哥纳香三醇 | 96405-62-8

• 物质功能分类: 天然产物 - 酚类
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 中文名称: 哥纳香三醇
• 英文名称: (5S,6R)-6-[(1S,2R)-1-(benzyloxy)-1,2-dihydroxy-2-phenylethyl]-5-hydroxy-5,6-dihydro-2H-pyran-2-one
• 英文别名: (5S,6R,7R,8R)-goniotriol；(+)-goniotriol；goniotriol；(2R,3S)-2-[(1R,2R)-1,2-dihydroxy-2-phenylethyl]-3-hydroxy-2,3-dihydropyran-6-one
• CAS: 96405-62-8
• 化学式: C₁₃H₁₄O₅
• 分子量: 250.251
• InChiKey: AWCDBKHWVKLXEE-WKSBVSIWSA-N

物化性质

• 熔点：
  169-171 °C(Solv: hexane (110-54-3); ethanol (64-17-5))
• 沸点：
  554.8±50.0 °C(Predicted)
• 密度：
  1.419±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  87
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  哥纳香三醇 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 为溶剂， 反应 10.0h， 以60%的产率得到(+)-goniofufurone
  参考文献：
  名称：

  立体控制合成新型苯乙烯基内酯，（+）-goniodiol，（+）-goniotriol，（+）-8-乙酰基goniotriol，（+）-goniofufurone，（+）-9-deoxygoniopypyrone，（+）-goniopypyrone和（+ ）-内酯的常见中间体及其同系物的细胞毒性

  摘要：

  简捷合成（+）-goniodiol，（+）-goniotriol，（+）-8-乙酰基goniotriol，（+）-goniofufurone，（+）-9-脱氧goniopypyrone，（+）-goniopypyrone和（+）-邻甲内酯描述了它们来自手性内酯醛27和36的同类物，作为常见的中间体。合成中的关键特征是基于原位生成不稳定的醛27和36，然后它们与三异丙氧基苯基钛发生化学选择性反应，从而在C-8位提供非对映异构体28、29和37、38。检查了苯乙烯基内酯同源物对P388鼠白血病细胞的细胞毒性。

  DOI：

  10.1016/s0040-4020(99)00023-x
• 作为产物：
  描述：

  (4R,5R)-2,2-Dimethyl-5-phenyl-[1,3]dioxolane-4-carbaldehyde 在 chromium(VI) oxide 、 叔丁基过氧化氢 、 正丁基锂 、 bis(acetylacetonate)oxovanadium 、 三乙酰氧基硼氢化钠 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 19.25h， 生成 哥纳香三醇
  参考文献：
  名称：

  Asymmetric total synthesis of (+)-goniotriol and (+)-goniofufurone

  摘要：

  The Enantioselective synthesis of two antitumor styryl lactones, (+)-goniotriol and (+)-goniofufurone, have been completed starting from cinnamyl alcohol in ten and eleven steps with an overall yield of 21% and 12%, respectively.

  DOI：

  10.1016/0040-4020(94)01025-u

文献信息

• Stereoselective Synthesis of (+)-Goniodiol, (+)-Goniotriol, (-)-Goniofupyrone, and (+)-Altholactone Using a Catalytic Asymmetric Hetero-Diels-Alder/Allylboration Approach
  作者：Annaïck Favre、François Carreaux、Michael Deligny、Bertrand Carboni

  DOI：10.1002/ejoc.200800535

  日期：2008.10

  The stereoselective total synthesis of several members of the styryllactone family was achieved efficiently from common intermediate 8, prepared by a catalytic asymmetric inverse-electron-demand hetero-Diels–Alder/allylboration sequence. The transformation of 8 into α,β-unsaturated lactone led to the preparation of (+)-goniodiol (1) in a reduced number of steps. The epoxidation reaction was used to

  苯乙烯内酯家族的几个成员的立体选择性全合成是从普通中间体 8 有效地实现的，中间体 8 通过催化不对称逆电子需求异质狄尔斯-阿尔德/烯丙基硼化序列制备。将 8 转化为 α,β-不饱和内酯导致以减少的步骤数制备 (+)-goniodiol (1)。环氧化反应用于在 8 的内酯部分产生剩余的立体中心，然后将这些中间体加工成 (+)-goniotriol (2)、(-)-goniofupyrone (3) 和 (+)-altholactone ( 4) 通过异构化或环化步骤。 (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)
• Total synthesis of antitumor Goniothalamus styryllactones
  作者：Jean-Philippe Surivet、Jean-Michel Vatèle

  DOI：10.1016/s0040-4020(99)00794-2

  日期：1999.11

  synthesized via an efficient coupling between the primary triflate derived from the common intermediate 16 or its epimer and Ghosez's sulfone 11 followed by lactonization and PhSO2H elimination. Goniodiol 1 has been efficiently converted to another styryllactone: isogoniothalamin epoxide 41. Addition of the Ghosez's sulfone to an epoxide derived from the enantiomer of 16 allowed a short synthesis of 8-epi-

  从一个常见的前体即可合成八种对映体纯的苯乙烯基内酯：乙基（2 S，3 S，4 R）-4-（叔丁基二甲基甲硅烷氧基）-2,3-异丙基二烯二氧基-4-苯基丁酸酯16和65 （R）-扁桃酸的％收率。Z-丙烯酸酯部分通过16之间的Julia偶联引入Z-丙烯酸酯部分来合成goniofufurone 3，goniopypyrone 4，goniobutenolides A和B（5、6）和7- epi- goniofufurone 7的关键元素。或其在苄基位置的差向异构体和3-苯基磺酰基原丙酸甲酯11，然后高度非对映选择性还原所得的β-酮砜，从而建立了四个连续的不对称中心中的最后一个。在苯乙烯基内酯4和7的情况下，在Julia偶联之前，通过Mitsunobu反应有效地反转了16的苄基立体中心。通过从常见中间体16或其差向异构体衍生的伯三氟甲磺酸酯与Ghosez砜11进行有效偶联，然后进行内酯化和PhSO
• Stereocontrolled syntheses of novel styryl lactones, (+)-goniodiol, (+)-goniotriol, (+)-8-acetylgoniotriol, (+)-goniofufurone, (+)-9-deoxygoniopypyrone, (+)-goniopypyrone, and (+)-altholactone from common intermediates and cytotoxicity of their congeners
  作者：Masayoshi Tsubuki、Kazuo Kanai、Hiromasa Nagase、Toshio Honda

  DOI：10.1016/s0040-4020(99)00023-x

  日期：1999.2

  Concise syntheses of (+)-goniodiol, (+)-goniotriol, (+)-8-acetylgoniotriol, (+)-goniofufurone, (+)-9-deoxygoniopypyrone, (+)-goniopypyrone, and (+)-altholactone and their congeners from chiral lactonic aldehydes 27 and 36 as common intermediates are described. The key features in the syntheses are based on the in situ generation of unstable aldehydes 27 and 36 followed by their chemoselective reaction

  简捷合成（+）-goniodiol，（+）-goniotriol，（+）-8-乙酰基goniotriol，（+）-goniofufurone，（+）-9-脱氧goniopypyrone，（+）-goniopypyrone和（+）-邻甲内酯描述了它们来自手性内酯醛27和36的同类物，作为常见的中间体。合成中的关键特征是基于原位生成不稳定的醛27和36，然后它们与三异丙氧基苯基钛发生化学选择性反应，从而在C-8位提供非对映异构体28、29和37、38。检查了苯乙烯基内酯同源物对P388鼠白血病细胞的细胞毒性。
• Synthesis of (+)-goniopypyrone and (+)-goniotriol using Pd-catalyzed carbonylation
  作者：Yuki Miyazawa、Makoto Sugimoto、Ayumi Tanaka-Oda、Hidefumi Makabe

  DOI：10.1016/j.tetlet.2019.151039

  日期：2019.9

  Syntheses of (+)-goniopypyrone and (+)-goniotriol isolated from Goniothalamus giganteus were achieved. The key steps involve Pd-catalyzed carbonylation for lactone ring formation and diastereoselective reduction of ynone using the (R)-CBS catalyst and borane dimethyl sulfide complex. (C) 2019 Elsevier Ltd. All rights reserved.
• Stereoselective Syntheses of (+)-Goniotriol, (+)-8-Acetylgoniotriol, (+)-Goniodiol, (+)-9-Deoxygoniopypyrone, (+)-Altholactone, and (−)-Goniofupyrone
  作者：Chisato Mukai、Syuichi Hirai、Miyoji Hanaoka

  DOI：10.1021/jo970725u

  日期：1997.9.1

  The gamma-lactone intermediate (-)-7, derived from (+)-tricarbonyl(eta(6)-o-(trimethylsilyl)benzaldehyde)chromium (O) complex, was efficiently converted into the corresponding delta-lactone intermediate (-)-11. This second intermediate has been shown to be a versatile compound for stereoselective syntheses of natural styryllactones possessing a six-membered lactone moiety, isolated from Goniothalamus giganteus, by transforming it into (+)-goniotriol, (+)-8-acetylgoniotriol, (+)-goniodiol, (+)-9-deoxygoniopypyrone, (+)-altholactone, and (-)-goniofupyrone.