(R)-1-tert-butyldiphenylsiloxy-4-(3,4-dichlorophenyl)-1,2-dihydro-naphthalene | 195388-54-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (R)-1-tert-butyldiphenylsiloxy-4-(3,4-dichlorophenyl)-1,2-dihydro-naphthalene
• 英文别名: (R)-4-tert-butyl(4-(3,4-dichlorophenyl)-1,2-dihydronaphthalen-1-yloxy)diphenylsilane；tert-Butyl-[4-(3,4-dichloro-phenyl)-1,2-dihydro-naphthalen-1-yloxy]-diphenyl-silane；tert-butyl-[[(1R)-4-(3,4-dichlorophenyl)-1,2-dihydronaphthalen-1-yl]oxy]-diphenylsilane
• CAS: 195388-54-6
• 化学式: C₃₂H₃₀Cl₂OSi
• 分子量: 529.581
• InChiKey: WMIWRULBHIQPJO-WJOKGBTCSA-N

物化性质

• 沸点：
  584.3±50.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.45
• 重原子数：
  36
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (R)-1-tert-butyldiphenylsiloxy-4-(3,4-dichlorophenyl)-1,2-dihydro-naphthalene 在 palladium on activated charcoal 、 Crabtree's catalyst 二苯基膦叠氮化物 、 四丁基氟化铵 、 氢气 、 potassium carbonate 、 溶剂黄146 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 Lithium-tri-methoxy-alanat 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 乙腈 为溶剂， 20.0 ℃ 、6.89 MPa 条件下， 反应 46.0h， 生成 舍曲林
  参考文献：
  名称：

  Selective functionalization of 1,2-dihydronaphthalenols leads to a concise, stereoselective synthesis of sertraline

  摘要：

  Asymmetric reductive ring opening of oxabenzonorbornadiene provides dihydronaphthalenols in high ee and good yield. Functionality present in this system can be used to elaborate the core towards a number of targets. As an illustration, a concise stereoselective synthesis of the important antidepressant sertraline is described. (C) 1999 Elsevier Science Ltd. Ail rights reserved.

  DOI：

  10.1016/s0040-4020(99)00456-1
• 作为产物：
  描述：

  tert-Butyl-((R)-3,4-dibromo-1,2,3,4-tetrahydro-naphthalen-1-yloxy)-diphenyl-silane 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride sodium hydroxide 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 3.0h， 生成 (R)-1-tert-butyldiphenylsiloxy-4-(3,4-dichlorophenyl)-1,2-dihydro-naphthalene
  参考文献：
  名称：

  Selective functionalization of 1,2-dihydronaphthalenols leads to a concise, stereoselective synthesis of sertraline

  摘要：

  Asymmetric reductive ring opening of oxabenzonorbornadiene provides dihydronaphthalenols in high ee and good yield. Functionality present in this system can be used to elaborate the core towards a number of targets. As an illustration, a concise stereoselective synthesis of the important antidepressant sertraline is described. (C) 1999 Elsevier Science Ltd. Ail rights reserved.

  DOI：

  10.1016/s0040-4020(99)00456-1

文献信息

• Asymmetric Synthesis of Bicyclic Diol Derivatives through Metal and Enzyme Catalysis: Application to the Formal Synthesis of Sertraline
  作者：Patrik Krumlinde、Krisztián Bogár、Jan-E. Bäckvall

  DOI：10.1002/chem.200903114

  日期：2010.4.6

  Enzyme‐ and ruthenium‐catalyzed dynamic kinetic asymmetric transformation (DYKAT) of bicyclic diols to their diacetates was highly enantio‐ and diastereoselective to give the corresponding diacetates in high yield with high enantioselectivity (99.9 % ee). The enantiomerically pure diols are accessible by simple hydrolysis (NaOH, MeOH), but an alternative enzyme‐catalyzed ester cleavage was also used

  酶和钌催化的双环二醇向其双乙酸酯的动态动力学不对称转化（DYKAT）具有很高的对映和非对映选择性，从而以高收率和高对映选择性（99.9％ee）得到相应的双乙酸酯 。对映体纯的二醇可通过简单的水解（NaOH，MeOH）进行水解，但是还使用了另一种酶催化的酯裂解方法，以极高的非对映异构体纯度得到反式二醇（R，R）-1 b（反式/顺式= 99.9：0.1，> 99.9％  ee）。结果表明，在钌催化的Oppenauer型反应中，二醇可以选择性地氧化为酮醇。从简单的外消旋的顺式/反式二醇1b证实了舍曲林的形式对映体选择性合成。
• General Strategy toward the Tetrahydronaphthalene Skeleton. An Expedient Total Synthesis of Sertraline
  作者：Mark Lautens、Tomislav Rovis

  DOI：10.1021/jo971115x

  日期：1997.8.1
• Selective functionalization of 1,2-dihydronaphthalenols leads to a concise, stereoselective synthesis of sertraline
  作者：Mark Lautens、Tomislav Rovis

  DOI：10.1016/s0040-4020(99)00456-1

  日期：1999.7

  Asymmetric reductive ring opening of oxabenzonorbornadiene provides dihydronaphthalenols in high ee and good yield. Functionality present in this system can be used to elaborate the core towards a number of targets. As an illustration, a concise stereoselective synthesis of the important antidepressant sertraline is described. (C) 1999 Elsevier Science Ltd. Ail rights reserved.