(3aS,4S,5S,7aS)-7-bromo-5-fluoro-2,2-dimethyl-4,5-dihydrobenzo<1,3>dioxol-4-ol | 192448-72-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3aS,4S,5S,7aS)-7-bromo-5-fluoro-2,2-dimethyl-4,5-dihydrobenzo<1,3>dioxol-4-ol
• 英文别名: (3aS,4S,5S,7aS)-7-bromo-5-fluoro-2,2-dimethyl-3a,4,5,7a-tetrahydro-1,3-benzodioxol-4-ol
• CAS: 192448-72-9
• 化学式: C₉H₁₂BrFO₃
• 分子量: 267.095
• InChiKey: PBHOCJHNNWOKCJ-OSMVPFSASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3aS,4S,5S,7aS)-7-bromo-5-fluoro-2,2-dimethyl-4,5-dihydrobenzo<1,3>dioxol-4-ol 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 苯 为溶剂， 以95%的产率得到(3aS,4S,5S,7aR)-2,2-dimethyl-5-fluoro-3a,4,5,7a-tetrahydro-1,3-benzodioxol-4-ol
  参考文献：
  名称：

  Chemoenzymatic enantiodivergent synthesis of 1,2-dideoxy-2-amino-1-fluoro-allo-inositol

  摘要：

  Both enantiomers of dideoxyfluoroamino inositols (+)-9 and (-)-9 were synthesized from bromocyclohexadiene cis-diol 1 obtained by microbial oxidation of bromobenzene with toluene dioxygenase. Selective introduction of the amino group was achieved through S(N)2 displacement of triflates 7, 11. Fluorine was selectively introduced via trans-diaxial epoxide opening with tetrabutylphosphonium fluoride dihydrofluoride (TBPF-DF). (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00080-0
• 作为产物：
  描述：

  [3aS-(3aα,5aβ,6aβ,6bα)]-4-溴-3a,5a,6a,6b-四氢-2,2-二甲基环氧乙烷并[e]-1,3-苯并二茂 在 TBPF-DF 作用下， 反应 576.0h， 以79%的产率得到(3aS,4S,5S,7aS)-7-bromo-5-fluoro-2,2-dimethyl-4,5-dihydrobenzo<1,3>dioxol-4-ol
  参考文献：
  名称：

  Chemoenzymatic synthesis of deoxyfluoroinositols: 5-deoxy-5-fluoro-myo-inositol and 3-deoxy-3-fluoro-L-chiro-inositol

  摘要：

  DOI：

  10.1016/s0040-4020(97)90392-6

文献信息

• Chemoenzymatic synthesis of fluorinated carbohydrates: 2-Deoxy-2-fluoro-d-glucose and 5-deoxy-5-fluoro-manno-γ-lactol
  作者：Fengyang Yan、Ba V. Nguyen、Chentao York、Tomas Hudlicky

  DOI：10.1016/s0040-4020(97)00746-1

  日期：1997.8

  Two fluorinated hexoses were prepared from optically active cis-diols 1, which were obtained by microbial oxidation of the corresponding halobenzenes with E. coli JM109 (pDTG 601). The stereochemistry of the products was controlled by careful introduction of fluorine onto the periphery of the cis-diols via opening of epoxides with tetrabutylphosphoniumfluoride dihydrofluoride (TBPF-DF). Oxidative cleavage

  由旋光性顺式-二醇1制备了两种氟化己糖，它们是通过用大肠杆菌JM109（pDTG 601）对相应的卤代苯进行微生物氧化而获得的。通过用四丁基氟化was二氢氟化物（TBPF-DF）打开环氧化物，小心地将氟引入顺式二醇的周边，从而控制产物的立体化学。环己烯骨架的氧化裂解，然后还原环化导致氟化己糖。
• Hudlicky, Tomas; Luna, Hector; Olivo, Horacio F., Journal of the Chemical Society. Perkin transactions I, 1991, # 12, p. 2907 - 2918
  作者：Hudlicky, Tomas、Luna, Hector、Olivo, Horacio F.、Andersen, Catherine、Nugent, Thomas、Price, John D.

  DOI：——

  日期：——