(2Z,5R,6S)-5-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-6-hydroxy-cyclohex-2-enone | 1189368-33-9

• 分子结构分类: 有机化合物
• 英文名称: (2Z,5R,6S)-5-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-6-hydroxy-cyclohex-2-enone
• 英文别名: (5R,6S)-5-[dimethyl(1,1,2-trimethylpropyl)silyloxy]-6-hydroxycyclohex-2-ene-1-one
• CAS: 1189368-33-9
• 化学式: C₁₄H₂₆O₃Si
• 分子量: 270.444
• InChiKey: CMHZKNSDPFVTOU-CHWSQXEVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (2Z,5R,6S)-5-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-6-hydroxy-cyclohex-2-enone 在 SiO₂-supported NaIO₄ 作用下， 以 neat (no solvent) 为溶剂， 以90%的产率得到(5R,2Z)-5-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-6-oxo-2-hexenoic acid
  参考文献：
  名称：

  Chemoenzymatic preparation of (6R)-5,6-dihydro-2H-pyran-2-one: a ubiquitous structural motif of biologically active lactones

  摘要：

  A chemoenzymatic synthesis of an enantiopure 6-substituted 5,6-dihydro-2H-pyran-2-one using bromobenzene as a starting material is presented. This important structural motif is found in a large number of chiral lactones that present a wide range of biological activities. The key features of the preparation include enzymatic dioxygenation of bromobenzene using Escherichia coli JM109 (pDTG601), microwave-assisted acyloin cleavage, and tin mediated lactonization. The stereochemical assignment for the alcohol was confirmed by NMR analysis of Moshers derivatives. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.10.005
• 作为产物：
  描述：

  (1S,2S,3R)-4-Bromo-2,3-O-isopropylidenecyclohex-4-ene-1,2,3-triol 在 咪唑 、 copper(II) choride dihydrate 、 偶氮二异丁腈 、 三正丁基氢锡 、 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成 (2Z,5R,6S)-5-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-6-hydroxy-cyclohex-2-enone
  参考文献：
  名称：

  Chemoenzymatic preparation of (6R)-5,6-dihydro-2H-pyran-2-one: a ubiquitous structural motif of biologically active lactones

  摘要：

  A chemoenzymatic synthesis of an enantiopure 6-substituted 5,6-dihydro-2H-pyran-2-one using bromobenzene as a starting material is presented. This important structural motif is found in a large number of chiral lactones that present a wide range of biological activities. The key features of the preparation include enzymatic dioxygenation of bromobenzene using Escherichia coli JM109 (pDTG601), microwave-assisted acyloin cleavage, and tin mediated lactonization. The stereochemical assignment for the alcohol was confirmed by NMR analysis of Moshers derivatives. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.10.005

文献信息

• Microwave-assisted, solvent-free oxidative cleavage of α-hydroxyketones
  作者：Ignacio Carrera、Margarita C. Brovetto、Juan Carlos Ramos、Gustavo A. Seoane

  DOI：10.1016/j.tetlet.2009.07.048

  日期：2009.9

  The oxidative C-C cleavage of alpha-hydroxy ketones was found to proceed smoothly in solvent-free, silica-supported sodium metaperiodate, under Microwave irradiation. This provides a useful and green synthetic procedure to form the corresponding carboxylic acid and aldehyde in good yields, avoiding the solubility problems of the sodium metaperiodate in organic solvents. (C) 2009 Elsevier Ltd. All rights reserved.