(-)-menthyl 1-tetralone-2-carboxylate | 283174-81-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (-)-menthyl 1-tetralone-2-carboxylate
• 英文别名: L-menthyl 1-tetralone-2-carboxylate；[(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl] 1-oxo-3,4-dihydro-2H-naphthalene-2-carboxylate
• CAS: 283174-81-2
• 化学式: C₂₁H₂₈O₃
• 分子量: 328.452
• InChiKey: KSJWIWBWAQRKOZ-ZCRYQTBPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (-)-menthyl 1-tetralone-2-carboxylate 在 sodium hydride 、 Selectfluor 作用下， 生成 (1'R,2'S,5'R)-(-)-menthyl 2R-fluoro-1-tetralone-2-carboxylate 、 (1'R,2'S,5'R)-(-)-menthyl 2S-fluoro-1-tetralone-2-carboxylate
  参考文献：
  名称：

  Epoxidation with dioxiranes derived from 2-fluoro-2-substituted-1-tetralones and -1-indanones

  摘要：

  Homochiral 2-fluoro-2-substituted-1-tetralones (10a, 10b, 13) and ethyl 2-fluoro-1-indanone-2-carboxylate (16) have been isolated. The dioxirane derivatives of these ketones have been prepared in situ, and have been shown to epoxidise alkenes but not enantioselectively. The dioxirane derivative of methyl 2,5,7-trifluoro-1-indanone-2-carboxylate (18) has been shown to be comparatively efficient in epoxidation.

  DOI：

  10.1016/0040-4020(95)00075-j
• 作为产物：
  描述：

  L-薄荷醇 、 1,2,3,4-四氢-1-氧代-2-萘羧酸甲酯 在 4-二甲氨基吡啶 作用下， 以 环己烷 为溶剂， 以63%的产率得到(-)-menthyl 1-tetralone-2-carboxylate
  参考文献：
  名称：

  β-酮酯的共沸酯交换

  摘要：

  由 DMAP 催化的 β-酮羧酸甲酯与各种高沸点醇的酯交换可以在迪安-斯达克分水器中回流环己烷中完成。形成的MeOH作为共沸物从反应混合物中完全去除，导致定量转化。原料以化学计量比进行转化，这使得产物的纯化非常简单并导致高产率。

  DOI：

  10.1002/(sici)1099-0690(200004)2000:8<1633::aid-ejoc1633>3.0.co;2-w

文献信息

• Azeotropic Transesterification of β-Keto Esters
  作者：Jens Christoffers、Neclâ Önal

  DOI：10.1002/(sici)1099-0690(200004)2000:8<1633::aid-ejoc1633>3.0.co;2-w

  日期：2000.4

  Transesterifications of methyl β-keto carboxylates catalyzed by DMAP with various high boiling alcohols can be accomplished in refluxing cyclohexane in a Dean-Stark trap. The MeOH formed is removed completely from the reaction mixture as an azeotrope leading to quantitative conversions. The starting materials are converted in stoichiometric ratio, which makes the purification of the product very simple

  由 DMAP 催化的 β-酮羧酸甲酯与各种高沸点醇的酯交换可以在迪安-斯达克分水器中回流环己烷中完成。形成的MeOH作为共沸物从反应混合物中完全去除，导致定量转化。原料以化学计量比进行转化，这使得产物的纯化非常简单并导致高产率。
• Christoffers, Jens; Oertling, Heiko; Oenal, Necla, Advanced Synthesis and Catalysis, 2000, vol. 342, # 6, p. 546 - 553
  作者：Christoffers, Jens、Oertling, Heiko、Oenal, Necla

  DOI：——

  日期：——
• Epoxidation with dioxiranes derived from 2-fluoro-2-substituted-1-tetralones and -1-indanones
  作者：David S. Brown、Brian A. Marples、Paul Smith、Lesley Walton

  DOI：10.1016/0040-4020(95)00075-j

  日期：1995.3

  Homochiral 2-fluoro-2-substituted-1-tetralones (10a, 10b, 13) and ethyl 2-fluoro-1-indanone-2-carboxylate (16) have been isolated. The dioxirane derivatives of these ketones have been prepared in situ, and have been shown to epoxidise alkenes but not enantioselectively. The dioxirane derivative of methyl 2,5,7-trifluoro-1-indanone-2-carboxylate (18) has been shown to be comparatively efficient in epoxidation.
• Highly Enantioselective Chlorination of β-Keto Esters and Subsequent S_N2 Displacement of Tertiary Chlorides: A Flexible Method for the Construction of Quaternary Stereogenic Centers
  作者：Kazutaka Shibatomi、Yoshinori Soga、Akira Narayama、Ikuhide Fujisawa、Seiji Iwasa

  DOI：10.1021/ja304806j

  日期：2012.6.20

  Highly enantioselective chlorination of beta-oxo esters and subsequent stereospecific substitution of tertiary chlorides are described. Enantioselective chlorination of beta-keto esters and malonates was performed using a chiral Lewis acid catalyst prepared from Cu(OTf)(2) and the newly developed spirooxazoline ligand 2 to yield the desired a-chlorinated products with high enantioselectivity (up to 98% ee). Nucleophilic substitution of the resulting chlorides proceeded smoothly to afford a variety of chiral molecules such as alpha-amino, alpha-allcylthio, and alpha-fluoro esters, without loss of enantiopurity. The results of X-ray crystallographic analysis proved that Walden inversion occurs at the chlorinated tertiary carbon center. These results supported the fact that the substitution proceeds via an S(N)2 mechanism.