(2R)-N-ethoxycarbonyl-2-phenyl-2-hydroxyethylamine | 144372-49-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2R)-N-ethoxycarbonyl-2-phenyl-2-hydroxyethylamine
• 英文别名: ethyl N-[(2R)-2-hydroxy-2-phenylethyl]carbamate
• CAS: 144372-49-6
• 化学式: C₁₁H₁₅NO₃
• 分子量: 209.245
• InChiKey: QXOFNLAUYSWAST-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  15
• 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：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R)-N-ethoxycarbonyl-2-phenyl-2-hydroxyethylamine 在 氢氧化钾 作用下， 以 甲醇 、 水 为溶剂， 反应 40.0h， 生成 (S)-2-氨基-1-苯乙醇 、 (R)-α-(氨基甲基)苄醇
  参考文献：
  名称：

  Kanerva, Liisa T.; Rahiala, Katri; Vaenttinen, Eero, Journal of the Chemical Society. Perkin transactions I, 1992, # 14, p. 1759 - 1762

  摘要：

  DOI：
• 作为产物：
  描述：

  α-(ethoxycarbonylamino)acetophenone 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 6.0h， 生成 (2R)-N-ethoxycarbonyl-2-phenyl-2-hydroxyethylamine
  参考文献：
  名称：

  Baker’s Yeast Reduction ofα-(Acylamino)acetophenones and Lipase Catalyzed Resolution of 2-Acylamino-1-arylethanols

  摘要：

  使用发酵的面包酵母对α-酰氨基苯乙酮进行酶促还原，得到了光学活性的(R)-2-酰氨基-1-芳基乙醇。进一步地，使用醋酸乙烯酯作为酰基供体，通过脂肪酶催化的拆分反应，生成了(S)-1-乙酰氧基-2-酰氨基-1-芳基乙醇和(R)-2-酰氨基-1-芳基乙醇。

  DOI：

  10.1246/bcsj.66.1216

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.
• AMINOALCOHOL DERIVATIVES
  申请人：Astellas Pharma Inc.

  公开号：EP1697301A2

  公开（公告）日：2006-09-06
• [EN] AMINOALCOHOL DERIVATIVES<br/>[FR] DERIVES D'AMINO-ALCOOLS
  申请人：FUJISAWA PHARMACEUTICAL CO

  公开号：WO2005061433A2

  公开（公告）日：2005-07-07

  The present invention relates to a compound formula (I): wherein (II) is (III) or (IV), X is bond, -CH2-, -O- or -NH-, R1 and R12 are each independently hydrogen, halogen, lower alkyl, etc., R2 is hydrogen or optionally substituted lower alkyl, R3 is hydrogen or an amino protective group, R4, R5 and R6 are each independently hydrogen or optionally substituted lower alkyl, R7 is -Z-R13, in which Z is bond, etc., and R13 is carboxy, lower alkoxycarbonyl, (lower alkylsulfonyl) carbamoyl or lower alkanoylsulfamoyl, R8 is -Y-R9, in which Y is bond, -CH2-, -O-, -S-, etc., and R9 is hydrogen, lower alkyl, cyclo (lower) alkyl, etc., and R11 is hydrogen, lower alkyl, lower alkoxy, etc., or a salt thereof. The compound (I) of the present invention and pharmaceutically acceptable salts thereof are useful for the prophylactic and/or the therapeutic treatment of pollakiurea or urinary incontinence.
• Baker’s Yeast Reduction of<i>α</i>-(Acylamino)acetophenones and Lipase Catalyzed Resolution of 2-Acylamino-1-arylethanols
  作者：Taeko Izumi、Katsumi Fukaya

  DOI：10.1246/bcsj.66.1216

  日期：1993.4

  Enzymatic reduction of α-acylaminoacetophenones with fermenting baker’s yeast afforded optically active (R)-2-acylamino-1-arylethanols. Furthermore, lipase-catalyzed resolution of the 2-acylamino-1-arylethanols using vinyl acetate as an acyl donor resulted in the formation of (S)-1-acetoxy-2-acylamino-1-arylethanols and (R)-2-acylamino-1-arylethanols.

  使用发酵的面包酵母对α-酰氨基苯乙酮进行酶促还原，得到了光学活性的(R)-2-酰氨基-1-芳基乙醇。进一步地，使用醋酸乙烯酯作为酰基供体，通过脂肪酶催化的拆分反应，生成了(S)-1-乙酰氧基-2-酰氨基-1-芳基乙醇和(R)-2-酰氨基-1-芳基乙醇。