己内酰胺-D10 | 169297-53-4

• 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
• 中文名称: 己内酰胺-D10
• 英文名称: ε-caprolactam-2,2,3,3,4,4,5,5,6,6-d10
• 英文别名: ε-caprolactam-D10；caprolactam-d10；epsilon-Caprolactam-D10；3,3,4,4,5,5,6,6,7,7-decadeuterioazepan-2-one
• CAS: 169297-53-4
• 化学式: C₆H₁₁NO
• 分子量: 123.08
• InChiKey: JBKVHLHDHHXQEQ-YXALHFAPSA-N

物化性质

• 熔点：
  67-69°C
• 溶解度：
  氯仿（微溶）、甲醇（微溶）

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  己内酰胺-D10 在 diclazuril 作用下， 以 水 为溶剂， 反应 2.0h， 以68%的产率得到6-aminocaproic-2,2,3,3,4,4,5,5,6,6-d10 acid deuteriochloride
  参考文献：
  名称：

  摘要：

  Gramicidin A (gA) analogues with a biotin attached to the C-terminus by an aminocaproyl linker are used as ion channels in the AMBRI(R) biosensor and are referred to as biotinylated gA. In order to examine the conformation and dynamics of the aminocaproyl linker by H-2 solid-state nuclear magnetic resonance, the synthesis of deuterated aminocaproic acid is required. We report on the synthesis of (D-10)-6-aminocaproic acid from commercially available perdeuterated cyclohexanol and its covalent attachment to the C-terminal group of gA to form gAX(D)XB.

  DOI：

  10.1071/ch01179
• 作为产物：
  描述：

  己内酰胺 在 platinum on activated charcoal 、 氢气 作用下， 以 重水 为溶剂， 以74 %的产率得到己内酰胺-D10
  参考文献：
  名称：

  在温和条件下以 Pt/C 为催化剂合成全氘烷基胺/酰胺

  摘要：

  公开了一种合成全氘烷基酰胺/胺的便捷方法。在温和条件下，可以通过氢-氘 （H/D） 交换方案实现，其中 Pt/C 作为催化剂，D2O 作为氘源。去除或还原乙酰基后，该方案可以提供全氘的伯胺、仲胺和叔胺，这是其他方法难以实现的。

  DOI：

  10.1021/acs.joc.4c00553

文献信息

• Tsuzuki, Hirohisa; Mashimo, Takuya; Mukumoto, Mamoru, Journal of Chemical Research, Miniprint, 1996, # 9, p. 2346 - 2360
  作者：Tsuzuki, Hirohisa、Mashimo, Takuya、Mukumoto, Mamoru、Mataka, Shuntaro、Udagawa, Jun、Tashiro, Masashi

  DOI：——

  日期：——
• 2H NMR evidence for dynamic disorder in human skin induced by the penetration enhancer azone
  作者：F.R. Bezema、E. Marttin、P.E.H. Roemelé、J. Brussee、H.E. Boddé、H.J.M. de Groot

  DOI：10.1016/0584-8539(96)01680-7

  日期：1996.7

  Penetration enhancers mediate trans-dermal drug delivery. The penetration enhancer dodecyl-azacycloheptanone (Azone(R)) was characterized in situ with H-2 NMR on human stratum corneum treated with either uniformly deuterated Azone(R) or penetration enhancer with only the entire chain deuterated, in both cases in propylene glycol. The H-2 NMR spectrum at ambient temperature constitutes a single narrow line only 180 Hz wide. This contrasts with the complex lineshapes 1-25 kHz wide commonly observed for methylene deuterons of lipids in a bilayer gel phase, Hence there is no evidence for differences in orientational behaviour between different deuterons at ambient temperature. The narrow line translates into a low overall order parameter S-CD < 0.0008, for all deuterons, revealing rapid motion of the entire enhancer with correlation times tau(c) much less than 6 x 10(-6) s, in all possible directions. At temperatures of about 150 K a H-2 NMR pattern characteristic for a random isotropic powder was observed on samples of stacked stratum corneum sheets at different orientations with respect to the magnetic field. This provides strong evidence for random isotropic freezing of the Azone(R) molecules upon cooling. The H-2 NMR data suggest than incubation with Azone(R) in propylene glycol provokes dynamic structural disorder of the intercellular lamellar lipid structure throughout the stratum corneum and possibly even the creation of fluid domains involving the intercellular lipids, which may be essential for the penetration enhancing effect.