(1S,2S,3S,4S)-anti-benzene dioxide | 80582-74-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环氧化物
• 英文名称: (1S,2S,3S,4S)-anti-benzene dioxide
• 英文别名: (+)-anti-benzene 1,2:3,4-dioxide；(1S,2S,4S,7S)-3,8-dioxatricyclo[5.1.0.02,4]oct-5-ene
• CAS: 80582-74-7
• 化学式: C₆H₆O₂
• 分子量: 110.112
• InChiKey: LWOLJZRFQMSDAZ-BXKVDMCESA-N

物化性质

• 熔点：
  53 °C
• 沸点：
  179.0±33.0 °C(Predicted)
• 密度：
  1.387±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  25.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1S,2S,3S,4S)-anti-benzene dioxide 在 palladium on activated charcoal 吡啶 、 四氮唑 、 ruthenium trichloride 、 sodium hydroxide 、 sodium periodate 、 InsP₄-phosphohydrolase 、 氢气 、 间氯过氧苯甲酸 作用下， 以 水 为溶剂， 生成 Inositol 1,2,3-triphosphate
  参考文献：
  名称：

  De novo synthesis of the enantiomers Ins(1,2,3,4)P4 and Ins(1,2,3,6)P4—regiospecificity of their enzymatic dephosphorylation

  摘要：

  (T)he first total synthesis of Ins(1,2,3,4)P-4 and Ins(1,2,3,6)P-4 is presented. Starting from p-benzoquinone, we took advantage of the C-2-symmetry of conduritol-B intermediates. The target compounds were dephosphorylated by several enzymes, and the resulting InsP(3) isomers, were identified. Some of these enzymatic conversions were found to be preparatively applicable and to allow the synthesis of Ins(1,2,3)P-3, Ins(2,3,6)P-3 and Ins(1,2,4)P-3. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00063-x
• 作为产物：
  描述：

  (+)-(1S,2R,3R,4S)-1,4-diacetoxy-2,3-dibromocyclohex-5-ene 在 氢氧化钾 、 4 A molecular sieve 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 1.0h， 以80%的产率得到(1S,2S,3S,4S)-anti-benzene dioxide
  参考文献：
  名称：

  Enzyme-Assisted Total Synthesis of the Optical Antipodes d-myo-Inositol 3,4,5-Trisphosphate and d-myo-Inositol 1,5,6-Trisphosphate:  Aspects of Their Structure−Activity Relationship to Biologically Active Inositol Phosphates

  摘要：

  Unambiguous total syntheses of bath optical antipodes of the enantiomeric pair D-myo-inositol 3,4,5-trisphosphate (Ins(3,4,5)P-3) and D-myo-inositol 1,5,6-trisphosphate (Ins(1,5,6)P-3) are described. The ring system characteristic of myo-inositol was constructed de novo from p-benzoquinone. X-ray data for the enzymatically resolved (1S,2R,3R,4S)-1,4-diacetoxy-2,3-dibromocyclohex-5-ene enabled the unequivocal assignment of the absolute configuration. Subsequent transformations under stereocontrolled conditions led to enantiopure C-2-symmetrical 1,4-(di-O-benzyldiphospho)conduritol B derivatives. Their synthetic potential was exploited to prepare Ins(3,4,5,6)P-4 and Ins(1,4,5,6)P-4 in three steps. With a recently identified and partially purified InsP(5)/InsP(4) phosphohydrolase from Dictyostelium discoideum, these enantiomers could be converted to the target compounds, Ins(3,4,5)P-3 and Ins(1,5,6)P-3, on a preparative scale. An HPLC system employed for both purification of the inositol phosphates and analytical runs ensured that the products were isomerically homogeneous. The sensitivity of detection achieved by a complexometric postcolumn derivatization method indicates that the complexation properties of Ins(3,4,5)P-3/Ins(1,5,6)P-3 resemble those of Ins(1,2,3)P-3, a compound with antioxidantpotential. The set of inositol phosphates synthesized was used to clarify structural motifs important for molecular recognition by p42(IP4) , high-affinity Ins(1,3,4,5)P-4/PtdIns(3,4,5)P-3-specific binding protein from pig cerebellum.

  DOI：

  10.1021/jm981113k

文献信息

• The absolute configurations of anti-benzene and anti-naphthalene 1,2:3,4-dioxides
  作者：Masato Koreeda、Minoru Yoshihara

  DOI：10.1039/c39810000974

  日期：——

  Optically active anti-1,2 : 3,4-dioxides of benzene and naphthalene have been synthesized and their absolute configurations assigned using the exciton chirality c.d. method.

  已经合成了苯和萘的光学活性抗-1,2：3,4-二氧化物，并使用激子手性cd方法确定了它们的绝对构型。
• Enzyme-Assisted Total Synthesis of the Optical Antipodes <scp>d</scp>-<i>myo</i>-Inositol 3,4,5-Trisphosphate and <scp>d</scp>-<i>myo</i>-Inositol 1,5,6-Trisphosphate:  Aspects of Their Structure−Activity Relationship to Biologically Active Inositol Phosphates
  作者：Stephan Adelt、Oliver Plettenburg、Rolf Stricker、Georg Reiser、Hans-Josef Altenbach、Günter Vogel

  DOI：10.1021/jm981113k

  日期：1999.4.1

  Unambiguous total syntheses of bath optical antipodes of the enantiomeric pair D-myo-inositol 3,4,5-trisphosphate (Ins(3,4,5)P-3) and D-myo-inositol 1,5,6-trisphosphate (Ins(1,5,6)P-3) are described. The ring system characteristic of myo-inositol was constructed de novo from p-benzoquinone. X-ray data for the enzymatically resolved (1S,2R,3R,4S)-1,4-diacetoxy-2,3-dibromocyclohex-5-ene enabled the unequivocal assignment of the absolute configuration. Subsequent transformations under stereocontrolled conditions led to enantiopure C-2-symmetrical 1,4-(di-O-benzyldiphospho)conduritol B derivatives. Their synthetic potential was exploited to prepare Ins(3,4,5,6)P-4 and Ins(1,4,5,6)P-4 in three steps. With a recently identified and partially purified InsP(5)/InsP(4) phosphohydrolase from Dictyostelium discoideum, these enantiomers could be converted to the target compounds, Ins(3,4,5)P-3 and Ins(1,5,6)P-3, on a preparative scale. An HPLC system employed for both purification of the inositol phosphates and analytical runs ensured that the products were isomerically homogeneous. The sensitivity of detection achieved by a complexometric postcolumn derivatization method indicates that the complexation properties of Ins(3,4,5)P-3/Ins(1,5,6)P-3 resemble those of Ins(1,2,3)P-3, a compound with antioxidantpotential. The set of inositol phosphates synthesized was used to clarify structural motifs important for molecular recognition by p42(IP4) , high-affinity Ins(1,3,4,5)P-4/PtdIns(3,4,5)P-3-specific binding protein from pig cerebellum.
• De novo synthesis of the enantiomers Ins(1,2,3,4)P4 and Ins(1,2,3,6)P4—regiospecificity of their enzymatic dephosphorylation
  作者：O Plettenburg、S Adelt、G Vogel、H.-J Altenbach

  DOI：10.1016/s0957-4166(00)00063-x

  日期：2000.3

  (T)he first total synthesis of Ins(1,2,3,4)P-4 and Ins(1,2,3,6)P-4 is presented. Starting from p-benzoquinone, we took advantage of the C-2-symmetry of conduritol-B intermediates. The target compounds were dephosphorylated by several enzymes, and the resulting InsP(3) isomers, were identified. Some of these enzymatic conversions were found to be preparatively applicable and to allow the synthesis of Ins(1,2,3)P-3, Ins(2,3,6)P-3 and Ins(1,2,4)P-3. (C) 2000 Elsevier Science Ltd. All rights reserved.