(±)-ethyl 2-amino-3-(naphthalen-1-yl)propanoate | 177575-73-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (±)-ethyl 2-amino-3-(naphthalen-1-yl)propanoate
• 英文别名: 2-amino-3-naphthalen-1-yl-propionic acid ethyl ester；Ethyl 2-amino-3-(naphthalen-1-yl)propanoate；ethyl 2-amino-3-naphthalen-1-ylpropanoate
• CAS: 177575-73-4
• 化学式: C₁₅H₁₇NO₂
• mdl: MFCD05228067
• 分子量: 243.305
• InChiKey: GPRJPDYNXGVBNC-UHFFFAOYSA-N

物化性质

• 沸点：
  380.7±22.0 °C(Predicted)
• 密度：
  1.139±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.266
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (±)-ethyl 2-amino-3-(naphthalen-1-yl)propanoate 在 吡啶 、 potassium carbonate 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 34.0h， 生成 (±)-ethyl 2-(N-methylpyridine-2-sulfonamido)-3-(naphthalen-1-yl)propanoate
  参考文献：
  名称：

  Pd-Catalyzed Directed ortho-C–H Alkenylation of Phenylalanine Derivatives

  摘要：

  A practical Pd-catalyzed ortho-olefination of enantioenriched N-(SO2Py)-protected aryl-alanine and norephedrine derivatives with electron-deficient alkenes has been developed using N-fluoro-2,4,6-trimethylpyridinium triflate as the terminal oxidant. The reaction occurs efficiently with excellent monosubstitution selectivity and without loss of enantiopurity. This cross-coupling proved to be broad in scope, tolerating a variety of steric and electronic changes to both coupling partners. Removal of the directing group under mild conditions provides access to optically active tetrahydroisoquinoline-3-carboxylic acid derivatives (Tics) with good diastereocontrol and with very small erosion of enantiomeric purity.

  DOI：

  10.1021/jo502912m
• 作为产物：
  描述：

  ethyl 3-(naphthalen-1-yl)-2-nitroacrylate 在 钯 作用下， 以 甲醇 为溶剂， 25.0 ℃ 、93.33 MPa 条件下， 反应 5.0h， 以The title compound was obtained in 94 mg的产率得到(±)-ethyl 2-amino-3-(naphthalen-1-yl)propanoate
  参考文献：
  名称：

  Arylmethylene Substituted N-Acyl-Beta-Amino Alcohols

  摘要：

  本发明涉及公式I的芳基亚甲基取代的N-酰基-β-氨基醇化合物，其中Y选自芳基或杂芳基基团：R1，R2，R3，R4，R5，Q，X和W的含义如描述中所定义。本发明的化合物是有效的FSH拮抗剂，例如可用于男性或女性的生育控制，或用于骨质疏松症的预防和/或治疗。

  公开号：

  US20090082372A1

文献信息

• Iron-Catalyzed Oxidative CH/CH Cross-Coupling: An Efficient Route to α-Quaternary α-Amino Acid Derivatives
  作者：Kaizhi Li、Guangying Tan、Jingsheng Huang、Feijie Song、Jingsong You

  DOI：10.1002/anie.201306181

  日期：2013.12.2

  Fully loaded: A coordinating activation strategy has been developed to furnish α‐quaternary α‐amino acids through the iron(III)‐catalyzed oxidative functionalization of α‐C(sp3)H bonds of α‐tertiary α‐amino acid esters. The reaction exhibits a broad substrate scope for both α‐amino acids and nucleophiles (Nu) as well as good functional‐group tolerance (see scheme, DTBP=di‐tert‐butyl peroxide, DCE=1

  满负荷：已开发出协调的活化策略，以通过铁（III）催化的α-叔α-氨基酸酯的α-C（sp 3）H键的氧化功能化来提供α-季级α-氨基酸。该反应对α-氨基酸和亲核试剂（Nu）均具有广泛的底物范围，并且具有良好的官能团耐受性（参见方案，DTBP =过氧化二叔丁基，DCE = 1,2-二氯乙烷）。
• Enantioconservative Synthesis of Polysubstituted Pyrimido[4,5-b]azepines
  作者：Dieter Heber、Britta Gerig、Ulrich Girreser、Martin Schütt

  DOI：10.1055/s-0029-1218758

  日期：2010.6

  with amino acids. Subsequent acylation of the uracils by a mixture of acetic anhydride and cyanoacetic acid gave the corresponding 5-cyanoacetylated pyrimidines. In the final step, the pyrimidines were subjected to Dieckmann cyclization with a sodium alcoholate in the corresponding alcohol to afford the corresponding pyrimido[4,5-b]azepines. By using uracils of N-monosubstituted amino acids, cyclization

  开发了用于合成多取代的嘧啶并[4,5- b ] a庚烷的三步对映体保守方案。首先，通过6-氨基酸-1，3-二甲基尿嘧啶的亲核取代合成1，3-二甲基-6- [ N-（2-烷氧基羰基烷基）氨基]尿嘧啶。随后通过乙酸酐和氰基乙酸的混合物将尿嘧啶酰化，得到相应的5-氰基乙酰化的嘧啶。在最后的步骤中，使嘧啶与相应的醇中的乙醇钠进行Dieckmann环化反应，得到相应的嘧啶并[4,5- b ] a庚因。通过使用N的尿嘧啶-单取代的氨基酸，环化与嘧啶环系统的开环结合，得到多取代的氮杂pine。 闭环-杂环-立体选择性合成-嘧啶并氮杂卓-亲核取代
• Arylmethylene Substituted N-Acyl-Beta-Amino Alcohols
  申请人：WORTMANN Lars

  公开号：US20090082372A1

  公开（公告）日：2009-03-26

  The present invention relates to arylmethylene substituted N-Acyl-β-amino alcohols of the formula I in which Y is selected from the aryl or heteroaryl groups: and R1, R2, R3, R4, R5, Q, X and W have the meaning as defined in the description. The compounds according to the invention are effective FSH antagonists and can be used for example for fertility control in men or in women, or for the prevention and/or treatment of osteoporosis.

  本发明涉及公式I的芳基亚甲基取代的N-酰基-β-氨基醇化合物，其中Y选自芳基或杂芳基基团：R1，R2，R3，R4，R5，Q，X和W的含义如描述中所定义。本发明的化合物是有效的FSH拮抗剂，例如可用于男性或女性的生育控制，或用于骨质疏松症的预防和/或治疗。
• [EN] ARYLMETHYLENE SUBSTITUTED N-ACYL-ß-AMINO ALCOHOLS<br/>[FR] N-ACYL-?-AMINO ALCOOLS À SUBSTITUTION ARYLMÉTHYLÈNE
  申请人：BAYER SCHERING PHARMA AG

  公开号：WO2009013354A1

  公开（公告）日：2009-01-29

  The present invention relates to arylmethylene substituted N-Acyl-β-amino alcohols of the formula (I) : in which Y is selected from the aryl or heteroaryl groups: formula (II); and R1, R2, R3, R4, R5, Q, X and W have the meaning as defined in the description. The compounds according to the invention are effective FSH antagonists and can be used for example for fertility control in men or in women, or for the prevention and/or treatment of osteoporosis.
• Arylmethylene substituted N-acyl-beta-amino alcohols
  申请人：Bayer Schering Pharma Aktiengesellschaft

  公开号：EP2018859A1

  公开（公告）日：2009-01-28

  The present invention relates to arylmethylene substituted N-Acyl-β-amino alcohols of the formula I in which Y is selected from the aryl or heteroaryl groups: and R1, R2, R3, R4, R5, Q, X and W have the meaning as defined in the description. The compounds according to the invention are effective FSH antagonists and can be used for example for fertility control in men or in women, or for the prevention and/or treatment of osteoporosis.

  本发明涉及式I的芳基亚甲基取代的N-酰基-β-氨基醇 其中 Y 从芳基或杂芳基中选择: 和 R1、R2、R3、R4、R5、Q、X和W的含义如描述中所定义。 根据本发明的化合物是有效的FSH拮抗剂，例如可用于男性或女性的生育控制，或用于骨质疏松症的预防和/或治疗。