(7S,8S,R-biar)-6,7,8,9-tetrahydro-1,2,3,13,14-pentamethoxy-7,8-dimethyl-7,12-dibenzocyclooctenediol | 119139-66-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 单宁
• 英文名称: (7S,8S,R-biar)-6,7,8,9-tetrahydro-1,2,3,13,14-pentamethoxy-7,8-dimethyl-7,12-dibenzocyclooctenediol
• 英文别名: gomisin T；(9S,10S)-3,4,14,15,16-pentamethoxy-9,10-dimethyltricyclo[10.4.0.02,7]hexadeca-1(16),2,4,6,12,14-hexaene-5,10-diol
• CAS: 119139-66-1
• 化学式: C₂₃H₃₀O₇
• 分子量: 418.487
• InChiKey: LZUYISWUVHJQPR-MYODQAERSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  86.6
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (7S,8S,R-biar)-6,7,8,9-tetrahydro-1,2,3,13,14-pentamethoxy-7,8-dimethyl-7,12-dibenzocyclooctenediol 在 2,2,6,6-四甲基哌啶 、 三氯化硼 、 potassium carbonate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 25.5h， 生成 gomisin A
  参考文献：
  名称：

  Transformation of Schizandrin into Gomisin A by Use of MicrobialO-Demethylation and Chemical Reactions

  摘要：

  通过生物转化和化学反应相结合的方法，将五味子异黄酮（I）转化为戈米辛 A（II）。Cuntiinghamella echinulata var. elegans (ATCC 9245) 对 I 进行生物转化和微生物 O-去甲基化后，产生了两种新型代谢物[3-去甲五味子素（IV）和 2-去甲五味子素（VI）]和两种已知代谢物[五味子素 T（III）和 13-去甲五味子素（V）]。在这些代谢物中，化合物 III 是在有酸清除剂存在的情况下通过路易斯酸的 O-去甲基化反应生成 II 的，然后再进行甲基化反应。

  DOI：

  10.1271/bbb.58.1054
• 作为产物：
  描述：

  schizandrin 在 Mortierella sp. fungus 作用下， 以 水 为溶剂， 反应 336000.0h， 生成 (7S,8S,R-biar)-6,7,8,9-tetrahydro-1,2,3,13,14-pentamethoxy-7,8-dimethyl-7,12-dibenzocyclooctenediol
  参考文献：
  名称：

  Regio- and stereoselective 12-O-demethylation of schizandrin into gomisin T, an important intermediate to gomisin A, by Mortierella sp. (TM-I1104)

  摘要：

  A strain TM-11104 identified as Mortierella sp. was discovered from soil as the most efficient fungus, which converted schizandrin into gomisin T in 91% regioselectivity by microbial 12-O-demethylation. Under optimum conditions, the yield of gomisin T reached around 80%. The faculty of 12-O-demethylation was specific on (+)-schizandrin (natural form) and the optical purity of gomisin T converted from (+)-schizandrin was 96% ee. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.10.014

文献信息

• Ikeya, Yukinobu; Kanatani, Hirotoshi; Hakozaki, Misako, Chemical and pharmaceutical bulletin, 1988, vol. 36, # 10, p. 3974 - 3979
  作者：Ikeya, Yukinobu、Kanatani, Hirotoshi、Hakozaki, Misako、Taguchi, Heihachiro、Mitsuhashi, Hiroshi

  DOI：——

  日期：——
• IKEYA, YUKINOBU;KANATANI, HIROTOSHI;HAKOZAKI, MISAKO;TAGUCHI, HEIHACHIRO;+, CHEM. AND PHARM. BULL., 36,(1988) N 10, C. 3974-3979
  作者：IKEYA, YUKINOBU、KANATANI, HIROTOSHI、HAKOZAKI, MISAKO、TAGUCHI, HEIHACHIRO、+

  DOI：——

  日期：——
• Regio- and stereoselective 12-O-demethylation of schizandrin into gomisin T, an important intermediate to gomisin A, by Mortierella sp. (TM-I1104)
  作者：Hirotoshi Kanatani、Susumu Terabayashi、Shuichi Takeda、Wei Li、Kazuo Koike、Tamotsu Nikaido

  DOI：10.1016/j.tetlet.2005.10.014

  日期：2005.12

  A strain TM-11104 identified as Mortierella sp. was discovered from soil as the most efficient fungus, which converted schizandrin into gomisin T in 91% regioselectivity by microbial 12-O-demethylation. Under optimum conditions, the yield of gomisin T reached around 80%. The faculty of 12-O-demethylation was specific on (+)-schizandrin (natural form) and the optical purity of gomisin T converted from (+)-schizandrin was 96% ee. (c) 2005 Elsevier Ltd. All rights reserved.
• Transformation of Schizandrin into Gomisin A by Use of Microbial<i>O</i>-Demethylation and Chemical Reactions
  作者：Hirotoshi Kanatani、Chiaki Sakakibara、Masahide Tanaka、Kazuaki Niitsu、Yukinobu Ikeya、Takeshi Wakamatsu、Masao Maruno

  DOI：10.1271/bbb.58.1054

  日期：1994.1

  The transformation of schizandrin (I) into gomisin A (II) was accomplished by use of a combination of biotransformation and chemical reactions. The biotransformation, microbial O-demethylation of I by Cuntiinghamella echinulata var. elegans (ATCC 9245) produced two novel metabolites [3-norschizandrin (IV) and 2-norschizandrin (VI)] and two known metabolites [gomisin T (III) and 13-norschizandrin (V)]. Among those metabolites, compound III was derived to II by the O-demethylation with a Lewis acid in the presence of an acid scavenger, followed by methylenation.

  通过生物转化和化学反应相结合的方法，将五味子异黄酮（I）转化为戈米辛 A（II）。Cuntiinghamella echinulata var. elegans (ATCC 9245) 对 I 进行生物转化和微生物 O-去甲基化后，产生了两种新型代谢物[3-去甲五味子素（IV）和 2-去甲五味子素（VI）]和两种已知代谢物[五味子素 T（III）和 13-去甲五味子素（V）]。在这些代谢物中，化合物 III 是在有酸清除剂存在的情况下通过路易斯酸的 O-去甲基化反应生成 II 的，然后再进行甲基化反应。