1-Methyl-1-phenyl-cycloheptanon-(2) | 22612-77-7

• 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: 1-Methyl-1-phenyl-cycloheptanon-(2)
• 英文别名: 2-Methyl-2-phenyl-cycloheptanon；2-Methyl-2-phenylcycloheptan-1-one；2-methyl-2-phenylcycloheptan-1-one
• CAS: 22612-77-7
• 化学式: C₁₄H₁₈O
• 分子量: 202.296
• InChiKey: TVYGHBBXIHAIOM-UHFFFAOYSA-N

物化性质

• 沸点：
  164 °C(Press: 11 Torr)
• 密度：
  1.0294 g/cm3(Temp: 25 °C)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  1-Methyl-1-phenyl-cycloheptanon-(2) 在 氢氧化钾 、 肼 、 二乙二醇 作用下， 生成 1-Methyl-1-phenyl-cycloheptan
  参考文献：
  名称：

  Ring-Size Effects in the Neophyl Rearrangement. VI.¹ The 1-Phenylcycloheptylcarbinyl System

  摘要：

  DOI：

  10.1021/jo01341a055
• 作为产物：
  描述：

  2-甲基-2-苯基-1,3-二氧戊环 在 萘 、 磷酸 、 lithium 作用下， 以 甲苯 为溶剂， 反应 15.75h， 生成 1-Methyl-1-phenyl-cycloheptanon-(2)
  参考文献：
  名称：

  Reductive opening of 2-phenyl-1,3-dioxolanes by a naphthalene-catalysed lithiation: synthetic applications

  摘要：

  The reaction of 2-phenyl-1,3-dioxolanes 1a,b with an excess of lithium powder in the presence of a catalytic amount of naphthalene (4 mol %) in tetrahydrofuran at -40-degrees-C followed by successive reaction with an electrophile and final hydrolysis with water at the same temperature yields the corresponding monoprotected 1,2-diols 2aa-2bf. The same process but allowing to rise the temperature to 20-degrees-C before the hydrolysis affords alcohols 3aa-3bd. The use of 2,2-diphenyl-1,3-dioxolane 1d, under similar reaction conditions as for compounds 2, permits the isolation of 2,2-diphenylalcohols 11da-11dc, resulting from the reaction with two different electrophiles. A mechanistic rationalization for all processes is given.

  DOI：

  10.1016/s0040-4020(01)80223-4

文献信息

• Highly Efficient and Enantioselective α-Arylation of Cycloalkanones by Scandium-Catalyzed Diazoalkane-Carbonyl Homologation
  作者：Jason Kingsbury、Victor Rendina、Hilan Kaplan

  DOI：10.1055/s-0031-1289650

  日期：2012.3

  Functionalized α-tertiary and -quaternary 2-arylcycloalkanones are rapidly accessed by scandium(III) triflate-catalyzed diazo­alkane-carbonyl homologations. Recent developments have allowed for carbon insertion reactions to be performed with catalyst loadings as low as 0.5 mol% on scales up to 5 mmol. Pairing readily available bis- and tris(oxazoline) based ligands with scandium triflate allows access to arylated medium ring carbocycles with enantioselectivities up to 98:2 er and >98% yield. The formal C-C insertion of aryldiazo­methanes into unsubstituted cycloalkanones provides a single-step solution to the ongoing challenge of α-arylation.

  功能化的α-叔和α-季2-芳基环烷酮通过三氟甲磺酸钪(III)催化的重氮甲烷-羰基同系化反应迅速获得。最近的进展使得碳插入反应能够在催化剂负载量低至0.5 mol%的情况下进行，规模可达5 mmol。结合易于获得的基于双和三噁唑啉的配体与三氟甲磺酸钪，可以合成具有高达98:2 对映体比和>98%产率的芳基化中环碳环。芳基重氮甲烷在无取代环烷酮中的正式C-C插入提供了一种一步解决α-芳基化持续挑战的方法。
• Mg-promoted mixed pinacol coupling
  作者：Hirofumi Maekawa、Yoshimasa Yamamoto、Hisashi Shimada、Kazuaki Yonemura、Ikuzo Nishiguchi

  DOI：10.1016/j.tetlet.2004.03.109

  日期：2004.5

  Mg-promoted reduction of a mixture of aromatic ketones (or imines) and aliphatic carbonyl compounds in N,N-dimethylformamide (DMF) brought about unique mixed pinacol type of cross coupling to give unsymmetrical vicinal diols (or amino alcohols) or α-hydroxyketones in good to moderate yields. The reaction may be initiated by electron transfer from magnesium metal to an aromatic carbonyl compound possessing a

  镁促进的N，N-二甲基甲酰胺（DMF）中芳香族酮（或亚胺）和脂肪族羰基化合物混合物的还原反应产生独特的混合频哪醇类型的交叉偶联，从而得到不对称的邻位二醇（或氨基醇）或α-羟基酮中等至中等的产量。该反应可以通过电子从镁金属转移到具有较小的负还原电位的芳族羰基化合物而引发。发现芳族酮（或亚胺）与脂族羰基化合物之间的还原电势差是这种选择性交叉偶联的重要关键因素之一。
• Catalytic Diazoalkane-Carbonyl Homologation: Synthesis of 2,2-Diphenylcycloheptanone and Other Quaternary or Tertiary Arylalkanones and Spirocycles by Ring Expansion
  作者：Jason S. Kingsbury

  DOI：10.15227/orgsyn.098.0343

  日期：——
• Molecular Rearrangements. IV. The Pinacol Rearrangement of 1-Hydroxy-1-cyclohexylmethylphenylcarbinol¹
  作者：Gloria G. Lyle、Rupert A. Covey、Robert E. Lyle

  DOI：10.1021/ja01639a036

  日期：1954.5
• Reductive opening of 2-phenyl-1,3-dioxolanes by a naphthalene-catalysed lithiation: synthetic applications
  作者：Juan F. Gil、Diego J. Ramón、Miguel Yus

  DOI：10.1016/s0040-4020(01)80223-4

  日期：——

  The reaction of 2-phenyl-1,3-dioxolanes 1a,b with an excess of lithium powder in the presence of a catalytic amount of naphthalene (4 mol %) in tetrahydrofuran at -40-degrees-C followed by successive reaction with an electrophile and final hydrolysis with water at the same temperature yields the corresponding monoprotected 1,2-diols 2aa-2bf. The same process but allowing to rise the temperature to 20-degrees-C before the hydrolysis affords alcohols 3aa-3bd. The use of 2,2-diphenyl-1,3-dioxolane 1d, under similar reaction conditions as for compounds 2, permits the isolation of 2,2-diphenylalcohols 11da-11dc, resulting from the reaction with two different electrophiles. A mechanistic rationalization for all processes is given.