(R)-6-methyl-2,3-dihydro-1H-inden-1-ol | 200425-64-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: (R)-6-methyl-2,3-dihydro-1H-inden-1-ol
• 英文别名: (-)-(R)-6-Methyl-1-indalol；(+/-)-(R)-6-Methyl-1-indalol；(1R)-6-methyl-2,3-dihydro-1H-inden-1-ol
• CAS: 200425-64-5
• 化学式: C₁₀H₁₂O
• 分子量: 148.205
• InChiKey: ATIMDIDJGWMTDD-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  6-甲基-1-茚酮 在 sodium tetrahydroborate 、 Pseudomonas cepacia lipase 、 sodium carbonate 作用下， 以 四氢呋喃 、 甲基叔丁基醚 、 水 为溶剂， 反应 24.0h， 生成 (R)-6-methyl-2,3-dihydro-1H-inden-1-ol
  参考文献：
  名称：

  通过脂肪酶催化衣康酸酐的区​​域和对映选择性开环获得有价值的结构单元

  摘要：

  在此，我们首次报道了由洋葱假单胞菌脂肪酶 ( PCL )催化的生物基衣康酸酐的高度区域和对映选择性开环。-丁基甲基醚 (TBME) 在室温下。该方法简单、高效、环保，可以一步完成一系列高价值的衣康酸单酯（非手性或对映体富集），使用各种醇作为亲核试剂，原子经济性为 100%。在所有情况下，β-单酯异构体都是反应的主要产物。使用非手性伯醇作为底物，以中等至优异的产率（50-90%）获得了多种新型衣康酸酯。对于选定的示例，除了标准技术外，还使用 ​​X 射线衍射进行了产品表征。该方法的应用是通过酶动力学拆分制备对映体富集的 4-单酯衣康酸酯。

  DOI：

  10.1039/d2ob00047d

文献信息

• Lutidine‐Based Chiral Pincer Manganese Catalysts for Enantioselective Hydrogenation of Ketones
  作者：Linli Zhang、Yitian Tang、Zhaobin Han、Kuiling Ding

  DOI：10.1002/anie.201814751

  日期：2019.4

  activities (up to 9800 TON; TON=turnover number), broad substrate scope (81 examples), good functional‐group tolerance, and excellent enantioselectivities (85–98 % ee) in the hydrogenation of various ketones. These aspects are rare in earth‐abundant metal catalyzed hydrogenations. The utility of the protocol have been demonstrated in the asymmetric synthesis of a variety of key intermediates for chiral drugs

  已经开发了一系列含有基于核苷的手性钳式配体的Mn I配合物，这些配合物具有模块化和可调的结构。该配合物在各种酮的氢化反应中显示出前所未有的高活性（高达9800 TON； TON =周转数），广泛的底物范围（81个实例），良好的官能团耐受性和出色的对映选择性（85-98％ee）。这些方面在稀土金属催化的氢化反应中很少见。该协议的实用性已在手性药物的多种关键中间体的不对称合成中得到证明。初步的机理研究表明，底物与催化剂相互作用的外层模式可能主导了催化作用。
• Silylative Kinetic Resolution of Racemic 1-Indanol Derivatives Catalyzed by Chiral Guanidine
  作者：Shuhei Yoshimatsu、Akira Yamada、Kenya Nakata

  DOI：10.1021/acs.joc.7b02493

  日期：2018.1.5

  Efficient kinetic resolution of racemic 1-indanol derivatives was achieved using triphenylchlorosilane by asymmetric silylation in the presence of chiral guanidine catalysts. The chiral guanidine catalyst (R,R)-N-(1-(β-naphthyl)ethyl)benzoguanidine was found to be highly efficient as only 0.5 mol % catalyst loading was sufficient to catalyze the reaction of various substrates with appropriate conversion

  使用三苯基氯硅烷通过在手性胍催化剂存在下的不对称甲硅烷基化反应，可以实现外消旋1-茚满醇衍生物的高效动力学拆分。发现手性胍催化剂（R，R）-N-（1-（β-萘基）乙基）苯并胍是高效的，因为仅0.5mol％的催化剂负载量足以以适当的转化率和高的催化率来催化各种底物的反应。s值（最多89个）。该催化剂体系已成功应用于具有高选择性的外消旋1-茚满醇的克级甲硅烷基化动力学拆分。
• HYDROXY-SUBSTITUTED OREXIN RECEPTOR ANTAGONISTS
  申请人：MERCK SHARP & DOHME CORP.

  公开号：US20160068510A1

  公开（公告）日：2016-03-10

  The present invention is directed to hydroxy compounds which are antagonists of orexin receptors. The present invention is also directed to uses of the compounds described herein in the potential treatment or prevention of neurological and psychiatric disorders and diseases in which orexin receptors are involved. The present invention is also directed to pharmaceutical compositions comprising these compounds. The present invention is also directed to uses of these pharmaceutical compositions in the prevention or treatment of such diseases in which orexin receptors are involved.

  本发明涉及一种与荷尔蒙受体对抗的羟基化合物。本发明还涉及使用此处所述的化合物在潜在的神经和精神障碍和疾病的治疗或预防中所用。本发明还涉及包含这些化合物的药物组合物。本发明还涉及这些药物组合物在预防或治疗与荷尔蒙受体有关的这些疾病中的使用。
• 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.
• US9725434B2
  申请人：——

  公开号：US9725434B2

  公开（公告）日：2017-08-08