(E)-1,3-bis(trimethylsilyloxy)buta-1,3-diene | 61838-70-8

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (E)-1,3-bis(trimethylsilyloxy)buta-1,3-diene
• 英文别名: 1,3-BIS(TRIMETHYLSILYLOXY)-1,3-BUTADIENE；(E)-1,3-Bistrimethylsiloxy-1,3-butadiene；(E)-1,3-bis<(trimethylsilyl)oxy>buta-1,3-diene；1,3-bis (trimethylsilyloxy)butadiene；trimethyl-[(1E)-3-trimethylsilyloxybuta-1,3-dienoxy]silane
• CAS: 61838-70-8
• 化学式: C₁₀H₂₂O₂Si₂
• 分子量: 230.454
• InChiKey: XYAVQBLCFRUPDA-CMDGGOBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.72
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-1,3-bis(trimethylsilyloxy)buta-1,3-diene 在 盐酸 、 potassium dihydrogenphosphate 、 溶剂黄146 、 锌 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 24.16h， 生成 5-Amino-12-hydroxy-7-<(trimethylsilyl)oxy>-6a,7,8,9,10,10a-hexahydronaphthacene-6,9,11-trione
  参考文献：
  名称：

  Polycyclic hydroxy quinones. 28. Synthesis and Diels-Alder reactions of N,N,O-triacyl derivatives of 10-amino-9-hydroxy-1,4-anthraquinones. An efficient, regiospecific synthesis of (.+-.)-5-iminodaunomycinone, (.+-.)-4-demethoxy-5-iminodaunomycinone, and (.+-.)-daunomycinone

  摘要：

  The development of a general strategy for the construction of anthracyclinones based on a Diels-Alder reaction of substituted derivatives of 10-amino-9-hydroxy-1,4-anthraquinone is described. The key stages are (i) formation of N,O,O-triacyl derivatives of 1,4-dihydroxy-9,10-anthraquinone monoimines in a tautomer specific fashion, (ii) transacylation into N,N,O-triacyl derivatives of the corresponding 10-amino-9-hydroxy-1,4-anthraquinone, and (iii) Diels-Alder reaction with an appropriately substituted 1,3-diene regiocontrolled by steric factors. This strategy has been applied to the total synthesis of (+/-)-5-iminodaunomycinone (4) and (+/-)-4-demethoxy-5-iminodaunomycinone (3) and to a novel and short synthesis of (+/-)-daunomycinone (5).

  DOI：

  10.1021/jo00078a019
• 作为产物：
  描述：

  乙酰乙醛 、 三氟甲磺酸三甲基硅酯 在 三乙胺 作用下， 以 乙醚 为溶剂， 反应 0.17h， 以82%的产率得到(E)-1,3-bis(trimethylsilyloxy)buta-1,3-diene
  参考文献：
  名称：

  Kraegeloh, Konrad; Simchen, Gerhard, Synthesis, 1981, # 1, p. 30 - 32

  摘要：

  DOI：

文献信息

• Synthesis of Erythrina and related alkaloids. XVI Diels-Alder approach : Total synthesis of dl-erysotrine, dl-erythraline, dl-erysotramidine, dl-8-oxoerythraline and their 3-epimers.
  作者：TAKEHIRO SANO、JUN TODA、NORIAKI KASHIWABA、TAKESHI OHSHIMA、YOSHISUKE TSUDA

  DOI：10.1248/cpb.35.479

  日期：——

  Total synthesis of erythrinan alkaloids was achieved by a strategy based on the Diels-Alder reaction of activated butadienes to a dioxopyrroline. The reaction of isoquinolinopyrrolinedione (15) with 1, 3-bis-O-substituted butadienes proceeded in a regiospecific and stereoselective manner to give erythrinan derivatives (20) and (21). Lithium borohydride reduction of the adduct (20) or (21), followed by acid hydrolysis afforded the enone (33). Mesylation of 33 and subsequent demethoxycarbonylation of 42 under neutral conditions gave the dienone (43). Meerwein-Ponndorf reduction of 43 and subsequent methylation afforded erysotramidine (2a) and 8-oxoerythraline (2b). Aluminum hydride reduction of the 8-oxo derivatives (2) furnished dl-erysotrine (1a) and dl-erythraline (1b).

  基于激活的丁二烯与二氧吡咯啉进行Diels-Alder反应的策略，实现了erythrinan类生物碱的全合成。异喹啉吡咯二酮（15）与1,3-双氧取代的丁二烯反应，以区域特异性和立体选择性的方式生成erythrinan衍生物（20）和（21）。通过锂硼氢化物还原加合物（20）或（21），随后进行酸水解得到烯酮（33）。对33进行甲磺酰化，随后在中性条件下进行脱甲氧羰基化得到二烯酮（43）。对43进行Meerwein-Ponndorf还原，随后进行甲基化得到erysotramidine（2a）和8-氧代erythraline（2b）。对8-氧代衍生物（2）进行铝氢化还原得到dl-erysotrine（1a）和dl-erythraline（1b）。
• An efficient, regiospecific synthesis of (±)-Daunomycinone
  作者：T. Ross Kelly、Lakshminarayanan Ananthasubramanian、Kripinath Borah、John W. Gillard、Richard N. Goerner、Patrick F. King、Judith M. Lyding、Wen-Ghih Tsang、Jacob Vaya

  DOI：10.1016/s0040-4020(01)91516-9

  日期：1984.1

  ofregiochemistry in the Diels-Alder reactions of substituted naphthazarins is described. Application of this strategy to the synthesis of(±)-daunomycinone (2) employs two successive regiochemically controlled Diels-Alder reactions and leads to a ten-step, regiospecific synthesis of(±)-2 in 36% overall yield (Scheme 4).

  描述了控制取代萘酚的狄尔斯-阿尔德反应中区域化学的一般策略的发展。该策略在合成（±）-柔顺霉素（2）中的应用采用了两个连续的区域化学控制的Diels-Alder反应，并导致了10步的区域特异性合成（±）-2，总产率为36％（方案4） 。
• Synthesis of Erythrina and Related Alkaloids Part XLIV. Total Synthesis of Homoerythrinan Alkaloids, Schelhammericine and 3-Epischelhammericine.
  作者：Yoshisuke TSUDA、Takeshi OHSHIMA、Shinzo HOSOI、Satomi KANEUCHI、Fumiyuki KIUCHI、Jun TODA、Takehiro SANO

  DOI：10.1248/cpb.44.500

  日期：——

  Total syntheses of two homerythrinan alkaloids, schelhammericine and 3-epischelhammericine, are described. Photocycloaddition of a dioxopyrrolobenzazepine to 1-methoxy-3-trimethylsilyloxybutadiene afforded, in a regio- and stereo-specific manner, the cyclobutane derivative, which was converted to a homoerythrinan derivative by utilizing a TBAF-induced 1, 3-anionic rearrangement. The product was transformed into the title alkaloids in several steps.

  描述了两种同红藻碱（homerythrinan alkaloids），即施尔哈默碱（schelhammericine）和3-去施尔哈默碱（3-epischelhammericine）的总合成。将一个二氧基吡咯苯并氮烯（dioxopyrrolobenzazepine）与1-甲氧基-3-三甲基硅氧基丁二烯进行光环加成，得到了线性和立体特异性的环丁烷衍生物，该衍生物通过利用TBAF诱导的1,3-阴离子重排转化为同红藻衍生物。最终产物在几步反应中转化为目标碱类。
• Synthesis of Erythrina and Related Alkaloids. XXXVI. Studies toward Total Synthesis of Non-aromatic Erythrina Alkaloids. 6. Synthesis of 8-Oxo-.GAMMA.-erythroidine and 8-Oxo-cycloerythroidine, Isomers of the Natural Alkaloids.
  作者：Takehiro SANO、Jun TODA、Motoshi SHODA、Ryuzo YAMAMOTO、Hiromi ANDO、Kimiaki ISOBE、Shinzo HOSOI、Yoshisuke TSUDA

  DOI：10.1248/cpb.40.3145

  日期：——

  A study directed to the total synthesis of β-erythroidine 1, a non-aromatic Erythrina alkaloid, was conducted based on a strategy involving construction of D-furanoerythrinan via Diels-Alder reaction of furodioxopyrroline and the conversion of the resulting furan to the δ-lactone via oxidative fission of the furan ring followed by one-carbon homologation. Oxidation of the furanoerythrinan 17 with N-bromoacetamide followed by treatment with Nafion-H gave the enol γ-lactone 27. Alkaline hydrolysis of 27 followed by methylation with diazomethane gave the keto-ester 31. Alkylation of 31a with dimethylsulfoxonium methylide gave 8-oxo-γ-erythrodine (5). One-carbon homologation of 31a by Yamakawa's method using chloromethyl phenyl sulfoxide resulted in the formation of 8-ozocycloerythroidine (6). Compounds 5 and 6 are structural isomers of natural 8-oxo-β-erthroidine (2).

  一项针对非芳香性赤子豆生物碱β-赤子豆碱1的总体合成研究，基于一种策略，即通过Diels-Alder反应构建D-呋喃赤子豆烷，反应物为呋喃二氧吡咯烯，然后将生成的呋喃通过氧化开环转化为δ-内酯，随后进行一碳同系物化。用N-溴乙酰胺氧化呋喃赤子豆烷17，然后用Nafion-H处理，得到了烯醇γ-内酯27。对27进行碱性水解后，再用偶氮甲烷进行甲基化，得到酮酯31。用二甲基亚磺酰基甲烷对31a进行烷基化，得到8-氧-γ-赤子豆碱(5)。采用山川法，通过氯甲基苯基亚磺酰氧化物对31a进行一碳同系物化，形成8-氧环赤子豆碱(6)。化合物5和6是天然8-氧-β-赤子豆碱(2)的结构异构体。
• ANTHRACYCLINES. CYCLOADDITIONS OF 9-CHLORO-10-HYDROXY-1,4-ANTHRAQUINONE WITH VARIOUS BUTA-1,3-DIENES
  作者：Nand L. Agarwal、Hans W. Scheeren

  DOI：10.1246/cl.1982.1057

  日期：1982.7.5

  4-anthraquinone (10) affords an efficient, regiospecific access in two steps to tetracyclic ketones (12–14) which have been investigated as intermediates for the synthesis of anthracycline derivatives. Butadienes with a less asymmetric II-electron distribution than 9 give lower regiospecificity in cycloadditions with 10. Depending on the substituents in the used butadiene, the obtained cycloadducts are

  几种取代的丁-1,3-二烯与 9-氯-10-羟基-1,4-蒽醌 (10) 的 Diels-Alder 型环加成反应提供了一种有效的、区域特异性的分两步获得四环酮 (12-14)已被研究作为合成蒽环类衍生物的中间体。不对称 II 电子分布小于 9 的丁二烯在与 10 的环加成中具有较低的区域特异性。根据所用丁二烯中的取代基，所得环加合物在反应环境下转化为芳构化产物 (15-20)。