021/ja047339w

  日期：2005.3.1

  The concept of Lewis base activation of Lewis acids has been reduced to practice for catalysis of the aldol reaction of silyl ketene acetals and silyl dienol ethers with aldehydes. The weakly acidic species, silicon tetrachloride (SiCl4), can be activated by binding of a strongly Lewis basic chiral phosphoramide, leading to in situ formation of a chiral Lewis acid. This species has proven to be a competent

  路易斯酸的路易斯碱活化的概念已被简化用于催化甲硅烷基乙烯酮缩醛和甲硅烷基二烯醇醚与醛的羟醛反应。弱酸性物质四氯化硅 (SiCl4) 可以通过结合强路易斯碱性手性磷酰胺而被激活，导致手性路易斯酸的原位形成。该物质已被证明是将乙酸酯、丙酸酯和异丁酸酯衍生的甲硅烷基乙烯酮缩醛与共轭和非共轭醛进行羟醛加成反应的有效催化剂。此外，还证明了甲硅烷基二烯醇醚的乙烯基羟醛反应。高水平的区域-，抗非对映-，
• Acyclic stereoselection. 36. Simple diastereoselection in the Lewis acid mediated reactions of enol silanes with aldehydes
  作者：Clayton H. Heathcock、Steven K. Davidsen、Kathleen T. Hug、Lee A. Flippin

  DOI：10.1021/jo00365a033

  日期：1986.7
• Enolboration. 6. Dicyclohexyliodoborane, a Versatile Reagent for the Stereoselective Synthesis of Either Z or E Enolates from Representative Esters
  作者：Kumaraperumal Ganesan、Herbert C. Brown

  DOI：10.1021/jo00088a012

  日期：1994.5

  A smooth, rapid, quantitative, and highly stereoselective synthesis of either Z or E enolates from representative esters has been achieved with dicyclohexyliodoborane, Chx(2)BI, in the presence of a suitable tertiary amine, such as triethylamine or N,N-diisopropylethylamine. A systematic investigation of the enolboration of ethyl propionate and ethyl phenylacetate, as model esters, by the various Chx(2)BX and BX-9-BBN reagents (X = OMs, I, and Br) established Chx(2)BI as the preferred reagent in terms of yield and selectivity. Further study of representative esters (RCH(2)-COOR') with Chx(2)BI established that the steric requirements of both the alkyl group (R) at the ct-position and the alkoxy group (OR') play a significant role in controlling the enolate geometry. The steric requirements of the amine (R''N-3) also contribute considerably to the stereoselectivity of the reaction, The present study provides a simple procedure for the synthesis of Z or E enol borinates from representative esters (RCH(2)COOR') using the combined stereodirecting effects of the alkyl (R) and the alkoxy (OR') groups. These enol borinates are highly reactive with aldehydes at temperatures as low as -78 degrees C and are exceptionally stereoselective even at 0 degrees C, In this exploratory study, the synthesis of stereoselective enolates from representative esters (RCH(2)COOR') using Chx(2)BI/R''N-3 is discussed, with special emphasis on the effects of the steric requirements of R and OR' in controlling the enolate geometry.
• Lanthanoid(II) or -(III) alkoxide-promoted reactions of silyl-ketene acetals with aldehydes
  作者：Yoshikazu Makioka、Ikuko Nakagawa、Yuki Taniguchi、Ken Takaki、Yuzo Fujiwara

  DOI：10.1021/jo00069a055

  日期：1993.8