(S)-3-氨基-1-苯基-1-丙醇 | 130194-42-2

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: (S)-3-氨基-1-苯基-1-丙醇
• 英文名称: (1S)-3-amino-1-phenyl-1-propanol
• 英文别名: (S)-(-)-3-phenyl-3-hydroxypropylamine；(S)-1-phenyl-3-amino-1-propanol；(S)-3-amino-1-phenyl-1-propanol；(S)-3-amino-1-phenylpropan-1-ol；(S)-3-amino-1-phenylpropanol；(S)-3-amino-1-phenyl-propan-1-ol；(1S)-3-amino-1-phenylpropan-1-ol
• CAS: 130194-42-2
• 化学式: C₉H₁₃NO
• 分子量: 151.208
• InChiKey: PHIYHIOQVWTXII-VIFPVBQESA-N

物化性质

• 熔点：
  53-55 °C
• 沸点：
  293.0±28.0 °C(Predicted)
• 密度：
  1.074±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  46.2
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 海关编码：
  2922199090
• 危险性防范说明：
  P261,P264,P270,P271,P280,P301+P312,P302+P352,P304+P340,P305+P351+P338,P330,P332+P313,P337+P313,P362,P403+P233,P405,P501
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  (S)-3-氨基-1-苯基-1-丙醇 在 lithium aluminium tetrahydride 、 sodium hydride 、 potassium carbonate 作用下， 以 四氢呋喃 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 11.0h， 生成 (3S)-N-甲基-3-苯基-3-[4-(三氟甲基)苯氧基]-1-丙胺盐酸盐(1:1)
  参考文献：
  名称：

  聚合物负载的Ru-TsDPEN催化剂的制备，并用于（S）-氟西汀的对映选择性合成。

  摘要：

  基于Noyori的（1S，2S）-或（1R，2R）-N-（对甲苯磺酰基）-1，2-二苯基乙二胺制备聚合物负载的手性配体9和17。与[RuCl2（p-cymene）] 2的组合已显示出高活性和对映选择性，以甲酸-三乙胺共沸物为氢供体，对芳香族酮（19a-c）进行不对称不对称转移氢化，从而提供了相应的光学异构活性醇20a-c，是手性氟西汀的关键前体。如用于底物19c的配体17所例示的，催化剂可以在三个连续的运行中被回收并重新使用，而对映选择性没有显着下降。该程序避免了有毒的过渡金属物质对氟西汀的合理污染。

  DOI：

  10.1039/b505943g
• 作为产物：
  描述：

  3-azido-1-phenylpropan-1-one 在 alginate immobilized yeast cells 、 palladium (Pd) nanoparticles 作用下， 以 aq. phosphate buffer 为溶剂， 反应 28.0h， 生成 (S)-3-氨基-1-苯基-1-丙醇
  参考文献：
  名称：

  A Green approach towards the synthesis of chiral alcohols using functionalized alginate immobilized Saccharomyces cerevisiae cells

  摘要：

  The stereochemistry of the drug molecule is gaining greater therapeutic importance and thus much attention was drawn in synthesis of chiral compounds by the pharmaceutical industry. In this study Saccharomyces cerevisiae cells immobilized on functionalized alginate beads, catalyze the bio-reduction of prochiral ketones 1a-12a to their corresponding chiral alcohols 1b-12b in higher yields of 60-99% and.excellent optical purity 75-97%. The synthesized chiral azido alcohols 10b-12b were further subjected to hydrogenation using Palladium(Pd) nanoparticles (<= 5 nm), to obtain chiral amino alcohols 10c-12c of therapeutic importance. Thus, a simple, green and inexpensive continuous chemo-enzymatic process has been developed in the synthesis of chiral alcohols/amino alcohols to enhance the scope of the methodology towards industrial application. (C) 2016 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2016.10.016

文献信息

• Catalytic Enantio- and Diastereoselective Alkylations with Cyclic Sulfamidates
  作者：Thomas A. Moss、Beatriz Alonso、David R. Fenwick、Darren J. Dixon

  DOI：10.1002/anie.200905329

  日期：2010.1.12

  Open for business: The enantio‐ and diastereoselective nucleophilic ring opening of five‐membered and six‐membered cyclic sulfamidates under asymmetric phase‐transfer catalysis is presented. A range of pro‐nucleophiles have been successfully alkylated in good yields and in good to excellent enantioselectivites.

  营业时间：介绍了在不对称相转移催化下五元和六元环状氨基磺酸盐的对映体和非对映体选择性亲核开环。一系列亲核亲核试剂已成功烷基化，收率高，对映体选择性优良。
• Scavenger assisted combinatorial process for preparing libraries of amides, carbamates and sulfonamides
  申请人：ELI LILLY AND COMPANY

  公开号：EP0825164A2

  公开（公告）日：1998-02-25

  This invention relates to a novel solution phase process for the preparation of amide, carbamate, and sulfonamide combinatorial libraries. These libraries have utility for drug discovery and are used to form wellplate components of novel assay kits.

  这项发明涉及一种用于制备酰胺、碳酸酯和磺酰胺组合库的新型溶液相过程。这些库在药物发现中具有实用价值，并用于形成新型检测套件的微孔板组件。
• Pharmaceutically active pyrrolidine derivatives as bax inhibitors
  申请人：——

  公开号：US20030171309A1

  公开（公告）日：2003-09-11

  The present invention is related to new substituted pyrrolidine derivatives of formula (I). Said compounds are preferably for use as pharmaceutically active compounds. Specifically, pyrrolidine derivatives of formula (I) are useful in the treatment and/or prevention of neurodegenerative disorders, diseases associated with polygultamine tracts, epilepsy, ischemia, infertility, cardiovascular disorders renal hypoxia, hepatitis and AIDS. Said pyrrolidine derivatives display a modulatory and most notably a down-regulating-up to an inhibitory-activity with respect to the cellular death agonist Bax and/or the activation pathways leading to Bax and allows therefore to block the release of cytochrome (c). The present invention is furthermore related to novel pharmaceutically activity substituted pyrrolidine derivatives as well as to methods of their preparation, wherein X is selected from the group consisting of O, S, CR<6>R<7>, NOR<6>, NNR<6>R<7>; A is selected from the group consisting of —(C═O)—, —(C═O)—O—, —C(═NH)—, —(C═O)—NH—, —(C═S)—NH, —SO2-, —SO2NH—; —CH2-; B is either a group —(C═O)—NR<8>R<9> or represents a heterocyclic residue having the formula (II) wherein Q is NR<10>, 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.

  本发明涉及新的取代吡咯烷衍生物的化学式(I)。所述化合物通常用作药用活性化合物。具体来说，化学式(I)的吡咯烷衍生物在治疗和/或预防神经退行性疾病、与多谷氨酸氨基酸序列相关的疾病、癫痫、缺血、不孕症、心血管疾病、肾脏缺氧、肝炎和艾滋病方面具有用处。所述吡咯烷衍生物显示出对细胞死亡促进子Bax和/或导致Bax激活途径的调节作用，最显著地是下调至抑制活性，并因此允许阻止细胞色素(c)的释放。本发明还涉及新的具有药用活性的取代吡咯烷衍生物，以及它们的制备方法，其中X选自O、S、CR<6>R<7>、NOR<6>、NNR<6>R<7>组成的群；A选自—(C═O)—、—(C═O)—O—、—C(═NH)—、—(C═O)—NH—、—(C═S)—NH、—SO2-、—SO2NH—；—CH2-；B是一个群—(C═O)—NR<8>R<9>或代表具有化学式(II)的杂环残基，其中Q是NR<10>、O或S；n是选自0、1或2的整数；Y、Z和E与它们连接的两个碳共同形成一个5-6成员芳香族或杂芳族环。
• Synthesis of <i>R</i>- and <i>S</i>- Fluoxetine, Norfluoxetine and Related Compounds from Styrene Oxide
  作者：David Mitchell、Thomas M. Koenig

  DOI：10.1080/00397919508012686

  日期：1995.4

  Abstract A facile, high yield synthesis of R—or S—fluoxetine and norfluoxetine is described. This synthetic route utilizes readily available starting materials.

  摘要描述了 R-或 S-氟西汀和去甲氟西汀的简便、高产率合成。该合成路线使用容易获得的起始材料。
• 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。