tert-Butyl 5α-Iodo-1-methyl<4.4.4.5>fenestrane-7β-carboxylate | 144774-89-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: tert-Butyl 5α-Iodo-1-methyl<4.4.4.5>fenestrane-7β-carboxylate
• CAS: 144774-89-0
• 化学式: C₁₆H₂₃IO₂
• 分子量: 374.262
• InChiKey: JCNOSZMGWKTMME-GEUHORSDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.81
• 重原子数：
  19.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  tert-Butyl 5α-Iodo-1-methyl<4.4.4.5>fenestrane-7β-carboxylate 以 正戊烷 为溶剂， 反应 5.0h， 以84%的产率得到
  参考文献：
  名称：

  Cation, carbene, and radical centers in a [4.4.4.5]Fenestrane

  摘要：

  Carbocation 2a, formed on photolysis of iodide 3a in methanol is captured by solvent to yield 4d exclusively. Carbene 2b, formed on photolysis of salt 1b in methanol, also yields only 4d. Radical 2c, formed on photochemical initiation of reaction between 3a and tributylstannane, abstracts hydrogen without rearrangement to give only 3c. These reactions and relevant MNDO calculations are discussed.

  DOI：

  10.1016/s0040-4020(01)89864-1
• 作为产物：
  描述：

  rac-tert-butyl (1R,3S,4R,5S,6R,8R)-1-methyl-6-(tosyloxy)tetracyclo[6.1.1.03,9.05,9]decane-4-carboxylate 在 magnesium iodide 作用下， 以 乙醚 为溶剂， 反应 1.5h， 以84%的产率得到tert-Butyl 5α-Iodo-1-methyl<4.4.4.5>fenestrane-7β-carboxylate
  参考文献：
  名称：

  Cation, carbene, and radical centers in a [4.4.4.5]Fenestrane

  摘要：

  Carbocation 2a, formed on photolysis of iodide 3a in methanol is captured by solvent to yield 4d exclusively. Carbene 2b, formed on photolysis of salt 1b in methanol, also yields only 4d. Radical 2c, formed on photochemical initiation of reaction between 3a and tributylstannane, abstracts hydrogen without rearrangement to give only 3c. These reactions and relevant MNDO calculations are discussed.

  DOI：

  10.1016/s0040-4020(01)89864-1