ethyl 3-amino-3-cyclohexylpropanoate hydrochloride | 100049-94-3

• 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 3-amino-3-cyclohexylpropanoate hydrochloride
• 英文别名: 3-Amino-3-cyclohexyl-propionic acid ethyl ester hydrochloride；ethyl 3-amino-3-cyclohexylpropanoate;hydrochloride
• CAS: 100049-94-3
• 化学式: C₁₁H₂₁NO₂*ClH
• 分子量: 235.754
• InChiKey: VJSABQIJMRZXEH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.27
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  52.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 3-amino-3-cyclohexylpropanoate hydrochloride 在 三乙胺 作用下， 以 甲苯 、 苯 为溶剂， 生成 Ethyl 3-cyclohexyl-3-isocyanatopropanoate
  参考文献：
  名称：

  Organosilicon synthesis of isocyanates: III. Synthesis of aliphatic, carbocyclic, aromatic, and alkylaromatic isocyanatocatboxylic acid esters

  摘要：

  A series of aminoacid esters was prepared by treating the aminoacid suspensions in ethanol with thionyl chloride. Best conversion of aminoacid esters to corresponding isocyanates was achieved in the case of aromatic and carbocyclic aminoesters by phosgeneation of their N-silyl derivatives, and in the case of aliphatic and alkylaromatic aminoesters by phosgeneation of O-silyl or N,O-bissilylurethanes on their basis. In the last case additional step of esterification of the by-products isocyanatoalkylcarboxylic acid chlorides is reqired after phosgeneation. Unusual generation of cynnamates and intramolecular N -> O-migration of trimethylsilyl group in the solutions of silylated alkylaromatic beta-aminoacid esters were found.

  DOI：

  10.1134/s1070363206070115
• 作为产物：
  描述：

  DL-3-氨基-3-苯基丙酸 在 氯化亚砜 、 5% rhodium on activated aluminium oxide 、 氢气 作用下， 以 乙醇 为溶剂， -15.0~80.0 ℃ 、400.01 kPa 条件下， 反应 24.0h， 生成 ethyl 3-amino-3-cyclohexylpropanoate hydrochloride
  参考文献：
  名称：

  Structure Activity Relationships of α_v Integrin Antagonists for Pulmonary Fibrosis by Variation in Aryl Substituents

  摘要：

  Antagonism of alpha(v)beta(6) is emerging as a potential treatment of idiopathic pulmonary fibrosis based on strong target validation. Starting from an alpha(v)beta(3) antagonist lead and through simple variation in the nature and position of the aryl substituent, the discovery of compounds with improved alpha(v)beta(6) activity is described. The compounds also have physicochemical properties commensurate with oral bioavailability and are high quality starting points for a drug discovery program. Compounds 33S and 43E1 are pan av antagonists having ca. 100 nM potency against alpha(v)beta(3), alpha(v)beta(5), alpha(v)beta(6), and av beta 8 in cell adhesion assays. Detailed structure activity relationships with these integrins are described which also reveal substituents providing partial selectivity (defined as at least a 0.7 log difference in pIC(50) values between the integrins in question) for alpha(v)beta(3) and alpha(v)beta(5).

  DOI：

  10.1021/ml5002079

文献信息

• New access to racemic β3-amino acids
  作者：Michał Nejman、Anna Śliwińska、Andrzej Zwierzak

  DOI：10.1016/j.tet.2005.04.077

  日期：2005.8

  A general simple procedure having the potential for large scale preparations of racemic β3-amino acids has been developed. The procedure involves base-catalyzed Michael-type addition of sodium diethyl malonate to N-Boc-α-amidoalkyl-p-tolyl sulfones in tetrahydrofuran. Hydrolysis of the adducts by refluxing with 6 M aqueous hydrochloric acid affords β3-amino acid hydrochlorides in high yield and excellent

  具有用于外消旋β大规模制备的潜在的一般简单的程序3 -氨基酸已经研制成功。该方法包括在四氢呋喃中将碱式催化的丙二酸二乙酯钠的迈克尔型加成到N -Boc-α-酰氨基烷基-对甲苯基砜中。通过用6M盐酸水溶液，得到回流加合物的水解β 3吨以高收率和优异的纯度α-氨基酸盐酸盐。
• Piperazinone derivatives and their uses
  申请人：Laboratoire L. Lafon

  公开号：US06344456B1

  公开（公告）日：2002-02-05

  The invention concerns compounds of formula (I) wherein R1, R2, R3, R4 and R5 are as defined herein. Said compounds are useful in therapy as antithrombotic agents.

  该发明涉及公式（I）中的化合物，其中R1、R2、R3、R4和R5如本文所定义。所述化合物在治疗中作为抗血栓药物是有用的。
• US6344456B1
  申请人：——

  公开号：US6344456B1

  公开（公告）日：2002-02-05
• Organosilicon synthesis of isocyanates: III. Synthesis of aliphatic, carbocyclic, aromatic, and alkylaromatic isocyanatocatboxylic acid esters
  作者：A. V. Lebedev、A. B. Lebedeva、V. D. Sheludyakov、S. N. Ovcharuk、E. A. Kovaleva、O. L. Ustinova

  DOI：10.1134/s1070363206070115

  日期：2006.7

  A series of aminoacid esters was prepared by treating the aminoacid suspensions in ethanol with thionyl chloride. Best conversion of aminoacid esters to corresponding isocyanates was achieved in the case of aromatic and carbocyclic aminoesters by phosgeneation of their N-silyl derivatives, and in the case of aliphatic and alkylaromatic aminoesters by phosgeneation of O-silyl or N,O-bissilylurethanes on their basis. In the last case additional step of esterification of the by-products isocyanatoalkylcarboxylic acid chlorides is reqired after phosgeneation. Unusual generation of cynnamates and intramolecular N -> O-migration of trimethylsilyl group in the solutions of silylated alkylaromatic beta-aminoacid esters were found.
• Structure Activity Relationships of α_v Integrin Antagonists for Pulmonary Fibrosis by Variation in Aryl Substituents
  作者：James Adams、Edward C. Anderson、Emma E. Blackham、Yin Wa Ryan Chiu、Thomas Clarke、Natasha Eccles、Luke A. Gill、Joshua J. Haye、Harvey T. Haywood、Christian R. Hoenig、Marius Kausas、Joelle Le、Hannah L. Russell、Christopher Smedley、William J. Tipping、Tom Tongue、Charlotte C. Wood、Jason Yeung、James E. Rowedder、M. Jonathan Fray、Thomas McInally、Simon J. F. Macdonald

  DOI：10.1021/ml5002079

  日期：2014.11.13

  Antagonism of alpha(v)beta(6) is emerging as a potential treatment of idiopathic pulmonary fibrosis based on strong target validation. Starting from an alpha(v)beta(3) antagonist lead and through simple variation in the nature and position of the aryl substituent, the discovery of compounds with improved alpha(v)beta(6) activity is described. The compounds also have physicochemical properties commensurate with oral bioavailability and are high quality starting points for a drug discovery program. Compounds 33S and 43E1 are pan av antagonists having ca. 100 nM potency against alpha(v)beta(3), alpha(v)beta(5), alpha(v)beta(6), and av beta 8 in cell adhesion assays. Detailed structure activity relationships with these integrins are described which also reveal substituents providing partial selectivity (defined as at least a 0.7 log difference in pIC(50) values between the integrins in question) for alpha(v)beta(3) and alpha(v)beta(5).