(S)-(E)-3-<5-Methoxy-3,4-(methylenedioxy)benzyl>-2-(3,4,5-trimethoxybenzylidene)butanolide | 146236-45-5

• 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: (S)-(E)-3-<5-Methoxy-3,4-(methylenedioxy)benzyl>-2-(3,4,5-trimethoxybenzylidene)butanolide
• 英文别名: (3E,4S)-4-[(7-methoxy-1,3-benzodioxol-5-yl)methyl]-3-[(3,4,5-trimethoxyphenyl)methylidene]oxolan-2-one
• CAS: 146236-45-5
• 化学式: C₂₃H₂₄O₈
• 分子量: 428.439
• InChiKey: SQSNXIWHBRHHDB-AHVDBNSQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 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：

  (S)-(E)-3-<5-Methoxy-3,4-(methylenedioxy)benzyl>-2-(3,4,5-trimethoxybenzylidene)butanolide 在 盐酸 、 hexaaquairon(III) perchlorate 、 三氯化硼 、 potassium carbonate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 三氟乙酸 为溶剂， 反应 12.5h， 生成 (3aS,R-Biar)-3a,4-Dihydro-8,9,10,11-tetramethoxy-6,7-(methylenedioxy)dibenzo<4,5:6,7>cycloocta<1,2-c>furan-1(3H)-one
  参考文献：
  名称：

  Total Synthesis of the Major Metabolites of Gomisin A. Synthesis of Homochiral Met A-II, Met A-III, and Met F

  摘要：

  DOI：

  10.3987/com-95-s45
• 作为产物：
  描述：

  (E)-3-methoxycarbonyl-4-<5-methoxy-3,4-(methylenedioxy)phenyl>but-3-enoic acid 在 氢氧化钾 、 sodium tetrahydroborate 、 bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate 、 氢气 、 (4R-trans)-<(2,2-dimethyl-1,3-dioxolane-4,5-diyl)bis(methylene)>bis 、 三乙胺 、 calcium chloride 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 54.0h， 生成 (S)-(E)-3-<5-Methoxy-3,4-(methylenedioxy)benzyl>-2-(3,4,5-trimethoxybenzylidene)butanolide
  参考文献：
  名称：

  五味子素代谢物的总合成

  摘要：

  实现了五味子素代谢物的总合成。通过相应的3-苄基-1-亚苄基丁内酯的氧化偶合反应，以光学纯净的形式制备了四环内酯中间体（13a-e）。Mukaiyama水合13b提供了羟基内酯（14），将其转化为SZ-M3（4）。通过连续的双键迁移到15a-e，将内酯环还原成烯丙基二醇（32a-e）和连续的双键迁移，引入了代谢物（4-11）常见的C6,7-二醇部分。乙二醇的形成。然后，甲磺酸酯33的还原完成了代谢物的合成。

  DOI：

  10.1016/0040-4020(95)00702-a

文献信息

• Polycyclic compounds, their preparation and their use as phosphodiesterases inhibitors
  申请人：TSUMURA & CO.

  公开号：EP0594890A1

  公开（公告）日：1994-05-04

  Polycyclic compounds (I) can be prepared in accordance with the following reaction formula: wherein R₁-R₈ each represents a hydrogen atom, a hydroxyl group, an alkoxyl group or a substituted or unsubstituted benzyloxy group or neighboring two groups of R₁-R₈ are coupled together to form an alkylenedioxy group; and A is an alkylene group which may be substituted by one or more alkoxycarbonyl groups, an alkenylene group which may be substituted by one or more alkoxycarbonyl groups, or a group represented by any one of the following formulas:

  多环化合物（I）可以按照以下反应式制备：其中R₁-R₈分别表示氢原子、羟基、烷氧基或取代或未取代的苄氧基，或相邻的R₁-R₈之间结合形成烷二氧基基团；A是一种烷基基团，可以被一个或多个烷氧羰基基团取代，也可以被一个或多个烷氧羰基基团取代的烯基基团，或者由以下任一公式表示的基团：
• Process for the preparation of polycyclic compounds using ferric
  申请人：Tsumura & Co.

  公开号：US05321135A1

  公开（公告）日：1994-06-14

  Polycyclic compounds (I) can be prepared in accordance with the following reaction formula: ##STR1## wherein R.sub.1 -R.sub.8 each represents a hydrogen atom, a hydroxyl group, an alkoxyl group or a substituted or unsubstituted benzyloxy group or neighboring two groups of R.sub.1 -R.sub.8 are coupled together to form an alkylenedioxy group; and A is an alkylene group which may be substituted by one or more alkoxycarbonyl groups, an alkenylene group which may be substituted by one or more alkoxycarbonyl groups, or a group represented by any one of the following formulas: ##STR2##

  (I)类多环化合物可以按照以下反应式制备：##STR1## 其中，R.sub.1-R.sub.8分别代表氢原子、羟基、烷氧基或取代或未取代苄氧基，或相邻的两个R.sub.1-R.sub.8基团耦合形成烷二氧基基团；A是一个烷基，可以被一个或多个烷氧羰基基团取代，也可以是一个烯基，可以被一个或多个烷氧羰基基团取代，或者是由下列任一公式表示的基团之一：##STR2##
• Process for the preparation of polycyclic compounds
  申请人：TSUMURA & CO.

  公开号：EP0511666A1

  公开（公告）日：1992-11-04

  Polycyclic compounds (I) can be prepared in accordance with the following reaction formula: wherein R₁-R₈ each represents a hydrogen atom, a hydroxyl group, an alkoxyl group or a substituted or unsubstituted benzyloxy group or neighboring two groups of R₁-R₈ are coupled together to form an alkylenedioxy group; and A is an alkylene group which may be substituted by one or more alkoxycarbonyl groups, an alkenylene group which may be substituted by one or more alkoxycarbonyl groups, or a group represented by any one of the following formulas:

  多环化合物 (I) 可根据以下反应式制备： 其中 R₁-R₈各自代表一个氢原子、一个羟基、一个烷氧基或一个取代或未取代的苄氧基，或 R₁-R₈ 的相邻两个基团连接在一起形成一个烷二氧基；A 是可被一个或多个烷氧羰基取代的亚烷基、可被一个或多个烷氧羰基取代的烯基、或由以下任何一个式子表示的基团：
• Synthesis of Optically Pure Gomisi Lignans: The Total Synthesis of (+)-Schizandrin, (+)-Gomisin A, and (+)-Isoschizandrin in Naturally Occurring Forms
  作者：Masahide Tanaka、Chieko Mukaiyama、Hiroshi Mitsuhashi、Masao Maruno、Takeshi Wakamatsu

  DOI：10.1021/jo00119a010

  日期：1995.7

  The total syntheses of (+)-schizandrin (1), (+)-gomisin A (2), and (+)-isoschizandrin (3) having natural configurations were accomplished. Optically pure butyrolactones ((-)-9, (-)-31) were transformed to alpha-benzylidenebutyrolactones ((+)-10, (+)-32, (+)-35). By a highly efficient iron(III) perchlorate-mediated oxidative coupling reaction of 10, 32, and 35, the key intermediates with biphenyl skeletons ((-)-11, (-)-33) were constructed with high stereoselectivity. Several methods for the stereoselective introduction of the C6-hydroxyl group were examined. For the synthesis of schizandrin and gomisin A, the Mukaiyama hydration reaction of(-)-11 and (-)-33 provided the desired products with satisfactory selectivity. For the synthesis of isoschizandrin, the stereoselective epoxidation of allylic alcohol (+)-48 was successfully utilized taking advantage of its conformational features.
• Tetrahedron Lett. 1992, 33, 4165-4168
  作者：

  DOI：——

  日期：——