(3S,5S)-3,5-dihydroxy-1,7-bis(3,4,5-trimethoxyphenyl)heptane | 1346752-72-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: (3S,5S)-3,5-dihydroxy-1,7-bis(3,4,5-trimethoxyphenyl)heptane
• 英文别名: (3S,5S)-1,7-bis(3,4,5-trimethoxyphenyl)heptane-3,5-diol
• CAS: 1346752-72-4
• 化学式: C₂₅H₃₆O₈
• 分子量: 464.556
• InChiKey: ACOSQSKPYYYRMJ-OALUTQOASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  33
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  95.8
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (3S,5S)-3,5-dihydroxy-1,7-bis(3,4,5-trimethoxyphenyl)heptane 、 4-溴苯甲酰氯 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以64%的产率得到(3S,5S)-3,5-di(4-bromobenzoyloxy)-1,7-bis(3,4,5-trimethoxyphenyl)heptane
  参考文献：
  名称：

  A new diarylheptanoid from the rhizomes of Zingiber mekongense

  摘要：

  A new diarylheptanoid, (3S,5S)-3,5-diacetoxy-1,7-bis(3,4,5-trimethoxyphenyl)heptane (1), together with the known docosyl trans-ferulate (2), (1S,2S,4S)-p-menthan-1,2,4-triol (3), 5 alpha H-eudesmane-4 alpha,11-diol (4), 5 alpha H-eudesmane-4 beta,11-diol (5), 4 alpha, 10 beta-dihydroxy-1 beta H,5 alpha H-guaia-6-ene (guaianediol) (6), (+)-galanolactone (7), (E)-labda-8(17),12(13)-dien-15,16-olide (8), labda-8(17),13(14)-dien-15,16-olide (9), 3,5-dihydroxy-7,4'-dimethoxyflavone (10) and 3,5,3'-trihydroxy-7.4'-dimethoxyflavone (11) were isolated from the rhizomes of Zingiber mekongense. Their structures were determined by spectroscopic methods. The stereochemistry of 1 was proved through chemical conversion. Compounds 1,4-7 and 9-11 exhibited anti-HIV-1 activities in the anti-syncytium assay using (Delta Tat/rev)MC99 virus and 1A2 cell line system, while only compounds 7 and 11 were found active in the HIV-1 reverse transcriptase assay. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.fitote.2011.01.002
• 作为产物：
  描述：

  3-(3,4,5-三甲氧基苯基)-1-丙醇 在 2,6-二甲基吡啶 、 正丁基锂 、 四丁基氟化铵 、 氢气 、 palladium(II) hydroxide 、 四氯化钛 、 二异丁基氢化铝 、 溶剂黄146 、 二甲基亚砜 、 N,N-二异丙基乙胺 、 tetramethylammonium triacetoxyborohydride 、 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 甲苯 、 乙腈 、 苯 为溶剂， 反应 25.08h， 生成 (3S,5S)-3,5-dihydroxy-1,7-bis(3,4,5-trimethoxyphenyl)heptane
  参考文献：
  名称：

  Synthesis of gingerol and diarylheptanoids

  摘要：

  The synthesis of gingerol 1 and related compounds 2-5 along with diarylheptanoids 6-8 has been accomplished using a Keck allylation, Crimmins' aldol reaction, aldehyde coupling with acetylene, and chelation controlled reductions as the key reactions. The absolute configuration of these molecules was confirmed by preparing their acetonide derivatives and by comparison of the NMR data with natural compounds. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.11.010

文献信息

• Synthesis of gingerol and diarylheptanoids
  作者：Gowravaram Sabitha、Chitti Srinivas、Teega Rammohan Reddy、Kurra Yadagiri、Jhillu Singh Yadav

  DOI：10.1016/j.tetasy.2011.11.010

  日期：2011.12

  The synthesis of gingerol 1 and related compounds 2-5 along with diarylheptanoids 6-8 has been accomplished using a Keck allylation, Crimmins' aldol reaction, aldehyde coupling with acetylene, and chelation controlled reductions as the key reactions. The absolute configuration of these molecules was confirmed by preparing their acetonide derivatives and by comparison of the NMR data with natural compounds. (C) 2011 Elsevier Ltd. All rights reserved.
• A new diarylheptanoid from the rhizomes of Zingiber mekongense
  作者：Arthittaya Chareonkla、Manat Pohmakotr、Vichai Reutrakul、Chalobon Yoosook、Jitra Kasisit、Chanita Napaswad、Patoomratana Tuchinda

  DOI：10.1016/j.fitote.2011.01.002

  日期：2011.6

  A new diarylheptanoid, (3S,5S)-3,5-diacetoxy-1,7-bis(3,4,5-trimethoxyphenyl)heptane (1), together with the known docosyl trans-ferulate (2), (1S,2S,4S)-p-menthan-1,2,4-triol (3), 5 alpha H-eudesmane-4 alpha,11-diol (4), 5 alpha H-eudesmane-4 beta,11-diol (5), 4 alpha, 10 beta-dihydroxy-1 beta H,5 alpha H-guaia-6-ene (guaianediol) (6), (+)-galanolactone (7), (E)-labda-8(17),12(13)-dien-15,16-olide (8), labda-8(17),13(14)-dien-15,16-olide (9), 3,5-dihydroxy-7,4'-dimethoxyflavone (10) and 3,5,3'-trihydroxy-7.4'-dimethoxyflavone (11) were isolated from the rhizomes of Zingiber mekongense. Their structures were determined by spectroscopic methods. The stereochemistry of 1 was proved through chemical conversion. Compounds 1,4-7 and 9-11 exhibited anti-HIV-1 activities in the anti-syncytium assay using (Delta Tat/rev)MC99 virus and 1A2 cell line system, while only compounds 7 and 11 were found active in the HIV-1 reverse transcriptase assay. (C) 2011 Elsevier B.V. All rights reserved.