(S)-4-[4-(2-Methoxy-acryloyloxy)-benzyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester | 143817-59-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: (S)-4-[4-(2-Methoxy-acryloyloxy)-benzyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl (4S)-4-[[4-(2-methoxyprop-2-enoyloxy)phenyl]methyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
• CAS: 143817-59-8
• 化学式: C₂₁H₂₉NO₆
• 分子量: 391.464
• InChiKey: WCAORJZOBVJNRL-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  74.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-4-[4-(2-Methoxy-acryloyloxy)-benzyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 在 甲醇 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 Tebbe's reagent 、 偶氮二异丁腈 、 四丁基氟化铵 、 三正丁基氢锡 、 碳酸氢钠 、 对甲苯磺酸 、 di(1H-imidazol-2-yl)methanethione 、 三乙胺 、 三氟乙酸 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 生成 ((S)-2-{3-[4-((S)-2-Benzyloxycarbonylamino-3-hydroxy-propyl)-phenoxy]-4-methoxy-phenyl}-1-hydroxymethyl-ethyl)-carbamic acid benzyl ester
  参考文献：
  名称：

  Synthesis of (S,S)-isodityrosinol in a fully differentiated form via Diels-Alder methodology

  摘要：

  A Diels-Alder cycloaddition reaction of an aryloxy diene 7 and an acetylenic ketone 8 derived, respectively, from L-tyrosine and D-serine leads to the synthesis of the diaryl ether unit common to isodityrosine, which upon elaboration provides the functionally differentiated (S,S)-isodityrosinol 15.

  DOI：

  10.1021/jo00048a005
• 作为产物：
  描述：

  N-[(1S)-2-羟基-1-[(4-羟基苯基)甲基]乙基]-氨基甲酸1,1-二甲基乙基酯 在 4-二甲氨基吡啶 、 对甲苯磺酸 、 N,N'-二环己基碳二亚胺 作用下， 以 丙酮 为溶剂， 生成 (S)-4-[4-(2-Methoxy-acryloyloxy)-benzyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Synthesis of (S,S)-isodityrosinol in a fully differentiated form via Diels-Alder methodology

  摘要：

  A Diels-Alder cycloaddition reaction of an aryloxy diene 7 and an acetylenic ketone 8 derived, respectively, from L-tyrosine and D-serine leads to the synthesis of the diaryl ether unit common to isodityrosine, which upon elaboration provides the functionally differentiated (S,S)-isodityrosinol 15.

  DOI：

  10.1021/jo00048a005

文献信息

• Synthesis of Functionalized Aryloxy 1,3-Butadienes and Their Transformation to Diaryl Ethers via Diels-Alder Cycloaddition Reactions
  作者：Richard K. Olsen、Xianqi Feng、Magnus Campbell、Rui-lian Shao、Shivanand K. Math

  DOI：10.1021/jo00124a010

  日期：1995.9

  The Diels-Alder reaction involving cycloaddition of aryloxy-substituted 1,3-butadienes with appropriate acetylenic electrophiles, followed by aromatization of the newly formed cyclohexadiene ring, has been used for the synthesis of diaryl ethers. The functionalized aryloxy 1,3-butadienes employed in this study were prepared by either of two methods: (1) methylenation of aryl esters via the Tebbe or related reagents, and (2) from 1-(aryloxy)-2-propanone by a sequence of formylation or alkylthio methlylenation, and subsequent enolsilylation. A tetrasubstituted butadiene containing two phenoxy groups at the 1 and 3 positions also was prepared by the latter method. The cycloaddition reactions of 2,3-dioxy-substituted dienes occurred in high yield, but, as expected, with no regioselectivity to furnish nearly equal mixtures of regioisomeric cycloadducts. In contrast, application of 1,2,3-trihetero-substituted dienes resulted in regiospecific cycloaddition reactions. Transformation of the cyclohexadiene cycloadducts to an aromatic ring was accomplished by dehydrogenation with DDQ or by elimination during the cycloaddition process of a molecule of an alkyl mercaptan. A chiral acetylenic ketone derived from D- or L-serine underwent condensation, without racemization, with aryloxy dienes to provide diaryl ethers related to the isodityrosine antibiotics.
• Synthesis of (S,S)-isodityrosinol in a fully differentiated form via Diels-Alder methodology
  作者：Xianqi Feng、Richard K. Olsen

  DOI：10.1021/jo00048a005

  日期：1992.10

  A Diels-Alder cycloaddition reaction of an aryloxy diene 7 and an acetylenic ketone 8 derived, respectively, from L-tyrosine and D-serine leads to the synthesis of the diaryl ether unit common to isodityrosine, which upon elaboration provides the functionally differentiated (S,S)-isodityrosinol 15.