(ethoxyethyloxymethyl)tributylstannane | 66222-26-2

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机过渡后金属化合物
• 英文名称: (ethoxyethyloxymethyl)tributylstannane
• 英文别名: <(1-Ethoxyethoxy)methyl>tributylstannane；tri-n-butyl-(1-(ethoxy)ethoxy)methyltin；(Ethoxyethyloxymethyl)-tributylstannan
• CAS: 66222-26-2
• 化学式: C₁₇H₃₈O₂Sn
• 分子量: 393.198
• InChiKey: MMGGUBUDXZKNMM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.77
• 重原子数：
  20
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  (ethoxyethyloxymethyl)tributylstannane 以 四氢呋喃 为溶剂， 生成 2,6-Di-tert-butyl-4-[(1-ethoxyethoxy)methyl]-4H-thiopyran
  参考文献：
  名称：

  最简单的可分离单环噻吩。2,7-二叔丁基噻吩的合成，结构和热稳定性

  摘要：

  作为最简单的可分离单环噻吩的一个例子，由2,6-二叔丁基硫代吡啶鎓盐合成了2,7-二叔丁基噻吩（2），其热性质与X射线晶体结构一起（2）已经检查过。

  DOI：

  10.1016/s0040-4039(00)88594-9

文献信息

• Synthesis and absolute configuration of syringolide 2, an elicitor from Pseudomonas syringae pv. tomato
  作者：Shigefumi Kuwahara、Masahiko Moriguchi、Kazuhiro Miyagawa、Masako Konno、Osamu Kodama

  DOI：10.1016/0040-4039(95)00512-b

  日期：1995.5

  The enantioselective synthesis of syringolide 2, one of the two elicitors produced by Pseudomonas syringae pv. tomato, was accomplished in 11 steps from diethyl d-tartrate.

  丁香假单胞菌pv产生的两个激发子之一的丁香酚内酯2的对映体选择性合成。从酒石酸二乙酯分11步完成番茄。
• The improved convergent syntheses of arecolones and isoarecolone
  作者：John S. Ward、Leander Merritt

  DOI：10.1002/jhet.5570270636

  日期：1990.9

  Good yields of arecolone and isoarecolone were obtained by treating the N,O-dimethylamides of arecaidine and isoarecaidine, respectively, with methylmagnesium chloride. Other substituted arecolones were synthesized by this same strategy.

  通过用甲基氯化镁分别处理槟榔碱和异槟榔碱的N，O-二甲基酰胺，可以得到良好的槟榔酮和异槟榔酮的收率。通过该相同策略合成了其他取代的槟榔酮。
• Syntheses of Strychnan- and Aspidospermatan-Type Alkaloids. 10. An Enantioselective Synthesis of (−)-Strychnine through the Wieland−Gumlich Aldehyde
  作者：Martin E. Kuehne、Feng Xu

  DOI：10.1021/jo9813989

  日期：1998.12.1

  Condensations of L-tryptophan-derived 2-[(methoxycarbonyl)methyl]-3-[2(S)-(benzyloxycarbonyl)- 2-(N-b-benzylamino)ethyl]indole (6) with 4,4-dimethoxyacrolein or with 2,4-hexadienal, followed by removal of the tryptophanyl ester function, respectively gave the tetracyclic acetal (-)-methyl (2S, 3aS,5R,11bR)-3-benzyl-2,3,3a,4,5,7-hexahydro-5-(dimethoxymethyl)-1H-pyrrolo[2,3-d]carbazole-6-carboxylate (10) or the tetracyclic olefin (-)-methyl (2S,3aS,5R,11bR)-3-benzyl-2,3,3a,4,5,7-hexahydro-5-(1-propenyl)-1H-pyrrolo[2,3-d]carbazole-6-carboxylate (14). Their respective hydrolysis or oxidation provided, enantioselectively, the tetracyclic aldehyde (-)-methyl (2S,3aS,5R,11bR)3-benzyl-2,3,3a,4,5,7-hexahydro-5-formyl-1H-pyrrolo[2,3-d]carbazole-6-carboxylate (5). Its reaction with tri-n-butyl-1-(ethoxy)ethoxymethyltin and n-butyllithium, followed by oxidation of the resultant alcohol (-)-methyl (2S,3aS,5R,11bR)-3-benzyl-2,3,3a,4,5,7-hexahydro-5-(1 xi-hydroxy-2-((1-ethoxy-ethoxy))ethyl-1H-pyrrolo[2,3-d]carbazole-6-carboxylate (16) and cyclization furnished the pentacyclic ketone (-)-methyl (2S,3aS,5R,11bR)-3-benzyl-2,3,3a,4,5,7-hexahydro-3,5-ethano-12-oxo-1H-pyrrolo-2,3-d]carbazole-6-carboxylate (15). A Horner-Emmons condensation led to the unsaturated esters (-)-methyl (2S,3aS,5R,11bR)-3-benzyl-2,3,3a,4,5,7-hexahodro-3,5-ethano-12-(E and Z)-[(methoxycarbonyl)-methylene]-1H-pyrrolo[2,3-d]carbazole-6-carboxylates(19 and 20) with 17:1 E/Z selectivity. Reductions of the ester and vinylogous urethane functions in 19 led to the Wieland-Gumlich aldehyde 3 as a 6:1 anomeric hemiacetal mixture. Its condensation with malonic acid provided (-)-strychnine (1) in 5.3% overall yield and 14 steps from the tryptophan derivative 6.
• MURYOBAYASHI, TAKASHI;MIYAKE, HAJIMU;YAMATO, TAKASHI
  作者：MURYOBAYASHI, TAKASHI、MIYAKE, HAJIMU、YAMATO, TAKASHI

  DOI：——

  日期：——
• A simplest isolable monocyclic thiepin. Synthesis, structure, and thermal stability of 2,7-di-tert-butylthiepin
  作者：Kagetoshi Yamamoto、Shoko Yamazaki、Yasuji Kohashi、Ichiro Murata、Yasushi Kai、Nobuko Kanehisa、Kunio Miki、Nobutami Kasai

  DOI：10.1016/s0040-4039(00)88594-9

  日期：1982.1

  As an example of a simplest isolable monocyclic thiepin, 2,7-di-tert-butylthiepin (2) has been synthesized from 2,6-di-tert-butylthiopyrylium salt, and the thermal properties together with the X-ray crystal structure of (2) have been examined.

  作为最简单的可分离单环噻吩的一个例子，由2,6-二叔丁基硫代吡啶鎓盐合成了2,7-二叔丁基噻吩（2），其热性质与X射线晶体结构一起（2）已经检查过。