2-[(2-Iodophenyl)methyl-methylamino]-1-phenylethanone | 113258-89-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-[(2-Iodophenyl)methyl-methylamino]-1-phenylethanone
• CAS: 113258-89-2
• 化学式: C₁₆H₁₆INO
• 分子量: 365.214
• InChiKey: KDXXKRDIWCJPRK-UHFFFAOYSA-N

物化性质

• 沸点：
  421.2±30.0 °C(Predicted)
• 密度：
  1.496±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-[(2-Iodophenyl)methyl-methylamino]-1-phenylethanone 在 正丁基锂 、 重水 、 三溴化硼 、 三乙胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 氘代甲醇-d 、 乙腈 为溶剂， 反应 19.5h， 生成
  参考文献：
  名称：

  苯甲醇与酸的新还原反应及分子间氢化物转移机理的证明

  摘要：

  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.

  DOI：

  10.3987/com-99-8786
• 作为产物：
  描述：

  2-溴苯乙酮 、 2-iodo-N-methylbenzylamine 生成 2-[(2-Iodophenyl)methyl-methylamino]-1-phenylethanone
  参考文献：
  名称：

  Kihara Masaru, Kashimoto Minoru, Kobayashi Yoshimaro, Nagao Yoshimitsu, M+, Chem. and Pharm. Bull, 42 (1994) N 1, S 67-73

  摘要：

  DOI：

文献信息

• A convenient synthesis of 4-substituted 1,2,3,4-tetrahydroisoquinolin-4-ols by a novel intramolecular barbier reaction and by an insertion reaction: reaction scope and limitations
  作者：Masaru Kihara、Minoru Kashimoto、Yoshimaro Kobayashi

  DOI：10.1016/s0040-4020(01)80579-2

  日期：1992.1

  4-Substituted 1,2,3,4-tetrahydroisoquinolin-4-ols were prepared from -(2-iodobenzyl)phenacylamines by an intramolecular Barbier reaction with butyllithium and by an insertion reaction with zerovalent nickel. The scope and limitations of these reactions were discussed.

  由-（2-碘苄基）苯甲胺通过与丁基锂的分子内Barbier反应并通过与零价镍的插入反应制备4-取代的1,2,3,4-四氢异喹啉-4-醇。讨论了这些反应的范围和局限性。
• A new intramolecular barbier reaction of N-(2-iodobenzyl)phenacylamines: A convenient synthesis of 1,2,3,4-tetrahydroisoquinomn-4-ols
  作者：Masaru Kihara、Minoru Kashimoto、Yoshimaro Kobayashi、Shigeru Kobayashi

  DOI：10.1016/s0040-4039(00)98068-7

  日期：1990.1

  4-Phenyl-1,2,3,4-tetrahydroisoquinolin-4-ols were prepared by an intramolecular Barbier reaction of N-(2-iodobenzyl)phenacylamines with butyllithium in good yields.

  通过N-（2-碘苄基）苯胺与丁基锂的分子内Barbier反应以良好的收率制备4-苯基-1,2,3,4-四氢异喹啉-4-醇。
• New Entry of Coupling Reaction of Phenacylamine Derivatives with Silylstannane.
  作者：Yasumasa Iwai、Kumiko Kita、Yoko Matsushita、Aiko Yamauchi、Masaru Kihara

  DOI：10.1248/cpb.50.441

  日期：——

  The new coupling reaction of phenacylamines with silylstannane and lithium diisopropylamide (LDA) is reported. The treatment of a phenacylamine iodide 1 with (trimethylsilyl)tributylstannane (Me3SiSnBu3) and cesium fluoride (CsF) gave a dimerization product 2 having no iodine atom. Reaction of 1 with LDA afforded a dimerization product 3 with an iodine atom. The products 2 and 3 were separated to the meso and racemic isomers, respectively.

  报道了苯甲酰胺与甲硅烷基锡烷和二异丙基氨基锂（LDA）的新偶联反应。用(三甲基甲硅烷基)三丁基锡烷(Me 3 SiSnBu 3 )和氟化铯(CsF)处理苯甲酰碘化胺1，得到不含碘原子的二聚产物2。 1与LDA反应得到带有碘原子的二聚产物3。产物2和3分别分离为内消旋异构体和外消旋异构体。
• Stereoselective Intermolecular Hydride Shift Mechanism of the New Reduction of Benzylic Alcohols with Acid
  作者：Masaru Kihara、Junichi Andoh、Chiaki Yoshida

  DOI：10.3987/com-98-8329

  日期：——

  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.
• KIHARA, MASARU;KASHIMOTO, MINORU;KABAYASHI, SHIGERU;ISHIDA, YUKIO;MORITOK+, J. MED. CHEM., 33,(1990) N, C. 2283-2286
  作者：KIHARA, MASARU、KASHIMOTO, MINORU、KABAYASHI, SHIGERU、ISHIDA, YUKIO、MORITOK+

  DOI：——

  日期：——