(+)-(R)-1-hydroxymethyl-2-methylruthenocene | 289057-29-0

• 分子结构分类: 有机化合物 - 碳氢化合物 - 芳香烃
• 英文名称: (+)-(R)-1-hydroxymethyl-2-methylruthenocene
• 英文别名: Cyclopentadienyl[1-(hydroxymethyl)-2-methylcyclopentadienyl] ruthenium；cyclopenta-1,3-diene;(2-methylcyclopenta-2,4-dien-1-yl)methanol;ruthenium(2+)
• CAS: 289057-29-0
• 化学式: C₁₂H₁₄ORu
• 分子量: 275.313
• InChiKey: JCUCJQRVLNAJBF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.61
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+)-(R)-1-hydroxymethyl-2-methylruthenocene 、 碘 以 四氯化碳 为溶剂， 以99%的产率得到
  参考文献：
  名称：

  Enantiomeric haloruthenocenium salts: synthesis of the first representatives with the use of asymmetric reduction and asymmetric cyclopalladation

  摘要：

  Optically active substituted ruthenocenes, (+)-RcCH(OH)Ph (I), (-)-RcCH(Me)Ph (+) and (+)-1-hydroxymethyl-2-methylruthenocene (VIII) react with molecular iodine to yield the corresponding iodoruthenocenium salts Ia, IIa, VIIIa with I-3(-) anions. Reduction of these salts using, for example, NaBH4 regenerates the optically active starting compounds. Ruthenocenes with electron-withdrawing substituents (COMe, COPh, COOMe) remain intact when treated with I-2, Fe(III), or Ce(IV). Asymmetric cyclopalladation of RcCH(2)NMe(2) is described for the first time as the initial step of the reaction sequence leading to (+)-VIII.

  DOI：

  10.1016/s0022-328x(96)06335-8
• 作为产物：
  描述：

  在 sodium tetrahydroborate 作用下， 以 乙腈 为溶剂， 生成 (+)-(R)-1-hydroxymethyl-2-methylruthenocene
  参考文献：
  名称：

  Enantiomeric haloruthenocenium salts: synthesis of the first representatives with the use of asymmetric reduction and asymmetric cyclopalladation

  摘要：

  Optically active substituted ruthenocenes, (+)-RcCH(OH)Ph (I), (-)-RcCH(Me)Ph (+) and (+)-1-hydroxymethyl-2-methylruthenocene (VIII) react with molecular iodine to yield the corresponding iodoruthenocenium salts Ia, IIa, VIIIa with I-3(-) anions. Reduction of these salts using, for example, NaBH4 regenerates the optically active starting compounds. Ruthenocenes with electron-withdrawing substituents (COMe, COPh, COOMe) remain intact when treated with I-2, Fe(III), or Ce(IV). Asymmetric cyclopalladation of RcCH(2)NMe(2) is described for the first time as the initial step of the reaction sequence leading to (+)-VIII.

  DOI：

  10.1016/s0022-328x(96)06335-8