trimethylsilyl 4-aminobutanoate | 53611-22-6

• 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: trimethylsilyl 4-aminobutanoate
• CAS: 53611-22-6
• 化学式: C₇H₁₇NO₂Si
• 分子量: 175.303
• InChiKey: NGWBYXYDLMJSND-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  11.0
• 可旋转键数：
  4.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  52.32
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  trimethylsilyl 4-aminobutanoate 、 1,3-二(苄氧羰基)-2-甲基异硫脲 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  从氨基酸实际合成游离和受保护的胍基酸

  摘要：

  在一锅反应中合成了受保护的胍基酸。用二氯甲烷中的三甲基甲硅烷基氯，三乙胺，二碳苯甲氧基-S-甲基异硫脲处理氨基酸，然后通过用甲醇处理除去甲硅烷基，得到相应的碳苯甲酰胍基酸。

  DOI：

  10.1016/0040-4039(96)00299-7
• 作为产物：
  描述：

  三甲基氯硅烷 、 4-氨基丁酸 以 二氯甲烷 为溶剂， 反应 0.17h， 生成 trimethylsilyl 4-aminobutanoate
  参考文献：
  名称：

  N-烷基化亚精胺片段和精胺生物碱苦瓜胺A类似物的简单合成

  摘要：

  通过琥珀酰亚胺基N-三苯甲基-β-丙氨酸酯与三甲基甲硅烷基γ-氨基丁酸酯的偶合可容易地将琥珀酰胺化N-三苯甲基-β-丙氨酰基-γ-氨基丁酸酯和N-三苯甲基-γ-氨基丁酰基-β-丙氨酸酰化各种胺用N-三苯甲基-γ-氨基丁酸和β-丙氨酸甲酯分别还原，然后用LiAlH 4还原，生成N-单烷基化亚精胺片段和精胺生物碱kukoamine A的类似物。该方法在固相上的适用性也是演示。

  DOI：

  10.1016/s0040-4039(00)02308-x

文献信息

• Drug latentiation by .gamma.-glutamyl transpeptidase
  作者：Sanne D. J. Magnan、Frances N. Shirota、Herbert T. Nagasawa

  DOI：10.1021/jm00351a003

  日期：1982.9

  The N-gamma-glutamyl derivatives of L-thiazolidine-4-carboxylic acid, 4-aminobutyric acid, 1-aminocyclopentanecarboxylic acid, 2-aminophenol, and p-fluoro-L-phenylalanine (compounds 6, 8, 9, 10, and 12, respectively) were synthesized using the synthon phthaloylglutamic anhydride. Their relative rates of cleavage by the enzyme gamma-glutamyl transpeptidase (gamma-GT) were determined in order to evaluate

  L-噻唑烷-4-羧酸，4-氨基丁酸，1-氨基环戊烷羧酸，2-氨基苯酚和对氟-L-苯丙氨酸的N-γ-谷氨酰基衍生物（化合物6、8、9、10和使用间苯二甲酰谷氨酸酐合成12）。确定了它们被γ-谷氨酰转肽酶（γ-GT）切割的相对速率，以便评估在某些病理条件下该酶选择性释放的可能性。化合物6、8和9不易被γ-GT溶剂化，但是化合物10和12以及3-和4-氨基苯酚的N-γ-谷氨酰化衍生物易于裂解。
• A new procedure for the conversion of thiols into reactive sulfenylating agents
  作者：D. H. R. Barton、Robert H. Hesse、A. C. O'Sullivan、M. M. Pechet

  DOI：10.1021/jo00023a039

  日期：1991.11

  Thiols may be converted in high yield into unsymmetrical 2-pyridyl disulfides 3. Treatment of these with alkylating agents (e.g., alkyl fluorosulfonates or oxonium salts) affords the corresponding N-alkylpyridyl disulfides 4, which are potent sulfenylating agents (Scheme II) and react smoothly with a variety of sulfur nucleophiles (e.g., thiols, thiones, thioamides, dithiocarbamates, thiocyanate, etc.) to afford disulfides, with amines to afford sulfenamides, and with beta-diketones to afford sulfides. This new method is particularly well-suited to the preparation of unsymmetrical disulfides and sulfenamides from complex and otherwise reactive thiols.
• Betulinic Acid Derivatives:  A New Class of Specific Inhibitors of Human Immunodeficiency Virus Type 1 Entry
  作者：Françoise Soler、Christèle Poujade、Michel Evers、Jean-Christophe Carry、Yvette Hénin、Anne Bousseau、Thierry Huet、Rudi Pauwels、Erik De Clercq、Jean-François Mayaux、Jean-Bernard Le Pecq、Norbert Dereu

  DOI：10.1021/jm950669u

  日期：1996.1.1

  A novel series of omega-aminoalkanoic acid derivatives of betulinic acid were synthesized and evaluated for their activity against human immunodeficiency virus (HIV). The anti-HIV-1 activity of several members of this new series was found to be in the nanomolar range in CEM 4 and MT-4 cell cultures. The optimization of the omega-aminoalkanoic acid side chain is described. The presence of an amide function within the side chain was found important for optimal activity. RPR 103611 (14g), a statine derivative, was found to be inactive against HIV-1 protease, reverse transcriptase, and integrase as well as on gp120/CD4 binding. ''Time of addition'' experiments suggested interaction with an early step of HIV-1 replication. As syncytium formation, but not virus-cell binding, seems to be affected, betulinic acid derivatives are assumed to interact with the postbinding virus-cell fusion process.
• Simple syntheses of N-alkylated spermidine fragments and analogues of the spermine alkaloid kukoamine A
  作者：Stratos Vassis、George Karigiannis、George Balayiannis、Maria Militsopoulou、Petros Mamos、George W Francis、Dionissios Papaioannou

  DOI：10.1016/s0040-4039(00)02308-x

  日期：2001.2

  trimethylsilyl γ-aminobutyrate and of N-trityl-γ-aminobutyric acid with methyl β-alaninate, respectively, followed by LiAlH4 reduction, produced N-monoalkylated spermidine fragments and analogues of the spermine alkaloid kukoamine A. The applicability of this methodology on the solid phase was also demonstrated.

  通过琥珀酰亚胺基N-三苯甲基-β-丙氨酸酯与三甲基甲硅烷基γ-氨基丁酸酯的偶合可容易地将琥珀酰胺化N-三苯甲基-β-丙氨酰基-γ-氨基丁酸酯和N-三苯甲基-γ-氨基丁酰基-β-丙氨酸酰化各种胺用N-三苯甲基-γ-氨基丁酸和β-丙氨酸甲酯分别还原，然后用LiAlH 4还原，生成N-单烷基化亚精胺片段和精胺生物碱kukoamine A的类似物。该方法在固相上的适用性也是演示。
• A practical synthesis of free and protected guanidino acids from amino acids
  作者：Bansi Lal、A.K. Gangopadhyay

  DOI：10.1016/0040-4039(96)00299-7

  日期：1996.4

  Synthesis of protected guanidino acids in one pot reaction is achieved. Amino acids are treated with trimethylsilyl chloride, triethylamine, dicarbobenzoxy-S-methyl isothiourea in dichloromethane followed by removal of silyl group by treatment with methanol to give the corresponding carbobenzoxy guanidino acids.

  在一锅反应中合成了受保护的胍基酸。用二氯甲烷中的三甲基甲硅烷基氯，三乙胺，二碳苯甲氧基-S-甲基异硫脲处理氨基酸，然后通过用甲醇处理除去甲硅烷基，得到相应的碳苯甲酰胍基酸。