(+)-(1S,2S)-1,2-dihydroxy-1,2-dihydrobenzene | 103364-68-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (+)-(1S,2S)-1,2-dihydroxy-1,2-dihydrobenzene
• 英文别名: (S,S)-(+)-3,5-cyclohexadiene-1,2-diol；(S,S)-3,5-cyclohexadiene-1,2-diol；trans-5,6-Dihydroxy-cyclohexadien-(1,3)；trans-1,2-Dihydroxy-1,2-dihydrobenzol；trans-Benzolglykol；(1S,2S)-cyclohexa-3,5-diene-1,2-diol
• CAS: 103364-68-7
• 化学式: C₆H₈O₂
• 分子量: 112.128
• InChiKey: YDRSQRPHLBEPTP-WDSKDSINSA-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：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (+)-(1S,2S)-1,2-dihydroxy-1,2-dihydrobenzene 在 disodium hydrogenphosphate 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.75h， 以67%的产率得到(+)-(1S,2R,3S,6R)-7-oxabicyclo<4.1.0>hept-4-ene-2,3-diol
  参考文献：
  名称：

  Resolution of trans-1,2-dihydroxy-1,2-dihydrobenzene for the preparation of optically pure benzene diol epoxides. Preparation of bromo- and chlorobenzene diol epoxides

  摘要：

  DOI：

  10.1021/jo00273a005
• 作为产物：
  描述：

  trans-1,3-Cyclohexadien-5,6-diyldiacetat 在 sodium hydroxide 、 水 作用下， 反应 46.0h， 生成 (+)-(1S,2S)-1,2-dihydroxy-1,2-dihydrobenzene
  参考文献：
  名称：

  Resolution of trans-1,2-dihydroxy-1,2-dihydrobenzene for the preparation of optically pure benzene diol epoxides. Preparation of bromo- and chlorobenzene diol epoxides

  摘要：

  DOI：

  10.1021/jo00273a005

文献信息

• GANEY, MICHAEL V.;PADYKULA, ROBERT E.;BERCHTOLD, GLENN A.;BRAUN, ANDREW G+, J. ORG. CHEM., 54,(1989) N2, C. 2787-2793
  作者：GANEY, MICHAEL V.、PADYKULA, ROBERT E.、BERCHTOLD, GLENN A.、BRAUN, ANDREW G+

  DOI：——

  日期：——
• Enzymatic characterization of a novel bovine liver dihydrodiol dehydrogenase - reaction mechanism and bile acid dehydrogenase activity
  作者：Hirofumi Nanjo、Hideki Adachi、Shoko Morihana、Tadashi Mizoguchi、Tsutomu Nishihara、Tomoyuki Terada

  DOI：10.1016/0304-4165(94)00195-4

  日期：1995.5

  Bovine liver cytosolic dihydrodiol dehydrogenase (DD3) has been characterized by its unique dihydrodiol dehydrogenase activity for trans-benzenedihydrodiol (trans-1,2-dihydrobenzene-1,2-diol) with the highest affinity and the greatest velocity among three multiple forms of dihydrodiol dehydrogenases (DD1-DD3). It is the first time that DD3 has shown a significant dehydrogenase activity for (S)-(+)-1-indanol with low K-m value (0.33 +/- 0.022 mM) and high K-cat value (25 +/- 0.79 min(-1)). The investigation of the product inhibition of (S)-(+)-1-indanol with NADP(+) versus 1-indanone and NADPH clearly showed that the enzymatic reaction of DD3 may follow a typical ordered Bi Bi mechanism similar to many aldo/keto reductases. Additionally, DD3 was shown to catalyze the dehydrogenation of bile acids (lithocholic acid, taurolithocholic acid anti taurochenodeoxycholic acid) having no 12-hydroxy groups with low K-m values (17 +/- 0.65, 33 +/- 1.9 and 890 +/- 73 mu M, respectively). In contrast, DD1, 3 alpha-hydroxysteroid dehydrogenase, shows a broad substrate specificity for many bile acids with higher affinity than those of DD3. Competitive inhibition of DD3 with androsterone against dehydrogenase activity for (S)-(+)-1-indanol, trans-benzenedihydrodiol or lithocholic acid suggests that these three substrates bind to the same substrate binding site of DD3, different from the case of human liver bile acid binder/dihydrodiol dehydrogenase (Takikawa, H., Stolz, A., Sugiyama, Y., Yoshida, H., Yamamoto, M. and Kaplowitz, N. (1990) J. Biol. Chem. 265, 2132-2136). Considering the reaction mechanism, DD3 may also play an important role in bile acids metabolism as well as the detoxication of aromatic hydrocarbons.
• Enzymic aromatization of 3,5-cyclohexadiene-1,2-diol
  作者：Padmadini K. Ayengar、Osamu Hayaishi、Minoru Nakajima、Ichiro Tomida

  DOI：10.1016/0006-3002(59)90504-9

  日期：1959.5
• US4855512A
  申请人：——

  公开号：US4855512A

  公开（公告）日：1989-08-08
• Resolution of trans-1,2-dihydroxy-1,2-dihydrobenzene for the preparation of optically pure benzene diol epoxides. Preparation of bromo- and chlorobenzene diol epoxides
  作者：Michael V. Ganey、Robert E. Padykula、Glenn A. Berchtold、Andrew G. Braun

  DOI：10.1021/jo00273a005

  日期：1989.6