R-(-)-3-Methyltetralone | 88745-26-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: R-(-)-3-Methyltetralone
• 英文别名: (R)-3-methyl-3,4-dihydronaphthalen-1(2H)-one；(3R)-3-methyl-3,4-dihydro-2H-naphthalen-1-one
• CAS: 88745-26-0
• 化学式: C₁₁H₁₂O
• 分子量: 160.216
• InChiKey: RKWDIVBLLDITMW-MRVPVSSYSA-N

物化性质

• 沸点：
  118 °C(Press: 6 Torr)
• 密度：
  1.048±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  R-(-)-3-Methyltetralone 在 氢氧化钾 、 PPA 、 盐酸羟胺 作用下， 以 乙醇 为溶剂， 反应 8.0h， 生成 R-(-)-4-Methyl-1,3,4,5-tetrahydrobenzazepin-2-one
  参考文献：
  名称：

  Synthesis and mass-spectrometric behavior of 1,3,4,5-tetrahydrobenz-[b]azepin-2-ones

  摘要：

  DOI：

  10.1007/bf00506886
• 作为产物：
  描述：

  beta-甲基苯丁酸 以60%的产率得到
  参考文献：
  名称：

  TERENTEV, P. B.;VENDROVA, O. E.;DEMYANOVICH, V. M.;SOLOVEVA, L. D.;POTAPO+, XIMIYA GETEROTSIKL. SOEDIN., 1983, N 9, 1236-1239

  摘要：

  DOI：

文献信息

• Rhodium-Catalyzed, Enantioselective Hydroacylation of <i>ortho</i>-Allylbenzaldehydes
  作者：Kirsten F. Johnson、Adam C. Schmidt、Levi M. Stanley

  DOI：10.1021/acs.orglett.5b02559

  日期：2015.10.2

  The development of a rhodium catalyst for endo- and enantioselective hydroacylation of ortho-allylbenzaldehydes is reported. A catalyst generated in situ from [Rh(COD)Cl]2, (R)-DTBM-SEGPHOS, and NaBARF promotes the desired hydroacylation reactions and minimizes the formation of byproducts from competitive alkene isomerization and ene/dehydration pathways. These rhodium-catalyzed processes generate

  铑催化剂的发展内及对映选择性加氢酰化-邻报道-allylbenzaldehydes。由[Rh（COD）Cl] 2，（R）-DTBM-SEGPHOS和NaBARF原位生成的催化剂可促进所需的加氢酰化反应，并使竞争性烯烃异构化和烯/脱水途径形成的副产物最小化。这些铑催化的过程以中等到高的产率（49-91％）产生了3,4-二氢萘-1（2 H）-one产物，并且具有出色的对映选择性（96-99％ee）。
• Origin of Stereocontrol in Guanidine-Bisurea Bifunctional Organocatalyst That Promotes α-Hydroxylation of Tetralone-Derived β-Ketoesters: Asymmetric Synthesis of β- and γ-Substituted Tetralone Derivatives via Organocatalytic Oxidative Kinetic Resolution
  作者：Minami Odagi、Kota Furukori、Yoshiharu Yamamoto、Makoto Sato、Keisuke Iida、Masahiro Yamanaka、Kazuo Nagasawa

  DOI：10.1021/ja511149y

  日期：2015.2.11

  The mechanism of asymmetric a-hydroxylation of tetralone-derived beta-ketoesters with guanidine-bisurea bifunctional organocatalyst in the presence of cumene hydroperoxide (CHP) was examined by means of DFT calculations to understand the origin of the stereocontrol in the reaction. The identified transition-state model was utilized to design an enantioselective synthesis of beta- or gamma-substituted tetralones by catalytic oxidative kinetic resolution reaction of tetralone-derived beta-ketoesters. This kinetic resolution reaction proceeded with high selectivity, and selectivity factors (s value) of up to 99 were obtained. The potential utility of this oxidative kinetic resolution method for synthesis of natural products was confirmed by applying it to achieve an enantioselective synthesis of (+)-linoxepin (13) from beta-substituted tetralone rac-7 in only six steps.
• MEURLING, ANITA, CHEM. SCR., 27,(1987) N 3, 349-354
  作者：MEURLING, ANITA

  DOI：——

  日期：——
• TERENTEV, P. B.;VENDROVA, O. E.;DEMYANOVICH, V. M.;SOLOVEVA, L. D.;POTAPO+, XIMIYA GETEROTSIKL. SOEDIN., 1983, N 9, 1236-1239
  作者：TERENTEV, P. B.、VENDROVA, O. E.、DEMYANOVICH, V. M.、SOLOVEVA, L. D.、POTAPO+

  DOI：——

  日期：——
• Synthesis and mass-spectrometric behavior of 1,3,4,5-tetrahydrobenz-[b]azepin-2-ones
  作者：P. B. Terent'ev、O. E. Vendrova、V. M. Dem'yanovich、L. D. Solov'eva、V. M. Potapov

  DOI：10.1007/bf00506886

  日期：1983.9