threo-(-)-2,3-bis(3',4'-methylenedioxybenzyl)-1,4-butanediol diacetates | 81410-43-7

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 二苄基丁烷木脂素
• 英文名称: threo-(-)-2,3-bis(3',4'-methylenedioxybenzyl)-1,4-butanediol diacetates
• 英文别名: (R,R)-(+)-3,4-bis[3,4-(methylenedioxy)benzyl]-1,4-butanediol diacetate；ariensin；1,4-Butanediol, 2,3-bis(1,3-benzodioxol-5-ylmethyl)-, diacetate, (2R,3R)-；[(2R,3R)-3-(acetyloxymethyl)-4-(1,3-benzodioxol-5-yl)-2-(1,3-benzodioxol-5-ylmethyl)butyl] acetate
• CAS: 81410-43-7
• 化学式: C₂₄H₂₆O₈
• 分子量: 442.466
• InChiKey: GFOPJZZAXNTRGJ-PMACEKPBSA-N

物化性质

• 沸点：
  594.4±50.0 °C(Predicted)
• 密度：
  1.282±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  32
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  89.5
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  (Z)-4-(苯并[d][1,3]二氧代l-5-基)-3-(乙氧基羰基)丁3-烯酸 在 palladium dihydroxide 、 palladium on activated charcoal 氢氧化钾 、 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 Candida rugosa lipase AY 、 氢气 、 溶剂黄146 、 calcium chloride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醇 为溶剂， -30.0~20.0 ℃ 、101.33 kPa 条件下， 反应 77.5h， 生成 threo-(-)-2,3-bis(3',4'-methylenedioxybenzyl)-1,4-butanediol diacetates
  参考文献：
  名称：

  Lipase‐Catalyzed Esterification of a (±)‐2,3‐Di(Arylmethyl)‐1,4‐butanediol and Its Application to the Synthesis of (S,S)‐(+)‐Hinokinin

  摘要：

  Racemic trans-2,3-di[(3,4-methylenedioxy)benzyl]-1,4-butanediol (dihydrocubebin) 6 was enantioselectively esterified using lipases as catalysts with vinyl acetate. Optically active (SS)-1,4-butanediol 6 obtained was selectively oxygenated with a Fetizon reagent, affording (SS)-(+)-hinokinin 9 in a high yield.

  DOI：

  10.1081/scc-200051037

文献信息

• New lignans from the heartwood of cleistanthus collinus
  作者：A.S.R. Anjaneyulu、P.Atchuta Ramaiah、L.Ramachandra Row、R. Venkateswarlu、A. Pelter、R.S. Ward

  DOI：10.1016/s0040-4020(01)98893-3

  日期：1981.1

  The isolation and characterisation of five new compounds and nine known compounds from the heartwood of Cleistanthus collinus are reported. The new compounds are wodeshiol 16,3,4-dihydrotaiwanin C 20, and three new glycosides 24, 25 and 26 of diphyllin and taiwanin E The 1H and 13C NMR spectra of these compounds are also reported.

  据报道，从Cleistanthus collinus的心材中分离并鉴定了五种新化合物和九种已知化合物。这些新化合物是wodeshiol 16，3,4- dihydrotaiwaninÇ 20，和三个新的苷24，25和26山荷叶素的和taiwanin E中的1 H和13这些化合物的C NMR谱也报道。
• Synthesis, anti-virus and anti-tumour activities of dibenzylbutyrolactone lignans and their analogues
  作者：Yamu Xia、Jia You、Yuanyuan Zhang、Zhongliang Su

  DOI：10.3184/030823409x12506792542747

  日期：2009.9

  and seven analogues. Four natural lignans were prepared by this method, and five lignans were synthesised for the first time. The synthesised compounds were evaluated for anti-HIV, anti-HSV, and anti-tumour activities. Results showed that the dibenzylbutyrolactone lignans and their analogues were inactive against HIV Tat transactivation and HSV-1 in vitro, but some compounds displayed significant activity

  已开发出二苄基丁内酯木脂素及其类似物的有效合成。基于胡椒醛或藜芦醛与琥珀酸二乙酯的 Stobbe 缩合，以及与 3,4-亚甲基二氧苄基溴的烷基化反应，得到木脂素的骨架。(±)-二酸用奎宁分解并转化官能团以获得三种苄基丁内酯木脂素和七种类似物。采用该方法制备了4种天然木脂素，首次合成了5种木脂素。对合成的化合物进行了抗 HIV、抗 HSV 和抗肿瘤活性的评估。结果表明，二苄基丁内酯木脂素及其类似物在体外对 HIV Tat 反式激活和 HSV-1 无活性，但一些化合物对 MDA-MB-435 人乳腺癌细胞显示出显着的活性。
• Lignans of Piper cubeba☆
  作者：Lalit P. Badheka、Bharathi R. Prabhu、Newand B. Mulchandani

  DOI：10.1016/s0031-9422(00)81752-5

  日期：——

  Abstract Seven additional compounds have been isolated from Piper cubeba and characterized as heterotropan, magnosalin, 2,4,5-trimethoxybenzaldehyde, α- and β- O -ethyl cubebins, 5″-methoxyhinokinin and the monoacetate of dihydrocubebin. The latter four compounds are new natural products.

  摘要 从 Piper cubeba 中分离出另外七种化合物，其特征为异托品、木犀草素、2,4,5-三甲氧基苯甲醛、α-和 β-O-乙基香豆素、5″-甲氧基扁豆分裂素和二氢苦豆素的单乙酸酯。后四种化合物是新的天然产物。
• Lipase‐Catalyzed Esterification of a (±)‐2,3‐Di(Arylmethyl)‐1,4‐butanediol and Its Application to the Synthesis of (<i>S</i>,<i>S</i>)‐(+)‐Hinokinin
  作者：Toshiaki Morimoto、Hazuki Nagai、Kazuo Achiwa

  DOI：10.1081/scc-200051037

  日期：2005.3

  Racemic trans-2,3-di[(3,4-methylenedioxy)benzyl]-1,4-butanediol (dihydrocubebin) 6 was enantioselectively esterified using lipases as catalysts with vinyl acetate. Optically active (SS)-1,4-butanediol 6 obtained was selectively oxygenated with a Fetizon reagent, affording (SS)-(+)-hinokinin 9 in a high yield.