cis-(1S,2R)-1-(methylamino)-2-indanol | 164347-52-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: cis-(1S,2R)-1-(methylamino)-2-indanol
• 英文别名: (1S,2R)-(+)-cis-1-(N-methyl)aminoindan-2-ol；(1S,2R)-cis-N-methyl-1-amino-2-indanol；(1R,2S)-cis-1-methylamino-2-indanol；N-methyl (1S,2R)-1-amino-2-indanol；N-methyl-(1S,2R)-1-amino-2-indanol；N-methyl-(1S,2R)-cis-1-amino-2-indanol；(1S,2R)-1-(methylamino)-2,3-dihydro-1H-inden-2-ol
• CAS: 164347-52-8
• 化学式: C₁₀H₁₃NO
• 分子量: 163.219
• InChiKey: XRSKXRSFBQMVOK-ZJUUUORDSA-N

物化性质

• 熔点：
  114 °C
• 沸点：
  294.6±40.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  32.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  cis-(1S,2R)-1-(methylamino)-2-indanol 在 sodium hydroxide 、 lithium aluminium tetrahydride 、 四甲基乙二胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 生成 3-Benzyloxymethyl-5-hydroxy-2-phenyl-pentanoic acid ((1S,2R)-2-hydroxy-indan-1-yl)-methyl-amide
  参考文献：
  名称：

  伪麻黄碱作为不对称迈克尔反应的手性助剂：3-芳基-δ-内酯的合成。

  摘要：

  [反应：见正文]报道了伪麻黄碱酰胺的不对称迈克尔反应。1，5-二羰基产物按两步还原/内酯化顺序转化为3-芳基-δ-内酯。该方法提供了对映体富集的反式3，4-二取代的δ-内酯的途径。

  DOI：

  10.1021/ol0259847
• 作为产物：
  描述：

  (1S,2R)-(-)-1-氨基-2-茚醇 在 sodium tetrahydroborate 、 三氟化硼乙醚 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 26.0h， 生成 cis-(1S,2R)-1-(methylamino)-2-indanol
  参考文献：
  名称：

  Practical Asymmetric Synthesis of an Endothelin Receptor Antagonist

  摘要：

  An efficient, practical, asymmetric synthesis of the endothelin receptor antagonist 1 is reported. The key pyridine-fused cyclopentane ring bearing three consecutive chiral centers was constructed by first an auxiliary induced asymmetric conjugate addition of the bottom aryllithium from 19 to an unsaturated ester 21 in high diastereoselectivity. After a highly diastereoselective addition of the top aryl Grignard reagent to the aldehyde 22, the alcohol product then underwent a stereospecific intramolecular alkylation of the ester enolate by the phosphate of the alcohol, resulting in the desired trans-trans relative stereochemistry on the cyclopentane ring. The two key chiral centers that set the chirality of the molecule were both induced from cis-1-amino-2-indanol-derived chiral auxiliaries, one in the conjugate addition reaction, the other in setting the chiral center of the bottom side chain via chiral alkylation of an enolate. Oxidation of the primary alcohol to the carboxylic acid in the bottom side chain was carried out with the newly developed TEMPO/bleach-catalyzed oxidation by sodium chlorite (NaClO2) or chromium oxide catalyzed oxidation by periodic acid. The overall process has been run successfully to make multikilograms of the drug in high purity.

  DOI：

  10.1021/jo991292t

文献信息

• Asymmetric Conjugate Addition of Ketones to β-Nitrostyrenes by Means of 1,2-Amino-Alcohol-Derived Prolinamides as Bifunctional Catalysts
  作者：Diana Almaşi、Diego A. Alonso、Enrique Gómez-Bengoa、Yvonne Nagel、Carmen Nájera

  DOI：10.1002/ejoc.200700031

  日期：2007.5

  This work has been supported by the Direccion General de Investigacion of the Ministerio de Educacion y Ciencia (CTQ2004-00808/BQU), by the Generalitat Valenciana (CTIOIB/2002/320, GRUPOS03/134, GRUPOS05/11 and GV05/157) and the University of Alicante.

  这项工作得到了教育部长和 Ciencia 的 Direccion General de Investigacion (CTQ2004-00808/BQU)、Generalitat Valenciana (CTIOIB/2002/320、GRUPOS03/134、GRUPOS05/11 和 GV05) 和 GV05/阿利坎特大学。
• Chemo‐ and Regioselective Ring Construction Driven by Visible‐Light Photoredox Catalysis: an Access to Fluoroalkylated Oxazolidines Featuring an All‐Substituted Carbon Stereocenter
  作者：Xue‐Qiang Chu、Danhua Ge、Mao‐Lin Wang、Weidong Rao、Teck‐Peng Loh、Zhi‐Liang Shen

  DOI：10.1002/adsc.201900585

  日期：2019.9.3

  ether, fluoroalkyl halide, and chiral amino alcohol in a single reaction vessel, which provides an efficient strategy for expanding the pool of pharmaceutically important heterocycles featuring an all‐substituted carbon stereocenter. This process proceeds efficiently in a chemo‐, regio‐, and stereoselective fashion under mild reaction conditions at room temperature and exhibits broad functional group

  通过在有机分子中掺入全取代碳立构中心而赋予的独特优势已得到广泛认可。在这项工作中，我们描述了访问C的三部分环化通过在一个反应​​容器中将易得的甲硅烷基烯醇醚，氟代烷基卤化物和手性氨基醇进行片段组装而得到‐2氟代烷基化的恶唑烷，这为扩展具有全取代碳立构中心的药学重要杂环库提供了有效策略。在室温下，在温和的反应条件下，该过程以化学，区域和立体选择性方式有效地进行，并表现出广泛的官能团耐受性。该受控异环序列的成功实现取决于通过可见光光氧化还原催化的独特的全氟烷基化，区域和立体选择性自由基环化。此外，还实现了直接使用酮作为底物的单锅法。
• Practical Asymmetric Synthesis of a Selective Endothelin A Receptor (ETA) Antagonist
  作者：Zhiguo J. Song、Matthew Zhao、Lisa Frey、Jing Li、Lushi Tan、Cheng Y. Chen、David M. Tschaen、Richard Tillyer、Edward J. J. Grabowski、Ralph Volante、Paul J. Reider、Yoshiaki Kato、Shigemitsu Okada、Takayuki Nemoto、Hiroki Sato、Atsushi Akao、Toshiaki Mase

  DOI：10.1021/ol016601s

  日期：2001.10.1

  [structure: see text]. A practical, chromotography-free asymmetric synthesis was developed for the large scale preparation of an endothelin receptor antagonist 2. This synthesis includes a new efficient process for the preparation of 6-bromo-2,3-dihydrobenzofuran, a stereoselective conjugate addition of an aryllithium followed by stereospecific addition of the Grignard reagent of the top aryl bromide

  [结构：见文字]。开发了一种实用的无色谱不对称合成方法，用于大规模制备内皮素受体拮抗剂2。该合成方法包括制备6-溴-2,3-二氢苯并呋喃的新有效方法，即芳基锂的立体选择性共轭加成。其次是立体定向添加顶部芳基溴的格氏试剂，以及氨基磷酸介导的立体定向分子内烯醇酸酯烷基化，这导致形成带有三个连续不对称中心的五元环。
• [EN] DPP-IV INHIBITORS<br/>[FR] INHIBITEURS DE LA DPP-IV
  申请人：GRAFFINITY PHARMACEUTICALS AG

  公开号：WO2005095343A1

  公开（公告）日：2005-10-13

  The invention relates to compounds of formula (I), Z-C(R<1>R<2>)-C(R<3>NH2)-C(R<4>R<5>)-X-N(R<6>R<7>), wherein Z, R<1-7> and X have the meaning as cited in the description and the claims. Said compounds are useful as DPP-lV inhibitors. The invention also relates to the preparation of such compounds as well as the production and use thereof as medicament.

  该发明涉及式(I)的化合物，其中Z-C(R1R2)-C(R3NH2)-C(R4R5)-X-N(R6R7)，其中Z，R1-7和X的含义如描述和权利要求中所述。所述化合物可用作DPP-IV抑制剂。该发明还涉及制备此类化合物以及其作为药物的生产和使用。
• Asymmetric transfer hydrogenation of ketones using amino alcohol and monotosylated diamine derivatives of indane
  作者：Matthew J. Palmer、Jennifer A. Kenny、Tim Walsgrove、Aparecida M. Kawamoto、Martin Wills

  DOI：10.1039/b108538g

  日期：2002.1.23

  A series of 1,2-amino alcohol and 1,2-monotosylated diamine derivatives of indane have been applied as ligands in the asymmetric ruthenium(II)-catalysed transfer hydrogenation reaction of a series of ketones. Of these, the cis-1-aminoindan-2-ol derivative gives some of the highest asymmetric inductions reported for any amino alcohol ligand in this application.

  一系列1,2-氨基醇和1,2-单磺酰化二胺茚衍生物已被应用于不对称钌(II)催化的酮类转移氢化反应中作为配体。其中，顺-1-氨基茚-2-醇衍生物在此应用中展现出一些报道中最高的不对称诱导效果，相较于其他氨基醇配体。