3-methyl-5-trimethylstannanyl-furan-2-carbaldehyde | 877316-22-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-methyl-5-trimethylstannanyl-furan-2-carbaldehyde
• 英文别名: 3-methyl-5-trimethylstannylfurfural；2-Furancarboxaldehyde, 3-methyl-5-(trimethylstannyl)-；3-methyl-5-trimethylstannylfuran-2-carbaldehyde
• CAS: 877316-22-8
• 化学式: C₉H₁₄O₂Sn
• 分子量: 272.919
• InChiKey: AEHCTIVJWRXEQV-UHFFFAOYSA-N

物化性质

• 沸点：
  283.8±50.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.95
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  30.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-methyl-5-trimethylstannanyl-furan-2-carbaldehyde 在 四(三苯基膦)钯 chromium dichloride 、 N-溴代丁二酰亚胺(NBS) 、 copper(l) iodide 、 4 A molecular sieve 、 三苯基膦 、 cesium fluoride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 bipinnatin J
  参考文献：
  名称：

  A biomimetic total synthesis of (+)-intricarene

  摘要：

  An asymmetric synthesis of the furanocembrane (-)-bipinnatin J (3a) found in gorgonian corals is described. Treatment of 3a with VO(acaC)(2)-'BuOOH, followed by acetylation, gave acetoxypyranone 15. When 15 was heated in the presence of DBU, it underwent a transannular oxidopyrylium-alkene [5+2] cycloaddition producing the polycyclic diterpene (+)-intricarene 1, isolated from the coral Pseudopterogorgia kallos. The total synthesis of intricarene 1 mimics its most likely biosynthesis via oxidation of bipinnatin J (3a) in vivo. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.06.150
• 作为产物：
  描述：

  (3-甲基-2-呋喃基)甲醇 在 manganese(IV) oxide 、 正丁基锂 、 二甲羟胺盐酸盐 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 25.0h， 生成 3-methyl-5-trimethylstannanyl-furan-2-carbaldehyde
  参考文献：
  名称：

  Synthesis of a Highly Functionalized Core of Verrillin

  摘要：

  An efficient stereoselective synthesis of furanoverrillin (5), a highly functionalized core of verrillin (1), is reported. The synthetic strategy Is based on constructing bicyclic lactone 17 prior to the 10-membered ring macrocyclization. The effect of the C-4 methyl group on the furan reactivity is also discussed.

  DOI：

  10.1021/ol400872h

文献信息

• Exploring Biosynthetic Relationships among Furanocembranoids:  Synthesis of (−)-Bipinnatin J, (+)-Intricarene, (+)-Rubifolide, and (+)-Isoepilophodione B
  作者：Paul A. Roethle、Paul T. Hernandez、Dirk Trauner

  DOI：10.1021/ol062581o

  日期：2006.12.1

  The asymmetric total synthesis of (-)-bipinnatin J and its conversion into (+)-intricarene through a transannular 1,3-dipolar cycloaddition is described. In addition, the conversion of (-)-bipinnatin J into (+)-rubifolide and (+)-isoepilophodione B is reported. Biosynthetic relationships among furanocembranoids and the possible role of 1,3-dipolar cycloadditions in biosynthesis are discussed. [reaction:

  描述了（-）-联吡啶J的不对称全合成及其通过跨环1,3-偶极环加成反应转变为（+）-香烯的过程。另外，据报道，（-）-联萘醌J转化为（+）-卢比佛利特和（+）-异epilophodioneB。讨论了呋喃ce类化合物之间的生物合成关系以及1,3-偶极环加成在生物合成中的可能作用。[反应：看文字]
• Total synthesis of (+)-intricarene using a biogenetically patterned pathway from (−)-bipinnatin J, involving a novel transannular [5+2] (1,3-dipolar) cycloaddition
  作者：Bencan Tang、Christopher D. Bray、Gerald Pattenden

  DOI：10.1039/b910572g

  日期：——

  it gave (+)-intricarene 1, which is found in P. kallos, via a novel transannular [5+2] (or 1,3-dipolar) cycloaddition involving the butenolide-oxidopyrylium ion intermediate 31. We believe that this total synthesis of (+)-intricarene 1 mimics its most likely origin in nature viaoxidation of (−)-bipinnatin J (4a), presumably involving photochemically generated singlet oxygen or possibly a P450 monooxygenase

  描述了一种不对称合成的呋喃丁烯内酯基的大环二萜（-）-联吡啶类化合物J（4a），该化合物是从八方正八叶假单胞菌高联杆菌中分离出来的。合成的基础是从（+）-缩水甘油精制手性内酯取代的乙烯基碘化物26b，然后与苯乙烯基糠醛27进行分子间斯蒂勒偶联反应，生成28a，然后进行分子内Nozaki–Hiyama–Kishi烯丙基化反应，28b → 4a。VO（acac）2 – t BuO 2处理（-）-联吡啶J（4a）小时，随后互变异构hydroxypyranone产物的乙酰化7 / 8，下一个得到acetoxypyrone 30。将乙酰氧基吡喃酮30加热至乙腈在DBU存在下，得到（+）-intricarene 1，其存在于P中。kallos，通过一种新颖的跨环式[5 + 2]（或1,3-偶极）环加成反应，涉及丁烯内酯-氧化吡啶鎓离子中间体31。我们相信，（+）-tric香烯1的这种全合成模拟了其最可
• A concise total synthesis of (±)-anthecularin
  作者：Yi Li、Christopher C. Nawrat、Gerald Pattenden、Johan M. Winne

  DOI：10.1039/b819454h

  日期：——

  A total synthesis of the novel sesquiterpeneanthecularin1, isolated from Greek Anthemis auriculata, based on an intramolecular [5+2] (1,3-dipolar) cycloaddition involving the oxidopyrylium ion 12 derived from the furanmethanol 9, is described.

  描述了一种新型倍半萜an-thecularin1的全合成，该化合物从希腊的耳叶母菊（Anthemis auriculata）中分离得到，合成基于一种分子内[5+2]（1,3-偶极子）环加成反应，该反应涉及由呋喃醇9衍生的氧化吡喃离子12。
• Expedient Synthesis of (±)-Bipinnatin J
  作者：Paul A. Roethle、Dirk Trauner

  DOI：10.1021/ol052922i

  日期：2006.1.1

  A nine-step, stereoselective synthesis of bipinnatin J is described, which features a ruthenium-catalyzed Alder-ene reaction, a Stille cross coupling, and an intramolecular Nozaki-Hiyama-Kishi allylation as key steps. The biosynthetic relationship between bipinnatin J and complex polycyclic diterpenes isolated from gorgonian corals is discussed.