3-amino-1-phenylpropan-1-one hydrochloride | 7495-58-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-amino-1-phenylpropan-1-one hydrochloride
• 英文别名: 3-aminium chloro-1-phenylpropan-1-one；3-Amino-1-phenyl-propan-1-on; Hydrochlorid；3-oxo-3-phenylpropan-1-aminium chloride；3-Oxo-3-phenylpropan-1-aminium chloride；(3-oxo-3-phenylpropyl)azanium;chloride
• CAS: 7495-58-1
• 化学式: C₉H₁₁NO*ClH
• 分子量: 185.653
• InChiKey: SRKNYRPFYRZTOM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.64
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  43.1
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 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,H312,H315,H319,H332,H335
• 储存条件：
  应存放在室温、密封、干燥且惰性气体环境中。

反应信息

• 作为反应物：
  描述：

  二氟乙酸乙酯 、 3-amino-1-phenylpropan-1-one hydrochloride 在 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 14.0h， 以85%的产率得到2,2-difluoro-N-(3-oxo-3-phenylpropyl)acetamide
  参考文献：
  名称：

  Induction of apoptosis promoted by Bang52; a small molecule that downregulates Bcl-xL

  摘要：

  Cancer cells evade death by over-producing specific proteins that inhibit apoptosis. One such group of proteins is the Bcl-2 family, of which Bcl-x(L) is an important member. This protein binds and inhibits BAK, another protein that promotes apoptosis. While the development of chemical inhibitors that block Bcl-x(L)-BAK association have been the focus of intense research efforts, we demonstrate in this manuscript an alternative strategy to downregulate Bcl-x(L). We have identified a small molecule (Bang52) that induces apoptosis in a lymphoblast-derived cell line by lowering levels of Bcl-x(L). Since Bang52 bears no resemblance to any chemical binder of Bcl-x(L) we believe that degradation of the protein is stimulated by a new type of pathway. These findings highlight a novel approach to the development of small molecules that promote apoptosis. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.03.067
• 作为产物：
  描述：

  (3-氧代-3-苯丙基)氨基甲酸叔丁酯 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 0.5h， 以75%的产率得到3-amino-1-phenylpropan-1-one hydrochloride
  参考文献：
  名称：

  Induction of apoptosis promoted by Bang52; a small molecule that downregulates Bcl-xL

  摘要：

  Cancer cells evade death by over-producing specific proteins that inhibit apoptosis. One such group of proteins is the Bcl-2 family, of which Bcl-x(L) is an important member. This protein binds and inhibits BAK, another protein that promotes apoptosis. While the development of chemical inhibitors that block Bcl-x(L)-BAK association have been the focus of intense research efforts, we demonstrate in this manuscript an alternative strategy to downregulate Bcl-x(L). We have identified a small molecule (Bang52) that induces apoptosis in a lymphoblast-derived cell line by lowering levels of Bcl-x(L). Since Bang52 bears no resemblance to any chemical binder of Bcl-x(L) we believe that degradation of the protein is stimulated by a new type of pathway. These findings highlight a novel approach to the development of small molecules that promote apoptosis. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.03.067

文献信息

• [EN] INHIBITORS OF AKT ACTIVITY<br/>[FR] INHIBITEURS DE L'ACTIVITE D'AKT
  申请人：MERCK & CO INC

  公开号：WO2005100356A1

  公开（公告）日：2005-10-27

  The present invention is directed to compounds which contain substituted napthyridines which inhibit the activity of Akt, a serine/threonine protein kinase. The invention is further directed to chemotherapeutic compositions containing the compounds of this invention and methods for treating cancer comprising administration of the compounds of the invention.

  本发明涉及含有取代萘啶的化合物，其抑制Akt蛋白激酶的活性。该发明进一步涉及含有本发明化合物的化疗组合物，以及包括给予本发明化合物的方法来治疗癌症。
• Asymmetric Hydrogenation of α, β, and γ-Aminoketones Catalyzed by Cationic Rhodium(I){AMPP} Complexes
  作者：Marc Devocelle、Francine Agbossou、André Mortreux

  DOI：10.1055/s-1997-1004

  日期：1997.11

  The chiral cationic rhodium aminophosphine-phosphinite complexes 4-6 were applied successfully in the asymmetric hydrogenation of α- (7-9), β- (10, 11) and γ- (12) aminoketone hydrochloride derivatives leading to the corresponding aminoalcohols in up to 97, 93, and 92 % enantiomeric excesses for the three types of substrates respectively.

  手性阳离子铑氨基膦-膦配合物 4-6 成功地应用于 δ- (7-9)、δ- (10, 11) 和 δ³- (12) 氨基酮盐酸盐衍生物的不对称氢化反应，得到相应的氨基醇，三种底物的对映体过量率分别高达 97%、93% 和 92%。
• Inhibitors of Akt Activity
  申请人：Bilodeau Mark T.

  公开号：US20080280899A1

  公开（公告）日：2008-11-13

  The present invention is directed to compounds which contain substituted napthyridines which inhibit the activity of Akt, a serine/threonine protein kinase. The invention is further directed to chemotherapeutic compositions containing the compounds of this invention and methods for treating cancer comprising administration of the compounds of the invention.

  本发明涉及含有取代萘啶的化合物，其抑制Akt，一种丝氨酸/苏氨酸蛋白激酶的活性。本发明还涉及包含该发明化合物的化疗组合物以及使用该发明化合物治疗癌症的方法。
• Inhibitors of Akt activity
  申请人：Merck Sharp & Dohme Corp.

  公开号：US07750151B2

  公开（公告）日：2010-07-06

  The present invention is directed to compounds which contain substituted napthyridines which inhibit the activity of Akt, a serine/threonine protein kinase. The invention is further directed to chemotherapeutic compositions containing the compounds of this invention and methods for treating cancer comprising administration of the compounds of the invention.

  本发明涉及含有取代萘啶的化合物，其抑制Akt，一种丝氨酸/苏氨酸蛋白激酶的活性。本发明还涉及包含本发明化合物的化疗组合物以及治疗癌症的方法，包括给予本发明化合物的治疗方法。
• Friedel–Crafts Acylation of Aminocarboxylic Acids in Strong Brønsted Acid Promoted by Lewis Base P₄O₁₀
  作者：Hao Wu、Akinari Sumita、Yuko Otani、Tomohiko Ohwada

  DOI：10.1021/acs.joc.2c01761

  日期：2022.11.18

  (triflic acid, TfOH) if the Lewis base P4O10 is added. Here we describe the Friedel–Crafts acylation reactions of anthranilic acid and α- to δ-aminocarboxylic acids with benzene derivatives in the presence of P4O10. Non-amino-containing carboxylic acids as well as N-containing heteroaromatic carboxylic acids are available, and α-amino acids can be directly utilized without any protective group. Most substrates

  氨基羧酸中的氨基具有足够的碱性，可以在强酸中质子化，因此，由于电荷-电荷排斥，羧酸向酰基离子的电离被阻止。因此，芳香族化合物的酰化在 Friedel-Craft 型反应中显着延迟。我们发现，如果添加路易斯碱 P 4 O 10 ，即使在强布朗斯台德酸（三氟甲磺酸，TfOH）中，氨基羧酸的 Friedel-Crafts 酰化也可以顺利进行。在这里，我们描述了邻氨基苯甲酸和 α- 到 δ-氨基羧酸与苯衍生物在 P 4 O 10存在下的 Friedel-Crafts 酰化反应. 既有不含氨基的羧酸，也有含N的杂芳族羧酸，α-氨基酸可直接使用，无需任何保护基团。尽管可能会发生一些差向异构化/外消旋化，但大多数底物都能提供高产率的酰化产物。密度泛函理论 (DFT) 计算表明 P 4 O 10中和质子化胺，将 N-H 共价键转化为 N-氢键，并使羧酸 OH 官能团充当良好的离去基团。