(+)-(S)-5,7-Dimethyl-1-tetralol | 201684-10-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: (+)-(S)-5,7-Dimethyl-1-tetralol
• 英文别名: (S)-1,2,3,4-tetrahydro-5,7-dimethylnaphthalen-1-ol；5,7-dimethyl-1,2,3,4-tetrahydronaphthalen-1-ol；(S)-5,7-dimethyl-1-tetralol；(1S)-5,7-dimethyl-1,2,3,4-tetrahydronaphthalen-1-ol
• CAS: 201684-10-8
• 化学式: C₁₂H₁₆O
• 分子量: 176.258
• InChiKey: RIRIMDYRPXOLHI-LBPRGKRZSA-N

物化性质

• 熔点：
  87.4-88.0 °C(Solv: dichloromethane (75-09-2); hexane (110-54-3))
• 沸点：
  307.3±11.0 °C(Predicted)
• 密度：
  1.063±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  乙酸酐 、 (+)-(S)-5,7-Dimethyl-1-tetralol 在 4-二甲氨基吡啶 、 三乙胺 作用下， 反应 1.0h， 生成 (S)-1,2,3,4-tetrahydro-5,7-dimethylnaphthalen-1-yl acetate
  参考文献：
  名称：

  Enzymatic resolution of α-tetralols by CALB-catalyzed acetylation

  摘要：

  A series of homochiral alpha-tetralols, as well as their respective acetates, has been obtained by esterification of racemic tetralols, using Candida antarctica lipase (CALB-Novozym(R) 435) as the biocatalyst. This enzyme is shown to be highly efficient for the kinetic resolution of the substrates studied, affording the (+)-tetralols and the (+)-acetates in excellent enantiomeric excess (up to >99%) and very good yields (>40%). (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.05.007
• 作为产物：
  描述：

  5,7-二甲基-1-萘满酮 在 Candida antarctica lipase B 、 sodium tetrahydroborate 作用下， 以 甲醇 、 正己烷 为溶剂， 反应 22.0h， 生成 (+)-(S)-5,7-Dimethyl-1-tetralol
  参考文献：
  名称：

  Enzymatic resolution of α-tetralols by CALB-catalyzed acetylation

  摘要：

  A series of homochiral alpha-tetralols, as well as their respective acetates, has been obtained by esterification of racemic tetralols, using Candida antarctica lipase (CALB-Novozym(R) 435) as the biocatalyst. This enzyme is shown to be highly efficient for the kinetic resolution of the substrates studied, affording the (+)-tetralols and the (+)-acetates in excellent enantiomeric excess (up to >99%) and very good yields (>40%). (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.05.007

文献信息

• Design of Ru(II)-NHC-Diamine Precatalysts Directed by Ligand Cooperation: Applications and Mechanistic Investigations for Asymmetric Hydrogenation
  作者：Wei Li、Tobias Wagener、Lars Hellmann、Constantin G. Daniliuc、Christian Mück-Lichtenfeld、Johannes Neugebauer、Frank Glorius

  DOI：10.1021/jacs.0c00985

  日期：2020.4.15

  A modular synthesis of Ru(II)-NHC-diamine complexes from readily available chiral N-heterocyclic carbenes (NHCs) and chiral diamines is disclosed for the first time. The well-defined Ru(II)-NHC-diamine complexes show unique structure and coordination chemistry including an unusual tridentate coordination effect of 1,2-diphenylethylenediamine. The isolated air- and moisture-stable Ru(II)-NHC-diamine

  首次公开了从容易获得的手性 N-杂环卡宾 (NHC) 和手性二胺中模块化合成 Ru(II)-NHC-二胺配合物。明确定义的 Ru(II)-NHC-二胺配合物显示出独特的结构和配位化学，包括 1,2-二苯基乙二胺的不寻常的三齿配位效应。分离出的空气和水分稳定的 Ru(II)-NHC-二胺配合物可作为异香豆素、苯并噻吩 1,1-二氧化物和酮的不对称氢化的通用预催化剂。此外，在化学计量反应和核磁共振实验鉴定反应中间体的基础上，结合DFT计算，提出了可能的催化循环。
• Stereochemical Sensitivity of the Human UDP-glucuronosyltransferases 2B7 and 2B17
  作者：Ingo Bichlmaier、Antti Siiskonen、Moshe Finel、Jari Yli-Kauhaluoma

  DOI：10.1021/jm051142c

  日期：2006.3.1

  A set of 28 enantiomers comprising rigid and flexible secondary alcohols was synthesized by the asymmetric Corey-Bakshi-Shibata reduction. The enantiomerically pure alcohols were subjected to enzymatic glucuronidation assays employing the human UDP-glucuronosyltransferases (UGTs) 2B7 and 2BI7. Both UGTs displayed high levels of stereo selectivity, favoring the conjugation of the (R)-enantiomers over their respective (S)-stereoisomers at eudismic ratios up to 256. The spatial arrangement of the hydroxy group determined the diastereoselectivity of the UGT2B17-catalyzed reaction in agreement with Pfeiffer's rule (eudismic activity quotient = 0.83 +/- 0.14). Inhibition studies revealed that the enantiomers had similar affinities toward the enzymes. The diastereoselectivity of the UGT-catalyzed conjugation stemmed, therefore, from the arrangement of the substrates in the catalytic site, rather than from distinct affinities toward the enzymes. Taken together, this study showed that metabolic enzymes that are generally conceived to be rather "flexible" in nature are capable of displaying high levels of chiral distinction.
• BINAP/1,4-Diamine−Ruthenium(II) Complexes for Efficient Asymmetric Hydrogenation of 1-Tetralones and Analogues
  作者：Takeshi Ohkuma、Tomonori Hattori、Hirohito Ooka、Tsutomu Inoue、Ryoji Noyori

  DOI：10.1021/ol049157c

  日期：2004.8.1

  A combined system of a RuCl2(binap)(1,4-diamine) complex and t-C4H9OK in i-C3H7OH catalyzes enantioselective hydrogenation of various 1-tetralone derivatives and some methylated 2-cyclohexenones. Hydrogenation of 2-methyl-1-tetralone under dynamic kinetic resolution gives the cis alcohol with high ee.
• Enzymatic resolution of α-tetralols by CALB-catalyzed acetylation
  作者：Helena M.C. Ferraz、Graziela G. Bianco、Carla C. Teixeira、Leandro H. Andrade、André L.M. Porto

  DOI：10.1016/j.tetasy.2007.05.007

  日期：2007.5

  A series of homochiral alpha-tetralols, as well as their respective acetates, has been obtained by esterification of racemic tetralols, using Candida antarctica lipase (CALB-Novozym(R) 435) as the biocatalyst. This enzyme is shown to be highly efficient for the kinetic resolution of the substrates studied, affording the (+)-tetralols and the (+)-acetates in excellent enantiomeric excess (up to >99%) and very good yields (>40%). (C) 2007 Elsevier Ltd. All rights reserved.