(+)-(S)-5-Methoxy-1-tetralol | 182497-75-2

• 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-Methoxy-1-tetralol
• 英文别名: (S)-(+)-5-methoxy-1,2,3,4-tetrahydronaphthalen-1-ol；(S)-1,2,3,4-tetrahydro-5-methoxy-1-naphthalenol；(S)-1,2,3,4-tetrahydro-5-methoxynaphthalen-1-ol；(1S)-5-Methoxy-1,2,3,4-tetrahydronaphthalen-1-OL
• CAS: 182497-75-2
• 化学式: C₁₁H₁₄O₂
• 分子量: 178.231
• InChiKey: KEHUANDJKBFXBA-JTQLQIEISA-N

物化性质

• 熔点：
  97.8-98.2 °C(Solv: toluene (108-88-3); hexane (110-54-3))
• 沸点：
  324.4±37.0 °C(Predicted)
• 密度：
  1.133±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (+)-(S)-5-Methoxy-1-tetralol 在 palladium on activated charcoal sodium tetrahydroborate 、 叠氮磷酸二苯酯 、 氢气 、 三溴化硼 、 对甲苯磺酸 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 生成
  参考文献：
  名称：

  Discovery of new diphenyloxazole derivatives containing a pyrrolidine ring: Orally active prostacyclin mimetics. Part 2

  摘要：

  Synthetic and biological evaluation of novel diphenyloxazole derivatives containing a pyrrolidine ring, as a prostacyclin mimetic without the PG skeleton, are described. Asymmetric reduction of a ketone using a chiral Ru complex and reductive amination by NaBH4 produces four isomers of the tetrahydronaphthalene ring and the pyrrolidine ring with high stereoselectivity. FR193262 (4), (R,R)-diphenyloxazolyl pyrrolidine derivative, displays high potency and agonist efficacy at the IP receptor and has good bioavailability in rats and dogs. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.04.042
• 作为产物：
  描述：

  5-甲氧基-3,4-二氢-2H-1-萘酮 在 [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂ 、 sodium formate 作用下， 以 水 、 异丙醇 为溶剂， 反应 5.0h， 以91.5%的产率得到
  参考文献：
  名称：

  以壳聚糖为手性源的水介质中钌催化的机械化学不对称转移氢化

  摘要：

  随着对可持续方法需求的增加，合成化学正专注于应用对环境无害的方法，例如由替代能源传输引起的快速反应。壳聚糖是一种天然来源的手性生物聚合物，可用于不对称催化。Ru-壳聚糖复合物的应用以及机械化学活化可能为光学纯醇的可持续制备提供巨大的机会。在本研究中，我们优化了在混合磨中进行的 4-色满酮的机械化学不对称转移氢化。该反应由原位催化形成Ru-壳聚糖复合物，在水性介质中应用HCOONa作为氢供体。我们检查了不同研磨介质尺寸的机械效应，然后使用 24 种前手性酮探索了系统的范围，范围从杂环酮和碳环酮到苯乙酮衍生物。在大多数情况下，反应成功放大至 1 mmol，产物以良好的收率和出色的对映选择性分离。我们目前的研究是朝着开发环境友好和可持续的对映选择性过程迈出的重要一步，因为替代活化方法在水性介质中使用可生物降解的手性源提供了光学富集的醇。

  DOI：

  10.1016/j.mcat.2022.112162

文献信息

• Cobalt-catalyzed Oxidative Kinetic Resolution of Secondary Benzylic Alcohols with Molecular Oxygen
  作者：Tohru Yamada、Sho Higano、Takanori Yano、Yoshihiro Yamashita

  DOI：10.1246/cl.2009.40

  日期：2009.1.5

  The oxidative kinetic resolution of secondary alcohols using molecular oxygen and olefins was catalyzed by the optically active ketoiminatocobalt(II) complexes. The various secondary benzylic alcoh...

  使用分子氧和烯烃的仲醇的氧化动力学拆分由光学活性的酮亚氨基钴 (II) 配合物催化。各种二级苯甲醇...
• Enantioselective Reduction of Ketones and Imines Catalyzed by (CN-Box)ReV-Oxo Complexes
  作者：Kristine A. Nolin、Richard W. Ahn、Yusuke Kobayashi、Joshua J. Kennedy-Smith、F. Dean Toste

  DOI：10.1002/chem.201001164

  日期：2010.8.16

  application of chiral, non‐racemic ReV–oxo complexes to the enantioselective reduction of prochiral ketones is described. In addition to the enantioselective reduction of prochiral ketones, we report the application of these complexes to 1) a tandem Meyer–Schuster rearrangement/reduction to access enantioenriched allylic alcohols and 2) the enantioselective reduction of imines.

  描述了手性非外消旋 Re V - oxo 配合物在前手性酮的对映选择性还原中的开发和应用。除了前手性酮的对映选择性还原外，我们还报告了这些复合物在以下方面的应用：1）串联 Meyer-Schuster 重排/还原以获取对映体富集的烯丙醇和 2）亚胺的对映选择性还原。
• Homogeneous Enantioselective Catalysis in a Continuous-Flow Microreactor: Highly Enantioselective Borohydride Reduction of Ketones Catalyzed by Optically Active Cobalt Complexes
  作者：Takuo Hayashi、Satoshi Kikuchi、Yukako Asano、Yoshishige Endo、Tohru Yamada

  DOI：10.1021/op300061k

  日期：2012.6.15

  Highly enantioselective homogeneous catalysis under continuous-flow conditions was established for the cobalt-catalyzed borohydride reduction of tetralone derivatives. A microreactor allowed higher reaction temperature with the residence time of 12 min than the corresponding batch system to maintain enantioselectivity as well as reactivity. The present system was directly applied to gram-scale synthesis

  建立了在连续流动条件下的高对映选择性均相催化剂，用于钴催化硼氢化物还原四氢萘酮衍生物。与相应的间歇系统相比，微反应器允许更高的反应温度和12分钟的停留时间，以保持对映选择性和反应性。本系统直接用于克级合成，以提供具有92％ee的还原产物。
• Penicillamine as a ligand in the catalytic asymmetric reduction of ketones
  作者：Stephen Hanessian、Eric Jnoff、Andrew M Griffin

  DOI：10.1139/v01-174

  日期：2002.8.1

  Amino acids derived from D-penicillamine and thiazolidines were studied as ligands for the catalytic asymmetric reduction of ketones with borane. Enantioselectivities up to 83% ee were observed.Key words: asymmetric reduction, penicillamine, thiazolidine, amino acid.

  从D-青霉胺和噻唑啉衍生的氨基酸被研究作为硼烷催化不对称还原酮的配体。观察到高达83% ee的对映选择性。关键词：不对称还原，青霉胺，噻唑啉，氨基酸。
• 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.