[(3R)-4,4-dimethyl-2-oxooxolan-3-yl] (E,2S)-2-hydroxy-4-phenylbut-3-enoate | 161260-69-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醇
• 英文名称: [(3R)-4,4-dimethyl-2-oxooxolan-3-yl] (E,2S)-2-hydroxy-4-phenylbut-3-enoate
• CAS: 161260-69-1
• 化学式: C₁₆H₁₈O₅
• 分子量: 290.316
• InChiKey: LDNOWOGRFGJDNK-TYDXBBDOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [(3R)-4,4-dimethyl-2-oxooxolan-3-yl] (E,2S)-2-hydroxy-4-phenylbut-3-enoate 在 palladium on activated charcoal 过氧化氢,锂盐(1:1) 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 为溶剂， 反应 4.0h， 生成 (S)-(+)-methyl-2-hydroxy-4-phenylbutanoate
  参考文献：
  名称：

  A Stereospecific Access to Allylic Systems Using Rhodium(II)−Vinyl Carbenoid Insertion into Si−H, O−H, and N−H Bonds

  摘要：

  Rhodium-catalyzed decomposition of alpha-vinyldiazoesters in the presence of silanes, alcohols, ethers, amines, and thiols have been shown to produce the corresponding alpha-silyl, alpha-hydroxy, alpha-alkoxy, alpha-amino, and alpha-thioalkoxy esters in generally good yield with a complete retention of the stereochemistry of the double bond of the diazo precursor. An extension of the process in homochiral series has also been devised using either a chiral auxiliary attached to the ester function or achiral alpha-vinyldiazoesters and Doyle's chiral catalyst Rh-2(MEPY)(4). In the former approach, pantolactone as chiral auxiliary gave diastereoselectivities of up to 70%, while the second approach produced the desired allylsilane with ee as high as 72%. On the other hand, Rh-2(MEPY)(4)-catalyzed insertion into the O-H bond of water led to poor or no enantioselectivity in good agreement with recent literature reports.

  DOI：

  10.1021/jo961952j
• 作为产物：
  描述：

  (3R)-3-(4,4-dimethyl-2-oxotetrahydrofuranyl) (E)-2-diazo-4-phenyl-3-butenoate 在 Rh₂(4R-MEAZ)4 、 水 作用下， 以 二氯甲烷 为溶剂， 生成 (E)-(R)-2-Hydroxy-4-phenyl-but-3-enoic acid (R)-4,4-dimethyl-2-oxo-tetrahydro-furan-3-yl ester 、 [(3R)-4,4-dimethyl-2-oxooxolan-3-yl] (E,2S)-2-hydroxy-4-phenylbut-3-enoate
  参考文献：
  名称：

  手性催化剂增强非对映异构控制泛内酯的苯乙烯基和苯基重氮乙酸酯的OH插入反应

  摘要：

  手性dirhodium（II）催化剂Rh 2（MEAZ）4与Rh 2（OAc）4相比，提高了对具有手性助剂的重氮酯的分子间O insertionH插入反应的非对映控制。

  DOI：

  10.1016/s0040-4039(02)01282-0

文献信息

• Rhodium(II)-vinylcarbenoid insertion into the SiH bond. A new stereospecific synthesis of allylsilanes
  作者：Yannick Landais、Denis Planchenault、Valéry Weber

  DOI：10.1016/0040-4039(94)88508-7

  日期：1994.12

  catalysed decomposition of vinyldiazocarbonyl compounds in the presence of organosilanes led stereospecifically to the corresponding allylsilanes in good yields. An asymmetric approach has also been considered as well as the extension of the methodology to the synthesis of other allylic systems.

  在有机硅烷的存在下，Rh 2（OAc）4催化的乙烯基重氮羰基化合物的分解立体定向地以良好的收率生成了相应的烯丙基硅烷。还考虑了不对称方法，以及将方法扩展到其他烯丙基系统的合成。
• A Stereospecific Access to Allylic Systems Using Rhodium(II)−Vinyl Carbenoid Insertion into Si−H, O−H, and N−H Bonds
  作者：Priyadarshanie Bulugahapitiya、Yannick Landais、Liliana Parra-Rapado、Denis Planchenault、Valéry Weber

  DOI：10.1021/jo961952j

  日期：1997.3.1

  Rhodium-catalyzed decomposition of alpha-vinyldiazoesters in the presence of silanes, alcohols, ethers, amines, and thiols have been shown to produce the corresponding alpha-silyl, alpha-hydroxy, alpha-alkoxy, alpha-amino, and alpha-thioalkoxy esters in generally good yield with a complete retention of the stereochemistry of the double bond of the diazo precursor. An extension of the process in homochiral series has also been devised using either a chiral auxiliary attached to the ester function or achiral alpha-vinyldiazoesters and Doyle's chiral catalyst Rh-2(MEPY)(4). In the former approach, pantolactone as chiral auxiliary gave diastereoselectivities of up to 70%, while the second approach produced the desired allylsilane with ee as high as 72%. On the other hand, Rh-2(MEPY)(4)-catalyzed insertion into the O-H bond of water led to poor or no enantioselectivity in good agreement with recent literature reports.
• Chiral catalyst enhancement of diastereocontrol for OH insertion reactions of styryl- and phenyldiazoacetate esters of pantolactone
  作者：Michael P. Doyle、Ming Yan

  DOI：10.1016/s0040-4039(02)01282-0

  日期：2002.8

  The chiral dirhodium(II) catalyst Rh2(MEAZ)4 increases diastereocontrol for intermolecular OH insertion reactions of diazo esters having a chiral auxiliary over that achieved with Rh2(OAc)4.

  手性dirhodium（II）催化剂Rh 2（MEAZ）4与Rh 2（OAc）4相比，提高了对具有手性助剂的重氮酯的分子间O insertionH插入反应的非对映控制。