α,α-dideutero-N-benzoylmethyl-2-iodo-N-methylbenzylamine | 220474-74-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: α,α-dideutero-N-benzoylmethyl-2-iodo-N-methylbenzylamine
• 英文别名: 2-[[dideuterio-(2-iodophenyl)methyl]-methylamino]-1-phenylethanone
• CAS: 220474-74-8
• 化学式: C₁₆H₁₆INO
• 分子量: 367.198
• InChiKey: KDXXKRDIWCJPRK-ZWGOZCLVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.61
• 重原子数：
  19.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  20.31
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  α,α-dideutero-N-benzoylmethyl-2-iodo-N-methylbenzylamine 在 正丁基锂 作用下， 以60%的产率得到1,1-dideutero-4-hydroxy-2-methyl-4-phenyl-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  Stereoselective Intermolecular Hydride Shift Mechanism of the New Reduction of Benzylic Alcohols with Acid

  摘要：

  A stereoselective intermolecular hydride shift mechanism of the new reduction reaction of the benzylic hydroxy group of 4-hydroxy-4-phenyl-1,2,3,4-tetrahydroisoquinoline (1) to the corresponding alkane (2) with acid was proved by reaction of the deuterated derivatives (5 and 6) of 1.

  DOI：

  10.3987/com-98-8329
• 作为产物：
  描述：

  2-iodobenzaldehyde-α-d₁ 在 硼氘化钠 作用下， 生成 α,α-dideutero-N-benzoylmethyl-2-iodo-N-methylbenzylamine
  参考文献：
  名称：

  Stereoselective Intermolecular Hydride Shift Mechanism of the New Reduction of Benzylic Alcohols with Acid

  摘要：

  A stereoselective intermolecular hydride shift mechanism of the new reduction reaction of the benzylic hydroxy group of 4-hydroxy-4-phenyl-1,2,3,4-tetrahydroisoquinoline (1) to the corresponding alkane (2) with acid was proved by reaction of the deuterated derivatives (5 and 6) of 1.

  DOI：

  10.3987/com-98-8329

文献信息

• New Reduction Reaction of Benzylic Alcohols with Acid and Proof of the Intermolecular Hydride Shift Mechanism
  作者：Masaru Kihara、Jun-ichi Andoh、Chiaki Yoshida

  DOI：10.3987/com-99-8786

  日期：——

  The new reduction reaction of the hydroxy groups of 4-hydroxy-4-phenyl-1,2,3,4-tetrahydroisoquinolines (1) to the corresponding alkanes (2) with mineral and Lewis acids is reported. A stereoselective intermolecular hydride shift mechanism of the reduction was proved by reaction of the deuterated derivateives (14 and 15) of 1a with 10N HCl-C2H5OH and BBr3 in CH3CN.