(1R,4S)-4-(3,4-dichloro-phenyl)-1,2,3,4-tetrahydro-naphthalen-1-ol | 167026-40-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: (1R,4S)-4-(3,4-dichloro-phenyl)-1,2,3,4-tetrahydro-naphthalen-1-ol
• 英文别名: (1R,4S)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydronaphthalen-1-ol
• CAS: 167026-40-6
• 化学式: C₁₆H₁₄Cl₂O
• 分子量: 293.193
• InChiKey: GZQAUCBRPSENQB-MEDUHNTESA-N

物化性质

• 沸点：
  431.0±45.0 °C(Predicted)
• 密度：
  1.324±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (1R,4S)-4-(3,4-dichloro-phenyl)-1,2,3,4-tetrahydro-naphthalen-1-ol 在 palladium on activated charcoal 二苯基膦叠氮化物 、 氢气 、 potassium carbonate 、 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 、 乙腈 为溶剂， 反应 43.0h， 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：

  (R)-1-tert-butyldiphenylsiloxy-4-(3,4-dichlorophenyl)-1,2-dihydro-naphthalene 在 Crabtree's catalyst 四丁基氟化铵 、 氢气 、 溶剂黄146 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 (1R,4S)-4-(3,4-dichloro-phenyl)-1,2,3,4-tetrahydro-naphthalen-1-ol
  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

• Identification of an Esterase Isolated Using Metagenomic Technology which Displays an Unusual Substrate Scope and its Characterisation as an Enantioselective Biocatalyst
  作者：Declan P. Gavin、Edel J. Murphy、Aoife M. Foley、Ignacio Abreu Castilla、F. Jerry Reen、David F. Woods、Stuart G. Collins、Fergal O'Gara、Anita R. Maguire

  DOI：10.1002/adsc.201801691

  日期：2019.6.6

  Evaluation of an esterase annotated as 26D isolated from a marine metagenomic library is described. Esterase 26D was found to have a unique substrate scope, including synthetic transformations which could not be readily effected in a synthetically useful manner using commercially available enzymes. Esterase 26D was more selective towards substrates which had larger, more sterically demanding substituents

  描述了评估从海洋宏基因组库中分离为26D的酯酶的方法。发现酯酶26D具有独特的底物范围，包括使用市售酶不易以合成有用的方式实现的合成转化。酯酶26D是更具选择性的朝向具有较大的，更空间要求的取代基的底物（即，异-丙基或叔-丁基基团）上的β碳，这是相对于其中显示的偏好基板与空间位先前测试的市售的酶β-碳原子上的取代基（例如甲基）要求较低。
• Chemoenzymatic Synthesis of Sertraline
  作者：Lisa Marx、Nicolás Ríos-Lombardía、Philipp Süss、Matthias Höhne、Francisco Morís、Javier González-Sabín、Per Berglund

  DOI：10.1002/ejoc.201901810

  日期：2020.1.31

  A chemoenzymatic approach has been developed for the preparation of sertraline, an established anti-depressant drug. Ketoreductases (KREDs) were employed to yield a key chiral precursor. The biored ...

  已经开发了一种化学酶促方法来制备舍曲林，一种成熟的抗抑郁药。酮还原酶 (KRED) 用于产生关键的手性前体。生物红...
• Efficient kinetic resolution in hydroboration of 1,2-dihydronaphthalenes
  作者：Kenji Maeda、John M. Brown

  DOI：10.1039/b111175b

  日期：2002.2.12

  1-Substituted 1,2-dihydronaphthalenes undergo kinetic resolution during asymmetric hydroboration with Rh–QUINAP complexes.

  1-取代的1,2-二氢萘在与Rh–QUINAP复合物进行不对称氢硼化过程中发生动力学分离。
• 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
• Asymmetric reduction of substituted indanones and tetralones catalyzed by chiral dendrimer and its application to the synthesis of (+)-sertraline
  作者：Guangyin Wang、Changwu Zheng、Gang Zhao

  DOI：10.1016/j.tetasy.2006.07.010

  日期：2006.8

  A recoverable dendrimeric supported prolinol was used as a catalyst in the asymmetric reduction of indanones and tetralones to give separable cis and trans isomers up to 97% ee. This method was also applied in the enantio selective synthesis of the antidepressant drug (+)-sertraline. (c) 2006 Elsevier Ltd. All rights reserved.