6-[(2-苯基乙基)(丙基)氨基]-5,6,7,8-四氢萘-1-酚 | 309757-07-1

• 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
• 中文名称: 6-[(2-苯基乙基)(丙基)氨基]-5,6,7,8-四氢萘-1-酚
• 中文别名: 1-氨基-2-乙基环戊烷羧酸
• 英文名称: (1R,2R)-1-amino-2-ethylcyclopentanecarboxylic acid
• 英文别名: (1R,2R)-1-amino-2-ethylcyclopentane-1-carboxylic acid
• CAS: 309757-07-1
• 化学式: C₈H₁₅NO₂
• 分子量: 157.213
• InChiKey: VFTCZGKOTNJNAW-HTRCEHHLSA-N

物化性质

• 熔点：
  270-271 °C
• 沸点：
  274.1±23.0 °C(Predicted)
• 密度：
  1.087±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  63.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (1S,5R,7R)-7-phenyl-1-vinyl-6-aza-9-oxaspiro[4.5]decan-10-one 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 16.0h， 以88%的产率得到6-[(2-苯基乙基)(丙基)氨基]-5,6,7,8-四氢萘-1-酚
  参考文献：
  名称：

  Diastereoselective Intramolecular Additions of Allyl- and Propargylsilanes to Iminium Ions: Synthesis of Cyclic and Bicyclic Quaternary Amino Acids

  摘要：

  Chiral imino lactones derived from (R)-phenylglycinol containing an allyl- or propargyltrimethylsilyl group in the side chain readily cyclized in the presence of acidic reagents to afford spirocyclic compounds with high diastereoselectivity. Removal of the chiral auxiliary produced 2-substituted 1-aminocycloalkanecarboxylic acids, whereas further cyclizations by means of metathesis or hydroamination reactions led to bicyclic derivatives of pipecolic acid and proline.

  DOI：

  10.1021/ol1010246

文献信息

• Carbocyclic α-amino acids: asymmetric Strecker synthesis of a series of 2-alkylated 1-aminocyclopentanecarboxylic acids
  作者：Judith Wede、Franz-J Volk、August W Frahm

  DOI：10.1016/s0957-4166(00)00284-6

  日期：2000.8

  A series of 12 carbocyclic alpha-amino acids has been prepared from four different racemic 2-alkylated cyclopentanones and (R)-1-phenylethylamine as the chiral auxiliary by means of an asymmetric Strecker synthesis. The stereoselectivity was influenced by solvent, temperature and size of the substituent at the 2-position of the cyclopentanones. For the methyl and ethyl substituted amino acids all four possible stereoisomers could be obtained, whereas for the isopropyl and tertiary butyl compounds an unexpected side reaction prohibited the isolation of the cis configured amino acids. The 1,3-induction mechanism observed for the kinetically controlled alpha-amino nitrile formation in the 2-methyl and 2-ethyl series was overlayed by a 1,2-induction in the respective 2-isopropyl and 2-tertiary butyl series. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Diastereoselective Intramolecular Additions of Allyl- and Propargylsilanes to Iminium Ions: Synthesis of Cyclic and Bicyclic Quaternary Amino Acids
  作者：Santos Fustero、Natalia Mateu、Antonio Simón-Fuentes、José Luis Aceña

  DOI：10.1021/ol1010246

  日期：2010.7.2

  Chiral imino lactones derived from (R)-phenylglycinol containing an allyl- or propargyltrimethylsilyl group in the side chain readily cyclized in the presence of acidic reagents to afford spirocyclic compounds with high diastereoselectivity. Removal of the chiral auxiliary produced 2-substituted 1-aminocycloalkanecarboxylic acids, whereas further cyclizations by means of metathesis or hydroamination reactions led to bicyclic derivatives of pipecolic acid and proline.