(3S,4S)-methyl 2-chloro-3,4-dihydroxycyclohexa-1,5-dienecarboxylate | 1380226-09-4

• 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: (3S,4S)-methyl 2-chloro-3,4-dihydroxycyclohexa-1,5-dienecarboxylate
• 英文别名: methyl (5S,6R)-2-chloro-5,6-dihydroxycyclohexa-1,3-diene-1-carboxylate
• CAS: 1380226-09-4
• 化学式: C₈H₉ClO₄
• 分子量: 204.61
• InChiKey: YNNLYMDWHKEJDI-FSPLSTOPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3S,4S)-methyl 2-chloro-3,4-dihydroxycyclohexa-1,5-dienecarboxylate 在 potassium diazodicarboxylate 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 14.0h， 生成 methyl (5S,6R)-5,6-dihydroxy-2-chlorocyclohex-1-enecarboxylate
  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
• 作为产物：
  描述：

  2-氯苯甲酸甲酯 在 Escherichia coli JM₁₀₉ (pDTG₆₀₁A) 作用下， 生成 (3S,4S)-methyl 2-chloro-3,4-dihydroxycyclohexa-1,5-dienecarboxylate
  参考文献：
  名称：

  Toluene dioxygenase mediated oxidation of halogen-substituted benzoate esters

  摘要：

  一系列邻、间和对卤代甲基苯甲酸酯通过全细胞发酵与大肠杆菌JM109（pDTG601A）发生酶促二羟基化反应。只有邻取代的苯甲酸酯被代谢。2-氟苯甲酸甲酯产生一种二醇，而2-氯、2-溴和2-碘苯甲酸甲酯则分别产生一种区域异构体混合物。所有新代谢产物的绝对立体化学结构均已确定。对这些结果进行了计算分析，并提出了酶促二羟基化反应区域选择性的可能原理。

  DOI：

  10.1039/c2ob25202c