(1R,2R,3R,4R)-anti-benzene dioxide | 80582-75-8

• 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: (1R,2R,3R,4R)-anti-benzene dioxide
• 英文别名: trans-benzene dioxide；(-)-anti-benzene 1,2:3,4-dioxide；anti-Benzoldioxid；anti-Benzene dioxide；(1R,2R,4R,7R)-3,8-dioxatricyclo[5.1.0.02,4]oct-5-ene
• CAS: 80582-75-8
• 化学式: C₆H₆O₂
• 分子量: 110.112
• InChiKey: LWOLJZRFQMSDAZ-KVTDHHQDSA-N

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：

  (1R,2R,3R,4R)-anti-benzene dioxide 以18%的产率得到
  参考文献：
  名称：

  Esser Thomas, Farkas Frederic, Mangholz Sissi, Sequin Urs, Tetrahedron, 50 (1994) N 12, S 3709-3720

  摘要：

  DOI：
• 作为产物：
  描述：

  (+)-(1R,2S,3S,4R)-2,3-dibromocyclohex-5-ene-1,4-diol 在 氢氧化钾 作用下， 以 四氢呋喃 为溶剂， 生成 (1R,2R,3R,4R)-anti-benzene dioxide
  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

文献信息

• Concerning the reaction of anti-benzene dioxide with various nucleophiles
  作者：Thomas Esser、Frédéric Farkas、Sissi Mangholz、Urs Séquin

  DOI：10.1016/s0040-4020(01)90392-8

  日期：1994.3

  6-Diepoxycyclohex-1-ene (anti-benzene dioxide) (5) was brought into reaction with several S, O, and C nucleophiles. S and O nucleophiles gave the bis-adducts stemming from independent reaction of the two epoxy functions. C nucleophiles, on the other hand, led to 1,4-addition products. A deuterium labelling experiment showed that BuLi added to the vinyloxirane part of 5 rather than to the conjugated diepoxide

  使反式-3,4：5,6-二环氧环己-1-烯（抗二氧化苯）（5）与几个S，O和C亲核试剂反应。S和O亲核试剂产生了由两个环氧官能团的独立反应产生的双加合物。另一方面，C亲核试剂产生1，4-加成产物。氘标记实验表明，BuLi添加到5的乙烯基环氧乙烷部分中，而不是添加到共轭二环氧官能团上，产生顺式加合物。像预期的那样，铜酸盐主要产生反式产物。
• Enantiopure arene dioxides: chemoenzymatic synthesis and application in the production of trans-3,4-dihydrodiols
  作者：Derek R. Boyd、Narain D. Sharma、Colin R. O’Dowd、Francis Hempenstall

  DOI：10.1039/b006837n

  日期：——

  Enantiopure syn- and anti-arene dioxides are synthesised from cis-dihydrodiol metabolites; anti-benzene dioxides are reduced to enantiopure trans-3,4-dihydrodiols while syn-benzene dioxides racemise thermally via 1,4-dioxocins.

  对映纯的顺式和反式芳烃二氧化物是从顺式二氢二醇代谢物合成的；反式苯二氧化物被还原为对映纯的反式-3,4-二氢二醇，而顺式苯二氧化物则通过1,4-二氧烯在热条件下发生消旋。
• 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。
• Mueller, Klaus-Helmut; Kaiser, Clemens; Pillat, Michael, Chemische Berichte, 1983, vol. 116, # 7, p. 2492 - 2523
  作者：Mueller, Klaus-Helmut、Kaiser, Clemens、Pillat, Michael、Zipperer, Bernhard、Froom, Manfred、et al.

  DOI：——

  日期：——
• 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.