(1S,2S)-(2-dimethylamino-1-phenylpropyl)cyclopentadiene | 169138-82-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1S,2S)-(2-dimethylamino-1-phenylpropyl)cyclopentadiene
• CAS: 169138-82-3
• 化学式: C₁₆H₂₁N
• 分子量: 227.349
• InChiKey: YFKQJAJTQJIJNL-XJKSGUPXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.61
• 重原子数：
  17.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  3.24
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  三甲基氯硅烷 、 (1S,2S)-(2-dimethylamino-1-phenylpropyl)cyclopentadiene 在 正丁基锂 作用下， 生成
  参考文献：
  名称：

  Novel chiral Lewis acids based on a new asymmetric cyclopentadienyl ligand

  摘要：

  The chiral N-functionalized cyclopentadiene ligand Cp(E)H (Cp(E) = C5H4CH(Ph)CH(Me)NMe(2)) was used for the preparation of a series of (transition) metal complexes. Metallation of Cp(E)H is accomplished by reaction with (n)BuLi, K or TlOEt. Reaction of Cp(E)Li with Me(3)SiCl and AlCl3 yields Cp(E)SiMe(3) and Cp(E)AlCl(2) respectively. In the aluminium compound a bidentate coordination of the Cp unit and the nitrogen side-arm is observed. Reaction of Cp(E)SiMe(3) with MCl(4) (M = Ti,Zr) affords Cp(E)MCl(3) in moderate yield. In Cp(E)TiCl(3) the nitrogen side-arm is only weakly coordinated, whereas in Cp(E)ZrCl(3) it is firmly coordinated to the metal centre. Moreover, Cp(E)ZrCl(3) behaves as a moderate Lewis acid, and hitherto catalyzes the Diels-Alder reaction between methacroleine and cyclopentadiene, albeit with no measurable enantiomeric excess.

  DOI：

  10.1016/0022-328x(96)06206-7
• 作为产物：
  描述：

  N-甲基麻黄碱 在 氯化亚砜 、 sodium 作用下， 以 氯仿 为溶剂， 生成 (1S,2S)-(2-dimethylamino-1-phenylpropyl)cyclopentadiene
  参考文献：
  名称：

  A novel chiral cyclopentadienyl ligand based on ephedrine

  摘要：

  natural (-)-(1R,2S)-ephedrine was used as a starting material for the preparation of a novel chiral cyclopentadienyl ligand in a three-step procedure. The new ligand contains a nitrogen atom suitable for chelation to a transition metal, as well as two stereogenic centres.

  DOI：

  10.1016/0957-4166(95)00099-b