2-hydroxyethyl (Z)-3-(4-hydroxy-3-methoxyphenyl)-acetylaminopropenoate | 149150-92-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-hydroxyethyl (Z)-3-(4-hydroxy-3-methoxyphenyl)-acetylaminopropenoate
• 英文别名: 2-hydroxyethyl (Z)-2-acetamido-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
• CAS: 149150-92-5
• 化学式: C₁₄H₁₇NO₆
• 分子量: 295.292
• InChiKey: PHNYFDRZNJEYJV-XFFZJAGNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  105
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-hydroxyethyl (Z)-3-(4-hydroxy-3-methoxyphenyl)-acetylaminopropenoate 在 BF4 氢气 作用下， 以 甲醇 为溶剂， 25.0 ℃ 、100.0 kPa 条件下， 反应 2.0h， 以0.75 g的产率得到(S)-2-hydroxyethyl N-acetyl-4-hydroxy-3-methoxyphenylalaninate
  参考文献：
  名称：

  Application of the term “relative enantioselectivity” as useful measure for comparison of chiral catalysts, demonstrated on asymmetric hydrogenation of amino acid precursors

  摘要：

  The application of the quotient ''relative enantioselectivity'' Q = q/q' in which q and q' are enantiomenc ratios R/S (or S/R) for two comparable cases of asymmetric synthesis experiments is recommended for comparison of two or more catalysts or other variables like solvents, substrates and cofactors. The importance of this term Q lies in the possibility to form and compare values of enantioselectivity over the whole range from 99,9 % ee (R) to 99,9 % ee (S) in a mathematically correct way and is demonstrated on multiple examples of asymmetric hydrogenation of partly new N-acyl-dehydroamino acid derivatives with a couple of catalysts [Rh(Ph-beta-glup)(COD)]BF4 1 and [Rh(Ph-beta-glup-OH)(COD)]BF4 2. Interesting inversions of Q could be discovered for changes of the type of substrate and in dependence of the polarity of solvents.

  DOI：

  10.1016/s0957-4166(00)86082-6
• 作为产物：
  描述：

  乙二醇 、 methyl (Z)-3-(4-acetoxy-3-methoxyphenyl)-2-acetylaminopropenoate 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 6.0h， 以50%的产率得到2-hydroxyethyl (Z)-3-(4-hydroxy-3-methoxyphenyl)-acetylaminopropenoate
  参考文献：
  名称：

  Application of the term “relative enantioselectivity” as useful measure for comparison of chiral catalysts, demonstrated on asymmetric hydrogenation of amino acid precursors

  摘要：

  The application of the quotient ''relative enantioselectivity'' Q = q/q' in which q and q' are enantiomenc ratios R/S (or S/R) for two comparable cases of asymmetric synthesis experiments is recommended for comparison of two or more catalysts or other variables like solvents, substrates and cofactors. The importance of this term Q lies in the possibility to form and compare values of enantioselectivity over the whole range from 99,9 % ee (R) to 99,9 % ee (S) in a mathematically correct way and is demonstrated on multiple examples of asymmetric hydrogenation of partly new N-acyl-dehydroamino acid derivatives with a couple of catalysts [Rh(Ph-beta-glup)(COD)]BF4 1 and [Rh(Ph-beta-glup-OH)(COD)]BF4 2. Interesting inversions of Q could be discovered for changes of the type of substrate and in dependence of the polarity of solvents.

  DOI：

  10.1016/s0957-4166(00)86082-6

文献信息

• Asymmetric hydrogenation - influence of the structure of carbohydrate derived catalysts on the relative enantioselectivity QH/Me regarding acid and ester substrates and its inversion - selectivity increase in water by amphiphiles
  作者：Rüdiger Selke、Manuela Ohff、Andreas Riepe

  DOI：10.1016/s0040-4020(96)00953-2

  日期：1996.11

  resulting in an unusual low relative enantioselectivityQ=qH/qMe of 0.3 for the precatalysts 4e and 4f. Deprotected, 4,6-OH-group bearing catalysts 1-4g,h generally show smaller differences of %ee in methanol or benzene, however, not in water. Under addition of amphiphiles a in comparison with blanks b the relative enantioselectivity Q=qa/qb clearly increases for both groups of catalysts - in most cases

  4,6 - O-苄叉基保护的2,3-双（O-二苯基膦基）-δ-吡喃葡萄糖苷铑（I）螯合物预催化剂1-4e ，f显示了对（Z）-2- N-酰氨基丙烯酸甲酯的加氢作用6 -8随轴向取向的六吡喃糖苷取代基数量的增加，对映选择性逐步降低。对于类似的底物酸6h-8h的降低甚至更强，导致预催化剂4e和4f的相对低的相对对映选择性Q = q H / q Me为0.3。脱保护的含4,6-OH基的催化剂1-4g，h通常在甲醇或苯中显示出较小的％ee差异，而在水中则显示出较小的％ee差异。与空白b相比，在添加两亲性a的情况下，两组催化剂的相对对映选择性Q = q a / q b明显增加-在大多数情况下，Q值在3到8之间-与催化剂的中性或离子性质无关两亲的。
• Kumar, Arvind; Oehme, Guenther; Roque, Jean Pierre, Angewandte Chemie, 1994, vol. 106, # 21, p. 2272 - 2275
  作者：Kumar, Arvind、Oehme, Guenther、Roque, Jean Pierre、Schwarze, Manuela、Selke, Ruediger

  DOI：——

  日期：——
• Application of the term “relative enantioselectivity” as useful measure for comparison of chiral catalysts, demonstrated on asymmetric hydrogenation of amino acid precursors
  作者：Rüdiger Selke、Christine Facklam、Heinrich Foken、Detlef Heller

  DOI：10.1016/s0957-4166(00)86082-6

  日期：1993.3

  The application of the quotient ''relative enantioselectivity'' Q = q/q' in which q and q' are enantiomenc ratios R/S (or S/R) for two comparable cases of asymmetric synthesis experiments is recommended for comparison of two or more catalysts or other variables like solvents, substrates and cofactors. The importance of this term Q lies in the possibility to form and compare values of enantioselectivity over the whole range from 99,9 % ee (R) to 99,9 % ee (S) in a mathematically correct way and is demonstrated on multiple examples of asymmetric hydrogenation of partly new N-acyl-dehydroamino acid derivatives with a couple of catalysts [Rh(Ph-beta-glup)(COD)]BF4 1 and [Rh(Ph-beta-glup-OH)(COD)]BF4 2. Interesting inversions of Q could be discovered for changes of the type of substrate and in dependence of the polarity of solvents.