3-o-chlorophenyl-1-tetralone | 118806-82-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 3-o-chlorophenyl-1-tetralone
• 英文别名: 3-(2-chlorophenyl)-3,4-dihydro-2H-naphthalen-1-one
• CAS: 118806-82-9
• 化学式: C₁₆H₁₃ClO
• 分子量: 256.732
• InChiKey: MOJIHCPNIQRHOD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 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：

  3-o-chlorophenyl-1-tetralone 在 过氧化氢异丙苯 、 C₅₃H₆₅F₁₂N₇O₂*ClH 、 sodium hydride 、 potassium carbonate 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲苯 、 mineral oil 为溶剂， 反应 49.5h， 生成
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1021/ja511149y
• 作为产物：
  描述：

  2-(2-氯苄亚基)丙二酸二乙酯 在 氢氧化钾 、 PPA 、 Polyphosphoric acid (PPA) 、 硫酸 、 copper(l) chloride 作用下， 以 乙醚 为溶剂， 反应 15.0h， 生成 3-o-chlorophenyl-1-tetralone
  参考文献：
  名称：

  Selvaraj, S.; Rajendran, A. S.; Arumugam, N., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1987, vol. 26, # 1-12, p. 1047 - 1049

  摘要：

  DOI：

文献信息

• Selvaraj, S.; Ramakrishnan, P. S.; Arumugam, N., Recueil des Travaux Chimiques des Pays-Bas, 1989, vol. 108, # 1, p. 36 - 37
  作者：Selvaraj, S.、Ramakrishnan, P. S.、Arumugam, N.

  DOI：——

  日期：——
• SELVARAJ, S.;RAMAKRISHNAN, P. S.;ARUMUGAM, N., REC. TRAV. CHIM. PAYS-BAS, 108,(1989) N, C. 36-37
  作者：SELVARAJ, S.、RAMAKRISHNAN, P. S.、ARUMUGAM, N.

  DOI：——

  日期：——
• SELVARAJ, S.;RAJENDRAN, A. S.;ARUMUNGAM, N., INDIAN J. CHEM., 26,(1987) N 11, 1047-1049
  作者：SELVARAJ, S.、RAJENDRAN, A. S.、ARUMUNGAM, N.

  DOI：——

  日期：——