(+)-顺式-2(r),3(s)-2,3-二羟基-2,3-二氢苯甲腈丙酮化合物 | 150767-96-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: (+)-顺式-2(r),3(s)-2,3-二羟基-2,3-二氢苯甲腈丙酮化合物
• 英文名称: (3aS,7aS)-2,2-dimethyl-3a,7a-dihydro-1,3-benzodioxole-4-carbonitrile
• 英文别名: (1R,6S)-2-cyano-8,8-dimethyl-7,9-dioxabicyclo<4.3.0>nona-2,4-diene；(+)-cis-2(R),3(S)-2,3-Dihydroxy-2,3-dihydrobenzonitrile acetonide；(3aR,7aS)-2,2-dimethyl-3a,7a-dihydro-1,3-benzodioxole-4-carbonitrile
• CAS: 150767-96-7
• 化学式: C₁₀H₁₁NO₂
• 分子量: 177.203
• InChiKey: MXAWGNNBDOUVJD-DTWKUNHWSA-N

物化性质

• 沸点：
  294.6±40.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  42.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+)-顺式-2(r),3(s)-2,3-二羟基-2,3-二氢苯甲腈丙酮化合物 在 sodium chlorite 、 sodium tetrahydroborate 、 四氧化锇 、 N-甲基吲哚酮 、 NaH₂PO₄ buffer 、 二异丁基氢化铝 、 丙酮 、 三氟乙酸 作用下， 以 乙醚 、 水 、 丙酮 、 叔丁醇 为溶剂， 反应 110.0h， 生成 (1R,4R,8R,9R)-2-hydroxymethyl-6,6,11,11-tetramethyl-5,7,10,12-tetraoxabicyclo<7.3.0.0^9,1>dodec-2-ene
  参考文献：
  名称：

  Enantiospecific synthesis of cyanocyclitols and (6R)-6-hydroxyshikimic acid from benzonitrile

  摘要：

  The chiral cis-3-cyanocyclohexa-3,5-diene-1,2-diol 5. available by microbial oxidation of benzonitrile, is the key intermediate used in brief syntheses of the cyanocyclitols 9 and 15, and in the synthesis of 6-hydroxyshikimic acid 20. (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00055-9
• 作为产物：
  描述：

  苯甲腈 在 ammonium hydroxide 、 对甲苯磺酸 作用下， 以 丙酮 、 paraffin oil 为溶剂， 生成 (+)-顺式-2(r),3(s)-2,3-二羟基-2,3-二氢苯甲腈丙酮化合物
  参考文献：
  名称：

  Aza and oxo Diels–Alder reactions using cis-cyclohexadienediols of microbial origin: chemoenzymatic preparation of synthetically valuable heterocyclic scaffolds

  摘要：

  Aza and oxo Diels-Alder reactions using enantiopure cis-cyclohexadienediols were studied. These dienediols were obtained from the biotransformation of monosubstituted arenes using bacterial dioxygenases (toluene and benzoate dioxygenases). Ethyl glyoxylate and its N-tosyl imine were used as dienophiles to afford the corresponding hetero Diels-Alder bicyclic adducts with excellent regio- and stereoselectivities. Quantum chemical calculations at the B3LYP/6-31+G(d,p) level of theory were performed to rationalize the observed selectivities especially the stereochemical aspects of the cycloadditions. The synthetic importance of these adducts is highlighted for the preparation of enantiopure 2,2,3,4,5,6-hexasubstituted piperidine and tetrahydropyran from toluene. (c) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2015.10.015

文献信息

• Blacker, A. John; Booth, R. John; Davies, Gareth M., Journal of the Chemical Society. Perkin transactions I, 1995, # 22, p. 2861 - 2870
  作者：Blacker, A. John、Booth, R. John、Davies, Gareth M.、Sutherland, James K.

  DOI：——

  日期：——
• Synthesis of (−)-6-hydroxyshikimic acid from ((5S,6R)-5,6-dihydroxy-1,3-cyclohexadienyl)methanenitrile
  作者：Chuong Hao Tran、David H.G. Crout、William Errington、Gregory M. Whited

  DOI：10.1016/0957-4166(96)00064-x

  日期：1996.3
• Aza and oxo Diels–Alder reactions using cis-cyclohexadienediols of microbial origin: chemoenzymatic preparation of synthetically valuable heterocyclic scaffolds
  作者：Mariana Pazos、Sebastián Martínez、María Agustina Vila、Paola Rodríguez、Nicolás Veiga、Gustavo Seoane、Ignacio Carrera

  DOI：10.1016/j.tetasy.2015.10.015

  日期：2015.12

  Aza and oxo Diels-Alder reactions using enantiopure cis-cyclohexadienediols were studied. These dienediols were obtained from the biotransformation of monosubstituted arenes using bacterial dioxygenases (toluene and benzoate dioxygenases). Ethyl glyoxylate and its N-tosyl imine were used as dienophiles to afford the corresponding hetero Diels-Alder bicyclic adducts with excellent regio- and stereoselectivities. Quantum chemical calculations at the B3LYP/6-31+G(d,p) level of theory were performed to rationalize the observed selectivities especially the stereochemical aspects of the cycloadditions. The synthetic importance of these adducts is highlighted for the preparation of enantiopure 2,2,3,4,5,6-hexasubstituted piperidine and tetrahydropyran from toluene. (c) 2015 Elsevier Ltd. All rights reserved.
• Enantiospecific synthesis of cyanocyclitols and (6R)-6-hydroxyshikimic acid from benzonitrile
  作者：Howard A.J. Carless、Yvonne Dove

  DOI：10.1016/0957-4166(96)00055-9

  日期：1996.3

  The chiral cis-3-cyanocyclohexa-3,5-diene-1,2-diol 5. available by microbial oxidation of benzonitrile, is the key intermediate used in brief syntheses of the cyanocyclitols 9 and 15, and in the synthesis of 6-hydroxyshikimic acid 20. (C) 1996 Elsevier Science Ltd