2'-(3α-Benzyloxy-24-norcholan-23-yl)-4',4'-dimethyl-4',5'-dihydrooxazoline-N-oxide | 139286-83-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 2'-(3α-Benzyloxy-24-norcholan-23-yl)-4',4'-dimethyl-4',5'-dihydrooxazoline-N-oxide
• CAS: 139286-83-2
• 化学式: C₃₅H₅₃NO₃
• 分子量: 535.811
• InChiKey: HRDKMEHLROWHEQ-SEZBDSNNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.36
• 重原子数：
  39.0
• 可旋转键数：
  7.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  44.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2'-(3α-Benzyloxy-24-norcholan-23-yl)-4',4'-dimethyl-4',5'-dihydrooxazoline-N-oxide 在 copper diacetate 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 15.0h， 生成 2'-(3α-benzyloxy-24-norcholan-23-yl)-2',4',4'-trimethyl-4',5'-dihydrooxazoline-N-oxyl
  参考文献：
  名称：

  2′(3α-Benzyloxy-24-norcholan-23-yl)-2′,4′4′-trimethyl-4′,5′-dihydrooxazoline-N-oxyl as a potential spin probe for model membranes

  摘要：

  A new steroidal doxyl (4,4-dimethyloxazolidine-N-oxyl) nitroxide (SDN) viz. 2'-(3 alpha-benzyloxy-24-norcholan-2'-yl) -2',4',4'-trimethyl-4',5'-dihydrooxazoline-N-oxyl has been synthesized. This is expected to have higher mobility over other spin labels reported earlier. The localization of this spin probe in lipid bilayers has been determined using H-1 NMR and P-31 NMR techniques. The alterations induced by dugs in the membrane characteristics such as phase transition and permeability have been investigated using electron paramagnetic resonance (EPR) techniques. The results show the applicability of SDN as a potential spin probes in the study of biomembranes.

  DOI：

  10.1016/0039-128x(94)90005-1
• 作为产物：
  描述：

  石胆酸 在 硼酸 、 silica gel 、 四丁基碘化铵 、 sodium hydride 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 乙醚 、 xylene 为溶剂， 反应 99.0h， 生成 2'-(3α-Benzyloxy-24-norcholan-23-yl)-4',4'-dimethyl-4',5'-dihydrooxazoline-N-oxide
  参考文献：
  名称：

  2′(3α-Benzyloxy-24-norcholan-23-yl)-2′,4′4′-trimethyl-4′,5′-dihydrooxazoline-N-oxyl as a potential spin probe for model membranes

  摘要：

  A new steroidal doxyl (4,4-dimethyloxazolidine-N-oxyl) nitroxide (SDN) viz. 2'-(3 alpha-benzyloxy-24-norcholan-2'-yl) -2',4',4'-trimethyl-4',5'-dihydrooxazoline-N-oxyl has been synthesized. This is expected to have higher mobility over other spin labels reported earlier. The localization of this spin probe in lipid bilayers has been determined using H-1 NMR and P-31 NMR techniques. The alterations induced by dugs in the membrane characteristics such as phase transition and permeability have been investigated using electron paramagnetic resonance (EPR) techniques. The results show the applicability of SDN as a potential spin probes in the study of biomembranes.

  DOI：

  10.1016/0039-128x(94)90005-1

文献信息

• Synthesis of 2'-(3α-benzyloxy-24-norcholan-23-yl)-2',4',4'-trimethyl- 4',5'-dihydrooxazoline-n-oxyl - a new potential spin probe for biomembranes
  作者：Sharmila Banerjee、Umesh R. Desai、Girish K. Trivedi

  DOI：10.1016/s0040-4020(01)80586-x

  日期：1992.1

  The synthesis of a new steroidal nitroxide, viz. 2'-(3α-benzyloxy-24-norcholan-23-yl)-2',4'4'-trimethyl-4',5'- dihydrooxazoline-n-oxyl , a potential spin probe for bio- membranes is described. The title compound in improved yield could be obtained by a direct Grignard reaction on the oxaziridine . This effected a one-step reduction in the overall synthetic sequence. The methodology of the Grignard

  一种新的甾族氮氧化物的合成，即。描述了2'-（3α-苄氧基-24-降胆固醇23-基）-2'，4'4'-三甲基-4'，5'-二氢恶唑啉-n-氧基，它是生物膜的潜在自旋探针。通过在吡唑烷上直接进行格氏反应，可以得到产率提高的标题化合物。这实现了整个合成序列的一步减少。首次报道了在吡唑烷上进行格氏反应以生成氮氧化物的方法。在稀溶液中，已经测量了各向同性的ESR参数。