(5R,2Z)-5-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-6-oxo-2-hexenoic acid | 1189368-35-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (5R,2Z)-5-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-6-oxo-2-hexenoic acid
• 英文别名: (5R,2Z)-5-[dimethyl(1,1,2-trimethylpropyl)silyloxy]-6-oxo-2-hexenoic acid
• CAS: 1189368-35-1
• 化学式: C₁₄H₂₆O₄Si
• 分子量: 286.444
• InChiKey: HTLCJEZHYSEWKJ-ZVTBTPLYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.24
• 重原子数：
  19.0
• 可旋转键数：
  8.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  63.6
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (5R,2Z)-5-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-6-oxo-2-hexenoic acid 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 三乙胺 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 生成
  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：

  (1R,2R,3R)-1-O-[dimethyl(1,1,2-trimethylpropyl)silyl]-2,3-O-isopropylidenecyclohex-4-ene-1,2,3-triol 在 copper(II) choride dihydrate 、 SiO₂-supported NaIO₄ 、 2-碘酰基苯甲酸 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 生成 (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

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.