N-Boc-2-(4-甲氧基苯基)-2-羟基乙胺 | 126395-30-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: N-Boc-2-(4-甲氧基苯基)-2-羟基乙胺
• 中文别名: [2-羟基-2-(4-甲氧基-苯基)-乙基]-氨基甲酸叔丁酯
• 英文名称: [2-Hydroxy-2-(4-methoxy-phenyl)-ethyl]-carbamic acid tert-butyl ester
• 英文别名: tert-Butyl (2-hydroxy-2-(4-methoxyphenyl)ethyl)carbamate；tert-butyl N-[2-hydroxy-2-(4-methoxyphenyl)ethyl]carbamate
• CAS: 126395-30-0
• 化学式: C₁₄H₂₁NO₄
• 分子量: 267.325
• InChiKey: ASCGHPKBVNJCGC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  67.8
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2924299090

反应信息

• 作为反应物：
  描述：

  N-Boc-2-(4-甲氧基苯基)-2-羟基乙胺 、 三溴化硼 生成 tert-butyl (2-hydroxy-2-(4-hydroxyphenyl)ethyl)carbamate
  参考文献：
  名称：

  SIMAMOTO, KEHJKO;OFUNEH, YASUSI

  摘要：

  DOI：
• 作为产物：
  描述：

  5-(4-methoxy-phenyl)-oxazolidin-2-one 、 氢氧化钡 生成 N-Boc-2-(4-甲氧基苯基)-2-羟基乙胺
  参考文献：
  名称：

  SIMAMOTO, KEHJKO;OFUNEH, YASUSI

  摘要：

  DOI：

文献信息

• Asymmetric aminohydroxylation of substituted styrenes: applications in the synthesis of enantiomerically enriched arylglycinols and a diamine
  作者：Peter O’Brien、Simon A. Osborne、Daniel D. Parker

  DOI：10.1039/a803821j

  日期：——

  The catalytic asymmetric aminohydroxylation of a variety of styrene derivatives and vinyl aromatics using osmium tetroxide in conjunction with alkaloid-derived ligands [e.g. (DHQ)2PHAL or (DHQD)2PHAL] and haloamine salts of alkyl carbamates (e.g. ethyl carbamate or tert-butyl carbamate) has been investigated. By observing the effect of different aromatic substituents and alkyl carbamates on the regioselectivity, yield and enantioselectivity of the aminohydroxylation reactions, a number of conclusions have been reached: (i) the 1-aryl-2-hydroxyethylamine regioisomers were obtained as the major products in reasonable yield and high (87%) enantiomeric excess; (ii) tert-butyl carbamate was superior to ethyl carbamate in terms of yield, enantioselectivity and ease of removal of the N-protecting group; (iii) high (96%) enantioselectivity was observed with a 4-methoxy-substituted styrene whereas ortho-substituted styrenes gave lower enantioselectivities; (iv) chiral ligands (DHQ)2PHAL and (DHQD)2PHAL gave essentially equal and opposite senses and degrees of asymmetric induction; (v) regioselectivity was ligand dependent with better regioselectivity (and therefore higher isolated yields) obtained with (DHQ)2PHAL than with (DHQD)2PHAL. The products of the aminohydroxylation reactions were used to prepare enantiomerically enriched arylglycinols and a chiral diamine.

  研究人员使用四氧化锇与生物碱衍生配体[如 (DHQ)2PHAL 或 (DHQD)2PHAL] 以及氨基甲酸烷基酯的卤胺盐（如氨基甲酸乙酯或氨基甲酸叔丁酯）共同催化多种苯乙烯衍生物和乙烯基芳烃的不对称氨基羟基化反应。通过观察不同芳香取代基和烷基氨基甲酸酯对氨基羟化反应的区域选择性、产率和对映选择性的影响，得出了一些结论：(i) 主要产物为 1-芳基-2-羟乙基胺，产率合理，对映体过量率高（87%）；(ii) 氨基甲酸叔丁酯在产率、对映体选择性和 N-保护基的易去除性方面优于氨基甲酸乙酯；(iii) 4-甲氧基取代苯乙烯的对映选择性高（96%），而正交取代苯乙烯的对映选择性较低；(iv) 手性配体(DHQ)2PHAL 和(DHQD)2PHAL 的不对称诱导作用和程度基本相同；(v) 区域选择性与配体有关，(DHQ)2PHAL 比 (DHQD)2PHAL 的区域选择性更好（因此分离产率更高）。氨基羟化反应的产物被用于制备对映体富集的芳基甘氨醇和手性二胺。
• Asymmetric aminohydroxylation of substituted styrenes using t-butyl carbamate
  作者：Peter O'Brien、Simon A. Osborne、Daniel D. Parker

  DOI：10.1016/s0040-4039(98)00665-0

  日期：1998.6

  A variety of substituted styrenes have been aminohydroxylated using t-butyl carbamate to give either enantiomer of highly enantiomerically enriched N-Boc protected amino alcohols in good yields. Better levels of regioselectivity were observed with (DHQ)(2)PHAL than with (DHQD)(2)PHAL even though the enantioselectivities observed were comparable. One of the amino alcohol products was converted into a novel chiral diamine. (C) 1998 Elsevier Science Ltd. All rights reserved.