(3R*,4R*)-3-(3,4,5-trimethoxybenzyl)-4-(3,4,5-trimethoxybenzyl)-4,5-dihydro-2(3H)-furanone | 93395-16-5

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 呋喃类木脂素
• 英文名称: (3R*,4R*)-3-(3,4,5-trimethoxybenzyl)-4-(3,4,5-trimethoxybenzyl)-4,5-dihydro-2(3H)-furanone
• 英文别名: (3S,4S)-3,4-bis[(3,4,5-trimethoxyphenyl)methyl]oxolan-2-one
• CAS: 93395-16-5；110454-78-9；115587-59-2；115587-60-5；117407-00-8；135272-24-1；147783-14-0
• 化学式: C₂₄H₃₀O₈
• 分子量: 446.497
• InChiKey: VUNCHONBJWJYID-SJORKVTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  32
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  81.7
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (3R*,4R*)-3-(3,4,5-trimethoxybenzyl)-4-(3,4,5-trimethoxybenzyl)-4,5-dihydro-2(3H)-furanone 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以58%的产率得到(2R*,3R*)-2,3-dihydroxymethyl-1,4-bis-(3,4,5-trimethoxyphenyl)butane
  参考文献：
  名称：

  Indonesian Medicinal Plants. IV. On the Constituents of the Bark of Fagara rhetza (Rutaceae). (2). Lignan Glycosides and Two Apioglucosides.

  摘要：

  从印度尼西亚弗洛雷斯岛产药用植物飞龙掌血（芸香科）树皮中分离得到2个新的木脂素苷，命名为hazaleanin A（1）和hazaleanin B（2）；2个新的芹糖葡萄糖苷，命名为异丙基芹糖葡萄糖苷（3）和4-羟基愈创木酚芹糖葡萄糖苷（4）。根据化学和物理化学证据，包括1型的苷元衍生物的不对称合成，阐述了1、2、3、4的化学结构。

  DOI：

  10.1248/cpb.40.2639
• 作为产物：
  描述：

  (+/-)-4-(3,4,5-trimethoxyphenyl)-3-methoxycarbonylbutanoic acid 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 potassium tert-butylate 、 sodium hydride 、 三乙胺 、 calcium chloride 、 nickel dichloride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 37.33h， 生成 (3R*,4R*)-3-(3,4,5-trimethoxybenzyl)-4-(3,4,5-trimethoxybenzyl)-4,5-dihydro-2(3H)-furanone
  参考文献：
  名称：

  使用 NaBH4–NiCl2 通过非对映选择性还原 α-亚苄基-β-苄基-γ-丁内酯简单合成反式-α,β-二苄基-γ-丁内酯木脂素

  摘要：

  反式-α,β-二苄基-γ-丁内酯木脂素是通过使用NaBH4-NiCl2立体选择性还原α-苄叉-β-苄基-γ-丁内酯合成的。发现还原是通过氢化物与 α-亚苄基-β-苄基-γ-丁内酯的共轭加成和所得金属烯醇化物的立体选择性质子化来进行的。立体选择性是由 1,3-烯丙基应变诱导的 α-苄基的苯基部分的构象刚性带来的。

  DOI：

  10.1246/bcsj.69.2281

文献信息

• Indonesian Medicinal Plants. IV. On the Constituents of the Bark of Fagara rhetza (Rutaceae). (2). Lignan Glycosides and Two Apioglucosides.
  作者：Hirotaka SHIBUYA、Yasuyuki TAKEDA、Ru-song ZHANG、Akihiko TANITAME、Yen-Li TSAI、Isao KITAGAWA

  DOI：10.1248/cpb.40.2639

  日期：——

  Two new lignan glycosides, named hazaleanin A (1) and hazaleanin B (2), and two new apioglucosides, named isopropyl apioglucoside (3) and 4-hydroxyguaiacol apioglucoside (4), were isolated from the bark of Fagara rhetza (Rutaceae), an Indonesian medicinal plant from Flores Island, Indonesia. The chemical structures of 1, 2, 3, and 4 have been elucidated on the basis of chemical and physicochemical evidence, including a chiral synthesis of an aglycone derivative of 1.

  从印度尼西亚弗洛雷斯岛产药用植物飞龙掌血（芸香科）树皮中分离得到2个新的木脂素苷，命名为hazaleanin A（1）和hazaleanin B（2）；2个新的芹糖葡萄糖苷，命名为异丙基芹糖葡萄糖苷（3）和4-羟基愈创木酚芹糖葡萄糖苷（4）。根据化学和物理化学证据，包括1型的苷元衍生物的不对称合成，阐述了1、2、3、4的化学结构。
• Ruthenium dioxide in fluoro acid medium: I. A new agent in the biaryl oxidative coupling. Application to the synthesis of non phenolic bisbenzocyclooctadiene lignan lactones.
  作者：Y Landais、J.-P Robin、A Lebrun

  DOI：10.1016/s0040-4020(01)80904-2

  日期：——

  very efficient agent for the oxidative coupling of non phenolic lignans and their derivatives, and this method was applied to the total synthesis of (+/-)-neoisostegane 2a and (+/-)-steganolide A 2b. This procedure was also used to obtain the first stereospecific synthesis of a cis-bisbenzocyclooctadiene lactone, the (+/-)-deoxyschizandrin 17, of which, was afforded by a short reduction sequence.

  氟酸介质中的二水合钌（IV）被发现是非酚类木脂素及其衍生物氧化偶联的非常有效的试剂，该方法被用于（+/-）-neosoostegane 2a和（ +/-）-硬脂酸内酯A 2b。该方法还用于获得顺式-双苯并环辛二烯内酯的第一个立体有择合成，其（+/-）-脱氧五味子甲酸酯17是通过短还原序列提供的。
• Synthesis of diarylbutanes from cordigerines and reinvestigation of their oxidative couplings in deoxyschizandrins. - An unusual formation of phenyltetralin lignans -
  作者：Y. Landais、A. Lebrun、V. Lenain、J.-P. Robin

  DOI：10.1016/s0040-4039(00)95617-x

  日期：——

  Dibenzylbutanolide lignans including cordigerines were synthetized and transformed in the corresponding diarylbutane lignans which were submitted to non-phenolic oxidative coupling conditions by using RuO2 or Tl2O3 in trifluoroacetic medium to give deoxyschizandrins. A concurrently aryl-benzyl coupling leads to the formation of the corresponding phenyltetralin of which the structure was confirmed by

  通过在三氟乙酸介质中使用RuO 2或Tl 2 O 3合成包括相应的二芳基丁烷木脂素在内的二苄基丁醇木脂素并在相应的二芳基丁烷木脂素中转化，将其转化为非酚类氧化偶联条件。同时发生的芳基-苄基偶联导致形成相应的苯基四氢萘，其结构已通过全合成得到证实。
• Synthetic butanolide and tetrahydrofuran lignans with platelet activating factor antagonist activity
  作者：SA Coran、M Bambagiotti-Alberti、F Melani、V Giannellini、FF Vincieri、N Mulinacci、R Sala、E Moriggi

  DOI：10.1016/0223-5234(91)90200-7

  日期：1991.9

  Several butanolide and tetrahydrofuran lignans were synthesized to be comparatively tested as platelet activating factor (PAF) antagonists. In particular, the influence of the tetrahydrofurans ether oxygen as compared with the gamma-lactone system of butanolides was evaluated, showing that the two classes of compounds were practically bioisosters. Molecular modelling and semi-empirical calculation were used to rationalize the collected data.
• Simple Synthesis of<i>trans</i>-<i>α</i>,<i>β</i>-Dibenzyl-<i>γ</i>-butyrolactone Lignans by Diastereoselective Reduction of<i>α</i>-Benzylidene-<i>β</i>-benzyl-<i>γ</i>-butyrolactones Using NaBH₄–NiCl₂
  作者：Yasunori Moritani、Chiaki Fukushima、Toshikazu Miyagishima、Hiroshi Ohmizu、Tameo Iwasaki

  DOI：10.1246/bcsj.69.2281

  日期：1996.8

  ne lignans were synthesized by stereoselective reduction of α-benzylidene-β-benzyl-γ-butyrolactones using NaBH4–NiCl2. The reduction is found to proceed via conjugate addition of a hydride to an α-benzylidene-β-benzyl-γ-butyrolactone and the stereoselective protonation of the resulting metal enolate. The stereoselectivity would be brought about by the conformational rigidity of the phenyl moiety of

  反式-α,β-二苄基-γ-丁内酯木脂素是通过使用NaBH4-NiCl2立体选择性还原α-苄叉-β-苄基-γ-丁内酯合成的。发现还原是通过氢化物与 α-亚苄基-β-苄基-γ-丁内酯的共轭加成和所得金属烯醇化物的立体选择性质子化来进行的。立体选择性是由 1,3-烯丙基应变诱导的 α-苄基的苯基部分的构象刚性带来的。