(S)-tert-butyl (1,2-dihydronaphthalen-1-yl)carbamate | 1446434-26-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (S)-tert-butyl (1,2-dihydronaphthalen-1-yl)carbamate
• 英文别名: tert-butyl N-[(1S)-1,2-dihydronaphthalen-1-yl]carbamate
• CAS: 1446434-26-9
• 化学式: C₁₅H₁₉NO₂
• 分子量: 245.321
• InChiKey: KEGJJWQYLUIEEI-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 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 (1,2-dihydronaphthalen-1-yl)carbamate 在 溴 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 12.33h， 生成 tert-butyl N-[(1S)-4-bromo-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
• 作为产物：
  描述：

  (R_s)-N-[(S)-1,2-dihydronaphthalen-1-yl]-2-methylpropane-2-sulfinamide 在 盐酸 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 0.33h， 生成 (S)-tert-butyl (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

• Palladium/Lewis Acid Cocatalyzed Reductive Asymmetric Ring-Opening Reaction of Azabenzonorbornadienes with Tertiary Amines as the Hydrogen Source
  作者：Dapeng Zhang、Ruhima Khan、Fan Yang、Xuexin Zhang、Guoli Shen、Yang Gao、Ruifeng Fan、Weiqing Sun、Baomin Fan

  DOI：10.1002/ejoc.201800503

  日期：2018.7.13

  Palladium and silver cocatalyzed the asymmetric transfer hydrogenation of azabenzonorbornadienes with tertiary amines to give the corresponding ring‐opening products in high yields with good to excellent enantioselectivities. (R)‐2,2′‐Bis(diphenylphosphino)‐1,1′‐binaphthyl [(R)‐BINAP] and para‐methoxybenzoic acid were used as the chiral ligand and additive, respectively, in the reported protocol.

  钯和银共催化氮杂苯并降冰片二烯与叔胺的不对称转移加氢，从而以高收率和良好或优异的对映选择性提供相应的开环产物。（R）-2,2'-双（二苯基膦基）-1,1'-联萘[[ R）-BINAP]和对-甲氧基苯甲酸分别用作所报告的方案中的手性配体和添加剂。
• Asymmetric Transfer Hydrogenation of Heterobicyclic Alkenes with Water as Hydrogen Source
  作者：Guoli Shen、Jingchao Chen、Dandan Xu、Xia Zhang、Yongyun Zhou、Baomin Fan

  DOI：10.1021/acs.orglett.9b00059

  日期：2019.3.1

  The asymmetric transfer hydrogenation of heterobicyclic alkenes was accomplished by using water as the sole hydrogen source. The transformation was co-catalyzed by Pd(OAc)2/Zn(OTf)2 dual catalyst with metallic zinc as reducing agent. Various azabenzonorbornadienes and oxabenzonorbornadienes were transformed to the corresponding chiral 1,2-dihydronaphthalenes by the asymmetric reductive ring-opening

  杂双环烯烃的不对称转移氢化是通过使用水作为唯一的氢源来完成的。Pd（OAc）2 / Zn（OTf）2双重催化剂与金属锌作为还原剂共同催化转化。通过不对称的还原性开环反应，各种氮杂苯并降冰片二烯和氧杂苯并降冰片二烯被转化为相应的手性1,2-二氢萘，具有良好的至优异的对映选择性。
• Asymmetric Hydrophosphination of Heterobicyclic Alkenes: Facile Access to Phosphine Ligands for Asymmetric Catalysis
  作者：Zhiwu Lu、Haoyang Zhang、Zhiping Yang、Ning Ding、Ling Meng、Jun Wang

  DOI：10.1021/acscatal.8b04787

  日期：2019.2.1

  Asymmetric hydrophosphination is the most atomically economical and straightforward approach to the construction of chiral organophosphorus compounds. Good stereoselectivities have been achieved in asymmetric hydrophosphination of an electron-deficient C═C double bond, but substrates involving nonpolar C═C bonds remain difficult and are rarely tackled. Herein, we report asymmetric hydrophosphination

  不对称氢磷酸化是手性有机磷化合物构建中最原子经济且最直接的方法。在缺乏电子的C═C双键的不对称加氢磷化反应中已经获得了良好的立体选择性，但是涉及非极性C═C键的底物仍然很困难，而且很少解决。在本文中，我们报道了非电子活化的双键的非对称氢磷酸化，其立体控制程度非常高。该策略为制备高产率（高达99％的产率）和对映选择性（高达ee的99％）的叔膦提供了一个方便且广泛适用的平台。
• Palladium/Lewis Acid Co-catalyzed Divergent Asymmetric Ring-Opening Reactions of Azabenzonorbornadienes with Alcohols
  作者：Fan Yang、Jingchao Chen、Jianbin Xu、Fujie Ma、Yongyun Zhou、Madhuri Vikas Shinde、Baomin Fan

  DOI：10.1021/acs.orglett.6b02300

  日期：2016.10.7

  catalysts and Lewis acids, both the additional and reductive asymmetric ring-opening reactions of azabenzonorbornadienes with alcohols were accomplished with good chemoselectivity, regioselectivity, and enantioselectivity. It was proven that the reductive ring-opening products were generated through a transfer-hydrogenation process with alcohols as hydrogen source.

  通过微调手性钯催化剂和路易斯酸的组合，氮杂苯并降冰片二烯与醇的附加和还原性不对称开环反应均具有良好的化学选择性，区域选择性和对映选择性。事实证明，还原性开环产物是通过以醇为氢源的转移加氢过程产生的。