(1aR,4R,4aR,7R,7aS,7bS)-1,1,7-trimethyl-4-((phenylselanyl)methyl)decahydro-1H-cyclopropa[e]azulen-4-ol | 1114568-41-0

• 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: (1aR,4R,4aR,7R,7aS,7bS)-1,1,7-trimethyl-4-((phenylselanyl)methyl)decahydro-1H-cyclopropa[e]azulen-4-ol
• CAS: 1114568-41-0
• 化学式: C₂₁H₃₀OSe
• 分子量: 377.429
• InChiKey: ZZJGGEWCAQLJMJ-KRUMZEMCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.89
• 重原子数：
  23.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (1aR,4R,4aR,7R,7aS,7bS)-1,1,7-trimethyl-4-((phenylselanyl)methyl)decahydro-1H-cyclopropa[e]azulen-4-ol 在 ammonium peroxydisulfate 、 水 作用下， 以 乙腈 为溶剂， 以8%的产率得到(1S,2S,4R,7R,8R,11R)-3,3,11-trimethyl-7-hydroxymethyl-tricyclo<6.3.0.0^2,4>undecan-7-ol
  参考文献：
  名称：

  Diastereo and Enantioselective Synthesis of 1,2-Diols Promoted by Electrophilic Selenium Reagents

  摘要：

  Here we report the first example in which the phenylseleno group is directly substituted by a hydroxy function. The reaction is promoted by the PhSeOSO3H generated "in situ" by oxidation of (PhSe)(2) with (NH4)(2)S2O8 at reflux in a 3:1 mixture of MeCN-H2O. Interestingly the reaction can be performed in "one pot" using a catalytic amount of diselenide affording the corresponding diols (5 and 6) with good yield and good level of diastereo- and enantioselectivity.

  DOI：

  10.1080/10426500801900881
• 作为产物：
  描述：

  (+)-香橙烯 、 苯基硒基三氟甲烷磺酸酯 在 水 作用下， 以 乙腈 为溶剂， 反应 40.0h， 以56%的产率得到(1aR,4S,4aR,7R,7aS,7bS)-1,1,7-trimethyl-4-((phenylselanyl)methyl)decahydro-1H-cyclopropa[e]azulen-4-ol
  参考文献：
  名称：

  Diastereo and Enantioselective Synthesis of 1,2-Diols Promoted by Electrophilic Selenium Reagents

  摘要：

  Here we report the first example in which the phenylseleno group is directly substituted by a hydroxy function. The reaction is promoted by the PhSeOSO3H generated "in situ" by oxidation of (PhSe)(2) with (NH4)(2)S2O8 at reflux in a 3:1 mixture of MeCN-H2O. Interestingly the reaction can be performed in "one pot" using a catalytic amount of diselenide affording the corresponding diols (5 and 6) with good yield and good level of diastereo- and enantioselectivity.

  DOI：

  10.1080/10426500801900881