(S)-tert-butyl (4-(3,4-dichlorophenyl)-1,2-dihydronaphthalen-1-yl)carbamate | 1446434-30-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (S)-tert-butyl (4-(3,4-dichlorophenyl)-1,2-dihydronaphthalen-1-yl)carbamate
• 英文别名: tert-butyl N-[(1S)-4-(3,4-dichlorophenyl)-1,2-dihydronaphthalen-1-yl]carbamate
• CAS: 1446434-30-5
• 化学式: C₂₁H₂₁Cl₂NO₂
• 分子量: 390.309
• InChiKey: GMZATGKXBUBTPN-IBGZPJMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-tert-butyl (4-(3,4-dichlorophenyl)-1,2-dihydronaphthalen-1-yl)carbamate 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙醇 为溶剂， 以33.333%的产率得到
  参考文献：
  名称：

  Asymmetric Allylation/Ring Closing Metathesis: One-Pot Synthesis of Benzo-fused Cyclic Homoallylic Amines. Application to the Formal Synthesis of Sertraline Derivatives

  摘要：

  A one-pot asymmetric allylation/ring closing metathesis (RCM) sequence for the synthesis of cyclic homoallylic amines has been developed. A library of six- and seven-membered benzo-fused products has been synthesized in good yields and complete diastereoselectivity. The new methodology has been applied to the formal syntheses of the antidepressant Sertraline and the epimeric Norsertraline. The methodology is amenable for the synthesis of analogs.

  DOI：

  10.1021/ol4017113
• 作为产物：
  描述：

  (R_s)-N-[(S)-1,2-dihydronaphthalen-1-yl]-2-methylpropane-2-sulfinamide 在 盐酸 、 potassium carbonate 、 caesium carbonate 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 、 2-(二叔丁基膦)联苯 作用下， 以 1,4-二氧六环 、 甲醇 、 水 、 甲苯 为溶剂， 反应 4.33h， 生成 (S)-tert-butyl (4-(3,4-dichlorophenyl)-1,2-dihydronaphthalen-1-yl)carbamate
  参考文献：
  名称：

  Asymmetric Allylation/Ring Closing Metathesis: One-Pot Synthesis of Benzo-fused Cyclic Homoallylic Amines. Application to the Formal Synthesis of Sertraline Derivatives

  摘要：

  A one-pot asymmetric allylation/ring closing metathesis (RCM) sequence for the synthesis of cyclic homoallylic amines has been developed. A library of six- and seven-membered benzo-fused products has been synthesized in good yields and complete diastereoselectivity. The new methodology has been applied to the formal syntheses of the antidepressant Sertraline and the epimeric Norsertraline. The methodology is amenable for the synthesis of analogs.

  DOI：

  10.1021/ol4017113

文献信息

• Asymmetric Allylation/Ring Closing Metathesis: One-Pot Synthesis of Benzo-fused Cyclic Homoallylic Amines. Application to the Formal Synthesis of Sertraline Derivatives
  作者：Santos Fustero、Rubén Lázaro、Lidia Herrera、Elsa Rodríguez、Natalia Mateu、Pablo Barrio

  DOI：10.1021/ol4017113

  日期：2013.7.19

  A one-pot asymmetric allylation/ring closing metathesis (RCM) sequence for the synthesis of cyclic homoallylic amines has been developed. A library of six- and seven-membered benzo-fused products has been synthesized in good yields and complete diastereoselectivity. The new methodology has been applied to the formal syntheses of the antidepressant Sertraline and the epimeric Norsertraline. The methodology is amenable for the synthesis of analogs.