(-)-((4R,5R)-2,2-dimethyl-5-(4-methyl-benzoyl)-[1,3]dioxolan-4-yl)-p-tolyl-methanone | 861853-89-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (-)-((4R,5R)-2,2-dimethyl-5-(4-methyl-benzoyl)-[1,3]dioxolan-4-yl)-p-tolyl-methanone
• 英文别名: (4R,5R)-2,2-dimethyl-4,5-bis(4-methylbenzoyl)-1,3-dioxolane
• CAS: 861853-89-6
• 化学式: C₂₁H₂₂O₄
• 分子量: 338.403
• InChiKey: VZFZNHSAORLKKL-PMACEKPBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.89
• 重原子数：
  25.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (-)-((4R,5R)-2,2-dimethyl-5-(4-methyl-benzoyl)-[1,3]dioxolan-4-yl)-p-tolyl-methanone 在 lead(IV) acetate 、 sodium tetrahydroborate 、 18-冠醚-6 、 三氯化铁 、 potassium tri-sec-butyl-borohydride 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 苯 为溶剂， 反应 6.0h， 生成 (R)-2-Methoxy-2-p-tolyl-ethanol
  参考文献：
  名称：

  Asymmetric synthesis of α-methoxyarylacetic acid derivatives

  摘要：

  Stereoselective synthesis of a series of 2-aryl-2-methoxyethanols was achieved from inexpensive chiral pool tartaric acid employing a diastereoselective reduction of a symmetrical 1,4-diaryldiketone as the key step. 2-Aryl-2-methoxyethanols were enantioselectively prepared in 80-90% yield (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.05.002
• 作为产物：
  描述：

  (4R,5R)-4,5-二(二甲氨基羰基)-2,2-二甲基二氧 、 对甲苯基溴化镁 以 四氢呋喃 为溶剂， 以53%的产率得到(-)-((4R,5R)-2,2-dimethyl-5-(4-methyl-benzoyl)-[1,3]dioxolan-4-yl)-p-tolyl-methanone
  参考文献：
  名称：

  Asymmetric synthesis of α-methoxyarylacetic acid derivatives

  摘要：

  Stereoselective synthesis of a series of 2-aryl-2-methoxyethanols was achieved from inexpensive chiral pool tartaric acid employing a diastereoselective reduction of a symmetrical 1,4-diaryldiketone as the key step. 2-Aryl-2-methoxyethanols were enantioselectively prepared in 80-90% yield (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.05.002

文献信息

• Synthesis of Enantiopure Trifluoromethyl Building Blocks via a Highly Chemo- and Diastereoselective Nucleophilic Trifluoromethylation of Tartaric Acid-Derived Diketones
  作者：Fabien Massicot、Nicolas Monnier-Benoit、Naba Deka、Richard Plantier-Royon、Charles Portella

  DOI：10.1021/jo062016z

  日期：2007.2.1

  acid-based diketone, using trifluoromethyl(trimethyl)silane, afforded the corresponding γ-keto trifluoromethylcarbinol. The scope and limitation of this reaction was studied. The acidic removal of the acetonide moiety protecting the two hydroxyl groups of the adducts was unsuccessful. Bis(O-methylation) of the aromatic derivatives under basic conditions, followed by acidic hydrolysis and oxidative cleavage

  基于酒石酸的二酮的高度非对映选择性亲核性单（三氟甲基化），使用三氟甲基（三甲基）硅烷，得到了相应的γ-酮基三氟甲基甲醇。研究了该反应的范围和局限性。酸性除去保护加合物的两个羟基的丙酮化物部分是不成功的。在碱性条件下，芳族衍生物的双（O-甲基化），然后进行酸性水解和氧化裂解，产生两种不同的对映体纯产物：α-芳基-α-甲氧基-α-三氟甲基乙醛和α-芳基-α-甲氧基羧酸。最终，整个过程是将一种天然手性原料转化为两种功能化的对映纯结构单元（包括三氟甲基单元）的有趣方法。
• Nucleophilic Addition Reactions of 1,4-Diketones Derived from Tartaric Acid: Synthesis of TADDOL Analogues
  作者：Kavirayani Prasad、Appayee Chandrakumar

  DOI：10.1055/s-2006-942422

  日期：2006.7

  A systematic investigation of the reduction and Grignard reagents addition to 1,4-diketones derived from tartaric acid was carried out. It was found that the reduction proceeded with high selectivity using K-Selectride as the reducing agent; while Grignard reagent addition was highly dependent on structure of the dione as well as on the Grignard reagent. The resultant 1,4-diols represent a series of novel TADDOL analogues.

  对酒石酸衍生的 1,4-二酮的还原和格氏试剂添加进行了系统研究。研究发现，使用 K-选择性氮化物作为还原剂，还原过程具有很高的选择性；而格氏试剂的加成则高度依赖于二酮的结构以及格氏试剂。由此产生的 1,4 二醇代表了一系列新型 TADDOL 类似物。