(±)-2-(m-tolyl)cyclopentan-1-one | 52086-33-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (±)-2-(m-tolyl)cyclopentan-1-one
• 英文别名: 2-(m-tolyl)cyclopentanone；2-(m-Tolyl)-cyclopentanon；2-(3-Methylphenyl)cyclopentan-1-one
• CAS: 52086-33-6
• 化学式: C₁₂H₁₄O
• 分子量: 174.243
• InChiKey: IKRZOMCGYVFIEC-UHFFFAOYSA-N

物化性质

• 沸点：
  293.4±29.0 °C(Predicted)
• 密度：
  1.051±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：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (±)-2-(m-tolyl)cyclopentan-1-one 在 氢气 、 三乙酰氧基硼氢化钠 、 溶剂黄146 作用下， 以 甲醇 、 1,2-二氯乙烷 为溶剂， 反应 66.0h， 生成 (1R,2R)-2-(3-methylphenyl)cyclopentan-1-amine
  参考文献：
  名称：

  The identification of 7-[(R)-2-((1S,2S)-2-benzyloxycyclopentylamino)-1-hydroxyethyl]-4-hydroxybenzothiazolone as an inhaled long-acting β2-adrenoceptor agonist

  摘要：

  The optimisation of two series of 4-hydroxybenzothiazolone derived β2-adrenoceptor agonists, bearing α-substituted cyclopentyl and β-phenethyl amino-substituents, as inhaled long-acting bronchodilators is described. Analogues were selected for synthesis using a lipophilicity based hypothesis to achieve the targeted rapid onset of action in combination with a long duration of action. The profiling of the two series led to identification of the α-substituted cyclopentyl analogue 2 as the optimal compound with a comparable profile to the inhaled once-daily long-acting β2-adrenoceptor agonist indacaterol. On the basis of these data 2 was promoted as the backup development candidate to indacaterol from the Novartis LABA project.

  DOI：

  10.1016/j.bmcl.2014.06.014
• 作为产物：
  描述：

  3-溴甲基苯 在 甲酸 、 双氧水 、 对甲苯磺酸 、 magnesium 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 10.0h， 生成 (±)-2-(m-tolyl)cyclopentan-1-one
  参考文献：
  名称：

  区域和对映选择性拜耳-维利格氧化：外消旋2-取代的环戊烷酮的动力学拆分。

  摘要：

  通过高度区域和对映选择性的Baeyer-Villiger氧化，成功开发了外消旋2-取代的环戊酮的动力学拆分。该反应可提供高达98％ee和> 19/1区域选择性的正常6-取代的δ-内酯。同时，未反应的酮以优异的ee值（高达98％）被回收。它代表通过非酶不对称BV氧化动力学拆分外消旋2取代的环戊酮的最佳结果。

  DOI：

  10.1021/ol501737a

文献信息

• Practical Direct α-Arylation of Cyclopentanones by Palladium/Enamine Cooperative Catalysis
  作者：Yan Xu、Tianshun Su、Zhongxing Huang、Guangbin Dong

  DOI：10.1002/anie.201510638

  日期：2016.2.12

  Direct arylation of cyclopentanones has been a long‐standing challenge because of competitive self‐aldol condensation and multiple arylations. Reported herein is a direct mono‐α‐C−H arylation of cyclopentanones with aryl bromides which is enabled by palladium/amine cooperative catalysis. This method is scalable and chemoselective with broad functional‐group tolerance. Application to controlled sequential

  由于竞争性的自我醛醇缩合和多种芳基化，环戊酮的直接芳基化一直是一个长期的挑战。本文报道的是环戊酮与芳基溴化物的直接单α-CH芳基化反应，这是通过钯/胺协同催化实现的。该方法具有可扩展性和化学选择性，并具有广泛的功能组耐受性。还证明了其在环戊酮的受控顺序芳基化中的应用。
• Organocatalytic asymmetric Michael addition of α-aryl cyclopentanones to nitroolefins for construction of adjacent quaternary and tertiary stereocenters
  作者：Xiu-Qin Dong、Huai-Long Teng、Min-Chao Tong、He Huang、Hai-Yan Tao、Chun-Jiang Wang

  DOI：10.1039/c0cc01987a

  日期：——

  The first asymmetric Michael addition of alpha-aryl cyclopentanones to nitroolefins for construction of adjacent quaternary and tertiary stereocenters has been achieved with excellent diastereo-/enantioselectivity.

  首次以非对映体/对映体选择性实现了将α-芳基环戊烯酮不对称迈克尔加成到硝基烯烃中以构建相邻的季和叔立体中心。
• Caubere,P. et al., Bulletin de la Societe Chimique de France, 1973, p. 3493 - 3497
  作者：Caubere,P. et al.

  DOI：——

  日期：——
• Studies on diastereoselective additions of 2-substituted cyclopentanones to ?-nitrostyrene
  作者：J. Deutsch、H.-J. Niclas、M. Ramm

  DOI：10.1002/prac.19953370105

  日期：——

  The Michael addition of 2-substituted cyclopentanones 1 to beta-nitrostyrene 2 proceeds at room temperature in the presence of catalysts such as NEt(3), DMAP, KOAc, or Ni(acac)(2) leading to 2-substituted 2-(2-nitro-1-phenylethyl)cyclopentanones 3/4. Depending on substituents R in 1 compounds rac-3/4 may be obtained with high diastereoselectivity. The influences of reaction conditions were studied and the diastereomeric ratio was determined by means of H-1-NMR spectroscopy. In the cases of rac-3/4a-c, rac-3g-i, rac-3k, the diastereomers could be isolated in pure form. The configuration of compounds rac-3a and rac-4a was established from X-ray crystallography.