2-溴乙酸十一烷基酯 | 5458-28-6

• 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
• 中文名称: 2-溴乙酸十一烷基酯
• 英文名称: Bromessigsaeure-undecylester
• 英文别名: Undecyl bromoacetate；undecyl 2-bromoacetate
• CAS: 5458-28-6
• 化学式: C₁₃H₂₅BrO₂
• 分子量: 293.244
• InChiKey: ZKYYTXGLBLLRQL-UHFFFAOYSA-N

物化性质

• 保留指数：
  1788.8

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  16
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2915900090

反应信息

• 作为反应物：
  描述：

  2-吡咯烷酮 、 2-溴乙酸十一烷基酯 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 以35%的产率得到Undecyl 2-(2-oxopyrrolidin-1-yl)acetate
  参考文献：
  名称：

  Synthesis and in Vitro Transdermal Penetration Enhancing Activity of Lactam N-Acetic Acid Esters

  摘要：

  A homologous series of N-acetic acid esters of 2-pyrrolidinone and 2-piperidinone has been prepared and evaluated for its ability to enhance the skin content and flux of hydrocortisone 21-acetate in hairless mouse skin in vitro. Enhancement ratios (ER) were determined for flux (J) 24-hour diffusion cell receptor cell concentrations (Q(24)), and 24-h full-thickness mouse skin steroid content (SC) and compared to control values (no enhancer present). In addition, in an attempt to abrogate toxicity, these dermal penetration enhancers were designed to have the potential for biodegradation by dermal esterases. 2-Oxopyrrolidine-alpha-acetic acid dodecyl ester (5) showed the highest enhancement ratios for J(ER 67.33) and Q(24) (ER 180.66). 2-Oxopipelidine-alpha-acetic acid decyl ester (10) showed a high Q(24) (ER 162.07) but a lower J (ER 12.67). 2-Oxopyrrolidine-alpha-acetic acid decyl ester (3) showed the highest enhancement ratio for SC (ER 8.7). The ER Q(24) for 3, 5 and 10, as well as other lactam N-acetic acid esters in this work, were significantly higher than the ER found using Atone as enhancer.(dagger)

  DOI：

  10.1021/js950331n
• 作为产物：
  描述：

  十一烷醇 、 溴乙酰溴 反应 4.0h， 生成 2-溴乙酸十一烷基酯
  参考文献：
  名称：

  Synthesis and in Vitro Transdermal Penetration Enhancing Activity of Lactam N-Acetic Acid Esters

  摘要：

  A homologous series of N-acetic acid esters of 2-pyrrolidinone and 2-piperidinone has been prepared and evaluated for its ability to enhance the skin content and flux of hydrocortisone 21-acetate in hairless mouse skin in vitro. Enhancement ratios (ER) were determined for flux (J) 24-hour diffusion cell receptor cell concentrations (Q(24)), and 24-h full-thickness mouse skin steroid content (SC) and compared to control values (no enhancer present). In addition, in an attempt to abrogate toxicity, these dermal penetration enhancers were designed to have the potential for biodegradation by dermal esterases. 2-Oxopyrrolidine-alpha-acetic acid dodecyl ester (5) showed the highest enhancement ratios for J(ER 67.33) and Q(24) (ER 180.66). 2-Oxopipelidine-alpha-acetic acid decyl ester (10) showed a high Q(24) (ER 162.07) but a lower J (ER 12.67). 2-Oxopyrrolidine-alpha-acetic acid decyl ester (3) showed the highest enhancement ratio for SC (ER 8.7). The ER Q(24) for 3, 5 and 10, as well as other lactam N-acetic acid esters in this work, were significantly higher than the ER found using Atone as enhancer.(dagger)

  DOI：

  10.1021/js950331n

文献信息

• Piekarski,S. et al., Bulletin de la Societe Chimique de France, 1967, p. 4055 - 4062
  作者：Piekarski,S. et al.

  DOI：——

  日期：——
• Piekarski,S. et al., Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1964, vol. 259, p. 151 - 153
  作者：Piekarski,S. et al.

  DOI：——

  日期：——
• Synthesis and in Vitro Transdermal Penetration Enhancing Activity of Lactam N-Acetic Acid Esters
  作者：Bozena B. Michniak、Mark R. Player、J.Walter Sowell

  DOI：10.1021/js950331n

  日期：1996.2

  A homologous series of N-acetic acid esters of 2-pyrrolidinone and 2-piperidinone has been prepared and evaluated for its ability to enhance the skin content and flux of hydrocortisone 21-acetate in hairless mouse skin in vitro. Enhancement ratios (ER) were determined for flux (J) 24-hour diffusion cell receptor cell concentrations (Q(24)), and 24-h full-thickness mouse skin steroid content (SC) and compared to control values (no enhancer present). In addition, in an attempt to abrogate toxicity, these dermal penetration enhancers were designed to have the potential for biodegradation by dermal esterases. 2-Oxopyrrolidine-alpha-acetic acid dodecyl ester (5) showed the highest enhancement ratios for J(ER 67.33) and Q(24) (ER 180.66). 2-Oxopipelidine-alpha-acetic acid decyl ester (10) showed a high Q(24) (ER 162.07) but a lower J (ER 12.67). 2-Oxopyrrolidine-alpha-acetic acid decyl ester (3) showed the highest enhancement ratio for SC (ER 8.7). The ER Q(24) for 3, 5 and 10, as well as other lactam N-acetic acid esters in this work, were significantly higher than the ER found using Atone as enhancer.(dagger)