3-(2-methoxymethylphenyl)propenoic acid | 135679-45-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 3-(2-methoxymethylphenyl)propenoic acid
• 英文别名: (E)-3-[2-(methoxymethyl)phenyl]prop-2-enoic acid
• CAS: 135679-45-7
• 化学式: C₁₁H₁₂O₃
• 分子量: 192.214
• InChiKey: OQBYLMGIBSGXSC-VOTSOKGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(2-methoxymethylphenyl)propenoic acid 在 硫酸 、 氨 、 氯化铵 作用下， 以 乙醚 为溶剂， 反应 14.0h， 生成 4-<2-methoxymethylphenyl>-2-pentanone
  参考文献：
  名称：

  Stereoselective addition of R2CuLi to ortho-substituted methyl cinnamates intramolecular assistance and solvent effects

  摘要：

  High chemical yields are obtained on the addition of the ortho-substituted enoates 1,2,3, and 4 to Me2CuLi or Ph2CuLi in non-coordinating solvents, CH2Cl2 or toluene. The results underline the strong effect of solvent on reactions between organocuprates and enoates as the corresponding reactions in diethyl ether afforded low yields and moderate steroselectivity. No reaction was observed when THF was used. The high steroselectivity observed with the dimethylaminoethyl substituted enoate 4 in non-coordinating solvents can be accommodated by a mechanistic model for the reaction based on chelation control, within a copper-alkene pi-complex.

  DOI：

  10.1016/s0040-4020(01)86478-4
• 作为产物：
  描述：

  1-溴-2-(甲氧基甲基)苯 在 哌啶 、 正丁基锂 作用下， 以 吡啶 为溶剂， 反应 5.5h， 生成 3-(2-methoxymethylphenyl)propenoic acid
  参考文献：
  名称：

  Stereoselective addition of R2CuLi to ortho-substituted methyl cinnamates intramolecular assistance and solvent effects

  摘要：

  High chemical yields are obtained on the addition of the ortho-substituted enoates 1,2,3, and 4 to Me2CuLi or Ph2CuLi in non-coordinating solvents, CH2Cl2 or toluene. The results underline the strong effect of solvent on reactions between organocuprates and enoates as the corresponding reactions in diethyl ether afforded low yields and moderate steroselectivity. No reaction was observed when THF was used. The high steroselectivity observed with the dimethylaminoethyl substituted enoate 4 in non-coordinating solvents can be accommodated by a mechanistic model for the reaction based on chelation control, within a copper-alkene pi-complex.

  DOI：

  10.1016/s0040-4020(01)86478-4

文献信息

• [EN] TWO STEP SYNTHESIS OF D- AND L- alpha -AMINO ACIDS AND D- AND L- alpha -AMINO ALDEHYDES<br/>[FR] SYNTHESE EN DEUX ETAPES D' alpha AMINO-ACIDES D ET L ET D' alpha AMINO-ALDEHYDES D ET L
  申请人：——

  公开号：WO1997044312A1

  公开（公告）日：1997-11-27

  [EN] D- and L- alpha -amino acids and D- and L- alpha -amino aldehydes are synthesized from olefin substrates in two steps. The first step is a catalyzed asymmetric aminohydroxylation addition reaction to the olefin substrate. The addition reaction is catalyzed by osmium and is co-catalyzed by chiral ligands. The chiral ligands, in addition to being co-catalysts with the osmium, also serve to direct the addition reaction regioselectively and enantioselectively. Divalent ligands are preferred over monovalent ligands because of their enhanced regio- and enantio-selectivity. As an oxidant nitrogen source for the addition reaction, either a carbamate or sulfonamide may be employed. If carbamate is employed as an oxidant nitrogen source, the resultant beta -hydroxycarbamate is deprotected to yield the corresponding beta -hydroxyamine. If sulfonamide is employed as an oxidant nitrogen source, the resultant beta -hydroxysulfonamide is deprotected to yield the corresponding beta -hydroxyamine. The resultant beta -hydroxamine is then selectively oxidized in a second synthetic step to produce the desired D- and L- alpha -amino acid or D- and L- alpha -amino aldehyde.
  [FR] On synthétise des alpha -amino-acides D et L et des alpha -amino-adlhéhydes D et L à partir de substrats oléfines en deux étapes. La première étape est une réaction d'addition d'aminohydroxylation asymétrique catalysée. La réaction d'addition est catalysée par l'osmium et cocatalysée par des ligands chiraux. Les ligands chiraux, outre le fait qu'ils sont cocatalyseurs avec l'osmium, servent à diriger la réaction d'addition de manière régiosélective et énantiosélective. Les ligands bivalents sont préférés aux ligands monovalents en raison de leur régiosélectivité et de leur énantiosélectivité améliorées. Comme source azotée oxydante pour la réaction d'addition, on peut employer un carbamate ou un sulfamide. Dans le cas où on emploie un carbamate comme source azotée oxydante pour la réaction d'addition, l'hydroxycarbamate beta obtenu est déprotégé afin de produire l'hydroxyamine beta correspondante. Dans le cas où on emploie un sulfamide comme source azotée oxydante pour la réaction d'addition, l'hydroxysulfamide beta obtenue est déprotégée afin de produire l'hydroxyamine beta correspondante. L'hydroxyamine beta obtenue est ensuite oxydée de manière sélective dans une deuxième étape afin de produire l' alpha -amino-acide D et L ou l' alpha -amino-adlhéhyde D et L désiré.
• Stereoselective addition of R2CuLi to ortho-substituted methyl cinnamates intramolecular assistance and solvent effects
  作者：Beritte Christenson、Gerd Hallnemo、Christina Ullenius

  DOI：10.1016/s0040-4020(01)86478-4

  日期：1991.1

  High chemical yields are obtained on the addition of the ortho-substituted enoates 1,2,3, and 4 to Me2CuLi or Ph2CuLi in non-coordinating solvents, CH2Cl2 or toluene. The results underline the strong effect of solvent on reactions between organocuprates and enoates as the corresponding reactions in diethyl ether afforded low yields and moderate steroselectivity. No reaction was observed when THF was used. The high steroselectivity observed with the dimethylaminoethyl substituted enoate 4 in non-coordinating solvents can be accommodated by a mechanistic model for the reaction based on chelation control, within a copper-alkene pi-complex.