(cis)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthol

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: (cis)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthol
• 英文别名: (1R,4R)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydronaphthalen-1-ol
• 化学式: C₁₆H₁₄Cl₂O
• 分子量: 293.193
• InChiKey: GZQAUCBRPSENQB-BDJLRTHQSA-N

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

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  ——	(1R,4S)-4-(3,4-dichloro-phenyl)-1,2,3,4-tetrahydro-naphthalen-1-ol	167026-40-6	C16H14Cl2O	293.193
  4-(3,4-二氯苯基)-1-四氢萘酮	4-(3,4-dichlorophenyl)-1-tetralone	79560-19-3	C16H12Cl2O	291.177
  4-(3,4-二氯苯)-3,4-二氢-2H-萘-1-酮	(4S)-4-(3,4-dichlorophenyl)-1-tetralone	124379-29-9	C16H12Cl2O	291.177
  (+)-(1R)-4-(3,4-二氯苯基)-1,2-二氢萘-1-醇	(R)-4-(3,4-dichlorophenyl)-1,2-dihydro-naphthalen-1-ol	195388-55-7	C16H12Cl2O	291.177

反应信息

• 作为反应物：
  描述：

  (cis)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthol 、 乙酸酐 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以56%的产率得到cis-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthalenyl acetate
  参考文献：
  名称：

  使用超基因组技术分离的酯酶的鉴定，该酶显示出异常的底物范围，并表征为对映选择性生物催化剂

  摘要：

  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。

  DOI：

  10.1002/adsc.201801691
• 作为产物：
  描述：

  (R)-1-tert-butyldiphenylsiloxy-4-(3,4-dichlorophenyl)-1,2-dihydro-naphthalene 在 manganese(IV) oxide 、 sodium tetrahydroborate 、 Crabtree catalyst 、 四丁基氟化铵 、 氢气 、 溶剂黄146 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 氯仿 为溶剂， 反应 72.0h， 生成 (cis)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthol
  参考文献：
  名称：

  General Strategy toward the Tetrahydronaphthalene Skeleton. An Expedient Total Synthesis of Sertraline

  摘要：

  DOI：

  10.1021/jo971115x

文献信息

• 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...
• AN OMEGA-TRANSAMINASE ENZYME
  申请人：University College Cork-National University of Ireland, Cork

  公开号：EP3604507A1

  公开（公告）日：2020-02-05

  An isolated ω-transaminase enzyme comprising an amino acid sequence of SEQUENCE ID NO: 1, or encoded by a nucleic acid sequence of SEQUENCE ID NO: 2, is provided and is derived from the marine sponge Pseudovibrio sp. Also provided are functional variants of the ω-transaminase enzyme that are isolated, have at least 70% sequence identity with SEQUENC ID NO: 1, and are capable of enantioselectively resolving a racemic amine by transformation to a ketone by oxidative deamination, or enantioselectively resolving a racemic ketone by transformation to an amine by reductive amination, in which the amine and ketone typically contain a stereocentre removed from the reacting site. In one embodiment, the functional variant is capable of enantioselectively transforming a (4S)-tetralone intermediate in the synthesis of sertraline, in which the functional variant displays remote stereospecificity for the tetralone intermediate.

  本发明提供了一种分离的ω-转氨酶，该酶包含 SEQUENCE ID NO: 1 的氨基酸序列，或由 SEQUENCE ID NO: 2 的核酸序列编码，其来源于海洋海绵假弧菌（Pseudovibrio sp.还提供了ω-转氨酶的功能变体，这些变体是分离出来的，与 SEQUENC ID NO: 1 至少有 70% 的序列同一性，并且能够通过氧化脱氨转化为酮而对映选择性地解析外消旋胺，或通过还原胺化转化为胺而对映选择性地解析外消旋酮，其中胺和酮通常含有一个从反应位点移除的立体中心。在一个实施方案中，该功能变体能够在合成舍曲林的过程中对映选择性地转化(4S)-四氢萘酮中间体，其中该功能变体对四氢萘酮中间体具有远程立体特异性。
• 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.
• [EN] AN OMEGA-TRANSAMINASE ENZYME<br/>[FR] ENZYME OMÉGA-TRANSAMINASE
  申请人：UNIV COLLEGE CORK NATIONAL UNIV OF IRELAND CORK

  公开号：WO2020025646A1

  公开（公告）日：2020-02-06

  An isolated w-transaminase enzyme comprising an amino acid sequence of SEQUENCE ID NO: 1, or encoded by a nucleic acid sequence of SEQUENCE ID NO: 2, is provided which is derived from marine sponge Pseudovibrio sp.. Also provided are functional variants of the w-transaminase enzyme that are isolated, have at least 80% sequence identity with SEQUENCE ID NO: 1, and are capable of enantioselectively resolving a racemic amine by transformation to a ketone by oxidative deamination, or enantioselectively resolving a racemic ketone by transformation to an amine by reductive amination, in which the amine and ketone typically contain a stereocentre removed from the reacting site. An example of a functional variant is SEQUENCE ID NO:3. In one embodiment, the functional variant is capable of enantioselectively transforming a (4S) -tetralone intermediate in the synthesis of sertraline, in which the functional variant displays remote stereospecificity for the tetralone intermediate.
• 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