methyl 2-amino-3-hydroxy-3-(4-methoxyphenyl)propanoate | 118537-22-7

• 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: methyl 2-amino-3-hydroxy-3-(4-methoxyphenyl)propanoate
• 英文别名: (2RS,3RS)-2-amino-3-hydroxy-3-(4-methoxy-phenyl)-propionic acid methyl ester；methyl (2S,3S)-2-amino-3-hydroxy-3-(4-methoxyphenyl)propanoate
• CAS: 118537-22-7
• 化学式: C₁₁H₁₅NO₄
• 分子量: 225.244
• InChiKey: BJYSPCWKFRYEIW-UWVGGRQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  81.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 2-amino-3-hydroxy-3-(4-methoxyphenyl)propanoate 、 苯甲亚胺酸乙酯 生成 cis-Oxazolin (s.F.)
  参考文献：
  名称：

  Substituent effects in the reaction of N-benzoyl-.beta.-arylserinates with thionyl chloride

  摘要：

  DOI：

  10.1021/jo00967a023
• 作为产物：
  描述：

  methyl 2-(dibenzylamino)-3-hydroxy-3-(4-methoxyphenyl)propanoate 在 20 % Pd(OH)2/C 、 氢气 作用下， 以 甲醇 为溶剂， 以97%的产率得到methyl 2-amino-3-hydroxy-3-(4-methoxyphenyl)propanoate
  参考文献：
  名称：

  S_N1-Type Substitution Reactions ofN-Protected β-Hydroxytyrosine Esters: Stereoselective Synthesis of β-Aryl and β-Alkyltyrosines

  摘要：

  AbstractThe title compounds were prepared by aldol reaction of anisaldehyde and the respective N,N‐dibenzyl glycinates. Deprotection of the nitrogen atom with Pearlman’s catalyst delivered the unprotected β‐hydroxytyrosine esters, which were further N‐protected as N,N‐phthaloyl (Phth) and N‐fluorenylmethylcarbonyloxy (Fmoc) derivatives. The Friedel–Crafts reaction with various arenes was studied employing these alcohols as electrophiles. It turned out that the facial diastereoselectivitiy depends on the nitrogen protecting group and on the ester group. The unprotected substrates (NH2) gave preferentially syn‐products but the anti‐selectivity increased when going from NHFmoc over NPhth to NBn2. If the ester substituent was varied the syn‐preference increased in the order Me <Et <iPr. The reactions were shown to be fully stereoconvergent and proceeded under kinetic product control. A model is suggested to explain the facial diastereoselectivity based on a conformationally locked benzylic cation intermediate. The reactions are preparatively useful for the N‐unprotected isopropyl ester, which gave Friedel–Crafts alkylation products with good syn‐selectivity (anti/syn=21:79 to 7:93), and for the N,N‐dibenzyl‐protected methyl ester, which led preferentially to anti‐products (anti/syn=80:20 to >95:5). Upon acetylation of the latter compound to the respective acetate, Bi(OTf)3‐catalyzed alkylation reactions became possible, in which silyl enol ethers served as nucleophiles. The respective alkylation products were obtained in high yield and with excellent anti‐selectivitiy (anti/syn≥95:5).

  DOI：

  10.1002/asia.201101016

文献信息

• Aza-Darzens Asymmetric Synthesis of <i>N</i>-(<i>p</i>-Toluenesulfinyl)aziridine 2-Carboxylate Esters from Sulfinimines (<i>N</i>-Sulfinyl Imines)
  作者：Franklin A. Davis、Hu Liu、Ping Zhou、Tianan Fang、G. Venkat Reddy、Yulian Zhang

  DOI：10.1021/jo990907j

  日期：1999.10.1

  The one-step aza-Darzens reaction of sulfinimines 2 with lithium alpha-bromoenolates readily affords diversely substituted cis and trans N-sulfinylaziridine 2-carboxylate esters 3 and 7 in good yield and excellent diastereoselectivity. Higher yields, but lower de's, result when a mixture of the alpha-bromo ester and 2 are treated with base. The N-sulfinyl group is transformed, nearly quantitatively, without ring opening, into the N-tosyl activating group by oxidation with m-CPBA. Selective removal of the N-sulfinyl group in aziridines 3a and 3h with TFA/H2O affords VI-aziridines 21 which are difficult to prepared by other means. However, C(3) activated azirines such as 3b undergo ring-opening under these conditions. Alternatively, the N-sulfinyl group, even in C(3)-activated aziridines, was selectively and efficiently removed by treatment of the aziridine with 2 equiv of MeMgBr.
• S_N1-Type Substitution Reactions of<i>N</i>-Protected β-Hydroxytyrosine Esters: Stereoselective Synthesis of β-Aryl and β-Alkyltyrosines
  作者：David Wilcke、Eberhardt Herdtweck、Thorsten Bach

  DOI：10.1002/asia.201101016

  日期：2012.6

  AbstractThe title compounds were prepared by aldol reaction of anisaldehyde and the respective N,N‐dibenzyl glycinates. Deprotection of the nitrogen atom with Pearlman’s catalyst delivered the unprotected β‐hydroxytyrosine esters, which were further N‐protected as N,N‐phthaloyl (Phth) and N‐fluorenylmethylcarbonyloxy (Fmoc) derivatives. The Friedel–Crafts reaction with various arenes was studied employing these alcohols as electrophiles. It turned out that the facial diastereoselectivitiy depends on the nitrogen protecting group and on the ester group. The unprotected substrates (NH2) gave preferentially syn‐products but the anti‐selectivity increased when going from NHFmoc over NPhth to NBn2. If the ester substituent was varied the syn‐preference increased in the order Me <Et <iPr. The reactions were shown to be fully stereoconvergent and proceeded under kinetic product control. A model is suggested to explain the facial diastereoselectivity based on a conformationally locked benzylic cation intermediate. The reactions are preparatively useful for the N‐unprotected isopropyl ester, which gave Friedel–Crafts alkylation products with good syn‐selectivity (anti/syn=21:79 to 7:93), and for the N,N‐dibenzyl‐protected methyl ester, which led preferentially to anti‐products (anti/syn=80:20 to >95:5). Upon acetylation of the latter compound to the respective acetate, Bi(OTf)3‐catalyzed alkylation reactions became possible, in which silyl enol ethers served as nucleophiles. The respective alkylation products were obtained in high yield and with excellent anti‐selectivitiy (anti/syn≥95:5).
• Substituent effects in the reaction of N-benzoyl-.beta.-arylserinates with thionyl chloride
  作者：Seemon H. Pines、Matthew A. Kozlowski

  DOI：10.1021/jo00967a023

  日期：1972.1