(3,4-dihydro-2H-chromen-4-yl)methanol | 33313-82-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (3,4-dihydro-2H-chromen-4-yl)methanol
• 英文别名: chroman-4-yl-methanol；chroman-4-ylmethanol；3,4-dihydro-2H-1-benzopyran-4-ylmethanol；3,4-dihydro-2H-chromen-4-ylmethanol
• CAS: 33313-82-5
• 化学式: C₁₀H₁₂O₂
• mdl: MFCD16293668
• 分子量: 164.204
• InChiKey: JCIBYIVDOVFNJS-UHFFFAOYSA-N

物化性质

• 沸点：
  274.0±19.0 °C(Predicted)
• 密度：
  1.125±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 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：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3,4-dihydro-2H-chromen-4-yl)methanol 在 咪唑 、 三苯基膦二碘化物 作用下， 以 二氯甲烷 为溶剂， 生成 3,4-二氢-4-碘甲基-2H-1-苯并吡喃
  参考文献：
  名称：

  2-Substituted (2SR)-2-Amino-2-((1SR,2SR)-2-carboxycycloprop-1-yl)glycines as Potent and Selective Antagonists of Group II Metabotropic Glutamate Receptors. 1. Effects of Alkyl, Arylalkyl, and Diarylalkyl Substitution

  摘要：

  In this paper, we describe the synthesis of a series of a-substituted analogues of the potent and selective group II metabotropic glutamate receptor (mGluR) agonist (1S,1'S,2'S)-carboxy-cyclopropylglycine (2, L-CCG 1). Incorporation of a substituent on the amino acid carbon converted the agonist 2 into antagonist. Ail of the compounds were prepared and tested as a series of four isomers, i.e., two racemic diastereomers. We explored alkyl substitution, both normal and terminally branched; phenylalkyl and diphenylalkyl substitution; and a variety of aromatic and carbocyclic surrogates for phenyl. Affinity for group II mGluRs was measured using [H-3]glutamic acid (Glu) binding in rat forebrain membranes. Antagonist activity was confirmed for these compounds by measuring their ability to antagonize (1S,3R)-1-aminocyclopentane-1,3-dicarboxylic acid-induced inhibition of forskolin-stimulated cyclic-AMP in RGT cells transfected with human mGluR2 and mGluR3. We found that while alkyl substitution provided no increase in affinity relative to 2, phenylethyl and diphenylethyl substitution, as in 105 and 109, respectively, were quite beneficial, The affinity of 109 was further enhanced when the two aromatic rings were joined by an oxygen or sulfur atom to form the tricyclic xanthylmethyl and thioxanthylmethyl amino acids 113 and 114, respectively. Amino acid 113, with an IC50 of 0.10 mu M in the [H-3]Glu binding assay, was 52-fold more patent than 2, whose IC50 was 0.47 mu M.

  DOI：

  10.1021/jm970497w
• 作为产物：
  描述：

  2,3-二氢苯并吡喃-4-酮 在 硼烷四氢呋喃络合物 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 生成 (3,4-dihydro-2H-chromen-4-yl)methanol
  参考文献：
  名称：

  [EN] COMPOUNDS AND COMPOSITIONS FOR TREATING CNS DISORDERS
  [FR] COMPOSÉS ET COMPOSITIONS POUR LE TRAITEMENT DE TROUBLES DU SYSTÈME NERVEUX CENTRAL

  摘要：

  本公开提供化合物及其制药组合物。还提供制备和使用这些化合物的方法。这些化合物可以用于调节，例如激活TAAR1，并可用于治疗、预防、诊断和/或管理各种中枢神经系统疾病。

  公开号：

  WO2022204150A1

文献信息

• [EN] DUAL NAV1.2/5HT2A INHIBITORS FOR TREATING CNS DISORDERS<br/>[FR] INHIBITEURS DOUBLES DE NAV1.2/5HT2A POUR TRAITER DES TROUBLES DU SNC
  申请人：SUNOVION PHARMACEUTICALS INC

  公开号：WO2018026371A1

  公开（公告）日：2018-02-08

  Compounds of formula I: I are disclosed, as are pharmaceutical compositions containing such compounds. Methods of treating neurological or psychiatric disorders in a patient in need are also disclosed. Such disorders include depression, bipolar disorder, pain, schizophrenia, obsessive compulsive disorder, addiction, social disorder, attention deficit hyperactivity disorder, an anxiety disorder, autism, a cognitive impairment, or a neuropsychiatric symptom such as apathy, depression, anxiety, psychosis, aggression, agitation, impulse control disorders, and sleep disorders in neurological disorders such as Alzheimer's and Parkinson's diseases.

  公开了化学式I的化合物，以及含有这些化合物的药物组合物。还公开了治疗患有神经系统或精神障碍的患者的方法。这些障碍包括抑郁症、躁郁症、疼痛、精神分裂症、强迫症、成瘾、社交障碍、注意力缺陷多动障碍、焦虑障碍、自闭症、认知障碍，或神经精神症状，如冷漠、抑郁、焦虑、精神病、攻击性、激动、冲动控制障碍，以及在神经系统疾病如阿尔茨海默病和帕金森病中的睡眠障碍。
• [EN] HISTONE DEMETHYLASE INHIBITORS<br/>[FR] INHIBITEURS D'HISTONE DÉMÉTHYLASE
  申请人：QUANTICEL PHARMACEUTICALS INC

  公开号：WO2014151106A1

  公开（公告）日：2014-09-25

  The present invention relates generally to compositions and methods for treating cancer and neoplastic disease. Provided herein are substituted pyrido[3,4-d]pyrimidin-4-one derivative compounds and pharmaceutical compositions comprising said compounds. The subject compounds and compositions are useful for inhibition of histone demethylase. Furthermore, the subject compounds and compositions are useful for the treatment of cancer, such as prostate cancer, breast cancer, bladder cancer, lung cancer and/or melanoma and the like.

  本发明一般涉及治疗癌症和肿瘤性疾病的组合物和方法。本文提供了取代的吡啶并[3,4-d]嘧啶-4-酮衍生物化合物和包含该化合物的药物组合物。所述化合物和组合物对组蛋白去甲基化酶的抑制具有用处。此外，所述化合物和组合物对癌症的治疗有用，如前列腺癌、乳腺癌、膀胱癌、肺癌和/或黑色素瘤等。
• Oxidative rearrangement of alkenes using in situ generated hypervalent iodine(III)
  作者：Anees Ahmad、Paulo Scarassati、Nazli Jalalian、Berit Olofsson、Luiz F. Silva

  DOI：10.1016/j.tetlet.2013.08.012

  日期：2013.10

  A novel protocol for the oxidative rearrangement of alkenes using in situ generated hypervalent iodine(III) was developed. This approach uses inexpensive, readily available, and stable chemicals (PhI, mCPBA, and TsOH) giving rearrangement products in yields comparable to those obtained using the more expensive commercially available [hydroxy(tosyloxy)iodo]benzene [HTIB or Koser’s reagent]. Additionally

  建立了一种使用原位生成的高价碘（III）进行烯烃氧化重排的新方案。这种方法使用廉价，易于获得且稳定的化学品（PhI，m CPBA和TsOH），可提供重排产物，其收率可与使用较昂贵的市售[羟基（甲苯磺酰氧基）碘]苯[HTIB或Koser试剂]获得的产率相当。另外，对于1-甲基-2-四氢萘酮通过使用4-甲基-1,2-二氢萘的一步法环氧化/重排合成的替代协议米CPBA和TsOH被开发。
• Synthesis of benzofurans, indoles and benzopyrans via oxidative free radical cyclisations using cobalt salen complexes.
  作者：Vinod F. Patel、Gerald Pattenden、Jamie J. Russell

  DOI：10.1016/s0040-4039(00)84514-1

  日期：——

  species derived from cobalt(III) ‘salen’(1), and (O-allyl) or (O-but-3-enyl) iodophenol, leads to isolatable cobalt complexes, viz (2), (13), which can be converted into substituted benzofurans, i .e. (5), (6) and benzopyrans, i .e. (14), (15); similarly interaction between (18) and Co(I) ‘salen’ led, in one step, to the 3-methylindole (19).

  衍生自钴（III）'salen'（1）的Co（I）物种与（O-烯丙基）或（O-but-3-enyl）碘苯酚之间的反应导致可分离的钴络合物，即（2）， （13），它可以转化为取代的苯并呋喃，即 （5），（6）和苯并吡喃，即 （14），（15）；类似地，（18）和Co（I）“ salen”之间的相互作用一步就产生了3-甲基吲哚（19）。
• Exploiting sequential lipase-catalyzed reactions to achieve enantiomerically pure chiral primary alcohols
  作者：Rodrigo S. Martins、Anees Ahmad、Luiz F. Silva、Leandro H. Andrade

  DOI：10.1039/c5ra06469d

  日期：——

  cycloalkane-containing primary alcohols with vinyl acetate was performed and allowed the isolation of enantiopure alcohols. Lipases from P. cepacia, C. rugosa, C. antarctica, P. fluorescens, C. cylindracea and M. miehei exhibited remarkable activity towards acetylation of these alcohols, affording the corresponding acetates with high conversion. Due to the high lipase activity toward primary alcohols, the enantioselectivity

  用乙酸乙烯酯对含苯并稠合的环烷烃的伯醇进行脂肪酶催化的对映选择性乙酰化，并分离出对映纯的醇。洋葱，南美白对虾，南极南美白对虾，萤光假单胞菌，圆柱状对虾和小黑背对虾的脂肪酶对这些醇的乙酰化显示出显着的活性，从而提供了具有高转化率的相应乙酸酯。由于对伯醇的高脂肪酶活性，对映选择性低。为了解决这个问题，采用对映体互补脂肪酶进行顺序动力学拆分，得到对映体纯的伯醇。该方法代表了一种获得带有环体系的手性结构单元的新方法，例如茚满，苯并二氢吡喃和四氢萘。