(2R)-1-氨基-3-苯氧基-2-丙醇 | 133522-40-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: (2R)-1-氨基-3-苯氧基-2-丙醇
• 中文别名: (2R)-(+)-1-氨基-3-苯氧基-2-丙醇
• 英文名称: (R)-(-)-1-amino-3-phenyloxy-2-propanol
• 英文别名: (R)-1-amino-3-phenoxypropan-2-ol；1-amino-3-phenyloxy-2-propanol；(2R)-1-amino-3-phenoxy-2-propanol；(2R)-1-amino-3-phenoxypropan-2-ol
• CAS: 133522-40-4
• 化学式: C₉H₁₃NO₂
• 分子量: 167.208
• InChiKey: JZEHWMUIAKALDN-MRVPVSSYSA-N

物化性质

• 沸点：
  330.2±27.0 °C(Predicted)
• 密度：
  1.129±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  55.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R)-1-氨基-3-苯氧基-2-丙醇 在 lithium hydroxide monohydrate 、 2,4,6-三氯苯甲酰氯 、 水 、 三乙酰氧基硼氢化钠 、 氟化氢吡啶 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 氯仿 、 水 为溶剂， 反应 31.5h， 生成 (2R,6R,7S,8R,10R,11R,12S,13S,14R)-11-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-7-hydroxy-13-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-10-methoxy-4,6,8,10,12,14-hexamethyl-2-(phenoxymethyl)-1-oxa-4-azacyclopentadecan-15-one
  参考文献：
  名称：

  Synthesis and structure–activity relationship of a novel class of 15-membered macrolide antibiotics known as ‘11a-azalides’

  摘要：

  Macrolide antibiotics are widely prescribed for the treatment of respiratory tract infections; however, the increasing prevalence of macrolide-resistant pathogens is a public health concern. Therefore, the development of new macrolide scaffolds with activities against resistant pathogens is urgently needed. An efficient method for reconstructing the erythromycin A macrolactone skeleton has been established. Based on this methodology, novel 15-membered macrolides, known as '11a-azalides', with substituents at the C12, C13, or C4 '' positions were synthesized and their antibacterial activities were evaluated. These derivatives showed promising antibacterial activities against erythromycin-resistant Streptococcus pneumoniae. Among them, the C4 '' substituted derivatives had the most potent activity against erythromycin-resistant S. pneumoniae. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.08.007
• 作为产物：
  描述：

  (S)-2-acetoxy-1-phenoxy-3-chloropropane 在 potassium tert-butylate 、 氨 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 生成 (2R)-1-氨基-3-苯氧基-2-丙醇
  参考文献：
  名称：

  Enzyme assisted preparation of enantiomerically pure β-adrenergic blockers II. Building blocks of high optical purity and their synthetic conversion

  摘要：

  Based on previous screening results a series of potential building blocks 2-4 for beta-adrenergic blockers were prepared both by enzymatic hydrolysis and acyltransfer and further transformed into the corresponding oxiranes and aminoalcohols of defined absolute configurations.

  DOI：

  10.1016/s0957-4166(00)80191-3

文献信息

• Prodrugs of a 3-(pyrrol-2-ylmethylidene)-2-indolinone derivatives
  申请人：Sugen. Inc.

  公开号：US20030100555A1

  公开（公告）日：2003-05-29

  The present invention relates to pyrrole substituted 2-indolinone compounds and their pharmaceutically acceptable salts which modulate the activity of protein kinases and therefore are expected to be useful in the prevention and treatment of protein kinase related cellular disorders such as cancer.

  本发明涉及吡咯替代的2-吲哚酮化合物及其药学上可接受的盐，这些化合物调节蛋白激酶的活性，因此预计在预防和治疗蛋白激酶相关的细胞疾病，如癌症方面具有用处。
• Pharmaceutically active pyrrolidine derivatives
  申请人：——

  公开号：US20030212012A1

  公开（公告）日：2003-11-13

  The present invention is related to pyrrolidine derivatives of formula (I). Said 1 compounds are preferably for use as pharmaceutically active compounds. Specifically, pyrrolidine derivatives of formula (I) are useful in the treatment and/or prevention of premature labor, premature birth and dysmenorrhea. In particular, the present invention is related to pyrrolidine derivatives displaying a substantial modulatory, notably an antagonist activity of the oxytocin receptor. More preferably, said compounds are useful in the treatment and/or prevention of disease states mediated by oxytocin, including premature labor, premature birth and dysmenorrhea. The present invention is furthermore related to novel pyrrolidine derivatives as well as to methods of their preparation, wherein X is selected from the group consisting of CR6R7, NOR6, NNR6R7; A is selected from the group consisting of —(C═O)—, —(C═O)—O—, —C(═NH)—, —(C═O)—NH—, —(C═S)—NH, —SO22—, —SO2NH—, —CH2—,B is either a group —(C═O)—NR8R9 or represents a heterocyclic residue having the formula (a) wherein Q is NR10, O or S; n is an integer selected of 0, 1 or 2; Y, Z and E form together with the 2 carbons to which they are attached a 5-6 membered aryl or heteroaryl ring.

  本发明涉及式(I)的吡咯烷衍生物。所述化合物优选用作药用活性化合物。具体而言，式(I)的吡咯烷衍生物在治疗和/或预防早产、早产和痛经方面是有用的。特别是，本发明涉及显示出氧催产素受体显著调节作用，特别是拮抗剂活性的吡咯烷衍生物。更具体地，所述化合物在治疗和/或预防由氧催产素介导的疾病状态，包括早产、早产和痛经方面是有用的。本发明还涉及新型吡咯烷衍生物以及其制备方法，其中X从CR6R7、NOR6、NNR6R7组中选择；A从—(C═O)—、—(C═O)—O—、—C(═NH)—、—(C═O)—NH—、—(C═S)—NH、—SO22—、—SO2NH—、—CH2—中选择；B是一个群—(C═O)—NR8R9或表示具有式(a)的杂环残基，其中Q是NR10、O或S；n是选择的整数0、1或2；Y、Z和E与它们连接的2个碳一起形成一个5-6成员芳基或杂芳基环。
• Resolution of β-aminoalcohols and 1,2-diamines using fractional crystallization of diastereomeric salts of dehydroabietic acid
  作者：Zhang Guangyou、Liao Yuquing、Wang Zhaohui、Hiroyuki Nohira、Takuji Hirose

  DOI：10.1016/j.tetasy.2003.08.033

  日期：2003.10

  (S)-(+)-1-Amino-3-phenyloxy-2-propanol, (R)-(−)-2-amino-1-phenylethanol, (S)-(+)-1-amino-2-propanol, (1S,2S)-(+)-2-aminocyclohexanol and (1S,2S)-(+)-1,2-diaminocyclohexane were resolved using dehydroabietic acid. It was shown that good to high enantiomeric purity, between 81∼>99% ee, was obtained and that dehydroabietic acid could be easily and efficiently recovered in a reusable form.

  （S）-（+）-1-氨基-3-苯氧基-2-丙醇，（R）-（-）-2-氨基-1-苯基乙醇，（S）-（+）-1-氨基-2-使用脱氢松香酸拆分丙醇，（1 S，2 S）-（+）-2-氨基环己醇和（1 S，2 S）-（+）-1,2-二氨基环己烷。结果表明，获得了良好的至高的对映体纯度，ee在81-> 99％ee之间，并且脱氢松香酸可以容易地和有效地以可重复使用的形式回收。
• Design, Synthesis and Bioactivities Evaluation of Novel Quinazoline Analogs Containing Oxazole Units
  作者：Xuehui Hou、Jingyu Zhang、Xuan Zhao、Liming Chang、Ping Hu、Hongmin Liu

  DOI：10.1002/cjoc.201400271

  日期：2014.6

  A novel type of quinazoline derivatives, which were designed by the combination of quinazoline as the backbone and oxazole scaffold as the substituent, have been synthesized and their biological activities were evaluated for anti‐proliferative activities and EGFR inhibitory potency. Compound 12b demonstrated the most potent inhibitory activity (IC50=0.95 µmol/L for EGFR), which could be optimized as

  以喹唑啉为骨架，恶唑骨架为取代基，设计合成了一种新型的喹唑啉衍生物，并对其生物学活性进行了抗增殖活性和EGFR抑制能力的评价。化合物12b表现出最强的抑制活性（对EGFR的IC 50 = 0.95 µmol / L），可以在进一步的研究中将其优化为潜在的EGFR抑制剂。合成的喹唑啉类似物和所有中间体的结构通过1 H和13 C NMR，2D NMR光谱，IR光谱和MS光谱确认。
• Non-enzymatic kinetic resolution of β-amino alcohols using C-12 higher carbon sugar as a chiral auxiliary
  作者：Jing-Yu Zhang、Hong-Min Liu、Hai-Wei Xu、Li-Hong Shan

  DOI：10.1016/j.tetasy.2008.01.039

  日期：2008.3

  An efficient non-enzymatic kinetic resolution strategy capable of accessing optically active P-adrenergic antagonists intermediates is reported. The C-12 higher carbon sugar derived from naturally occurring sucrose was employed to probe the kinetic resolution. Excellent enantiomeric excesses (ee >99%) and high yields were obtained under very mild conditions. The chiral auxiliary could be recovered in a high reclaimed ratio (>95%) and reusable form without any decrease of the resolving ability. (C) 2008 Published by Elsevier Ltd.