propargyl (5S,6R)-5,6-dihydroxy-2-bromocyclohexa-1,3-dienecarboxylate | 1558039-86-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: propargyl (5S,6R)-5,6-dihydroxy-2-bromocyclohexa-1,3-dienecarboxylate
• CAS: 1558039-86-3
• 化学式: C₁₀H₉BrO₄
• 分子量: 273.083
• InChiKey: OQBIQIMWIKKHLR-CBAPKCEASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  15.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  66.76
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  prop-2-yn-1-yl 2-bromobenzoate 在 toluene dioxygenase from E_. coli JM₁₀₉ (pDTG₆₀₁A) 作用下， 反应 3.0h， 生成 propargyl (5S,6R)-5,6-dihydroxy-2-bromocyclohexa-1,3-dienecarboxylate
  参考文献：
  名称：

  Processing of o-Halobenzoates by Toluene Dioxygenase. The Role of the Alkoxy Functionality in the Regioselectivity of the Enzymatic Dihydroxylation Reaction

  摘要：

  In order to investigate the relationship between the size of a substituent on the aromatic substrate and its directing effect on the dihydroxylation, a series of 2-halobenzoates was synthesized and subjected to metabolism by toluene dioxygenase in preparative-scale fermentation cultures of Escherichia coli JM109 (pDTG601A). Larger ester substituents were shown to have a greater directing effect on the dihydroxylation reaction. Furthermore, significant increases in regioselectivity were observed using propargyl substituents, relative to the use of any other ester substituent. The selectivity and the product ratios are reported for o-fluoro-, o-chloro-, o-bromo-, and o-iodobenzoate esters (methyl, ethyl, n-propyl, allyl, and propargyl). Experimental and spectral data, as well as absolute stereochemistry, are provided for all new compounds.

  DOI：

  10.1021/op400343c