(Z)-<2-methyl-3-(2-tetrahydropyranyloxy)-1-propenyl>trimethylstannane | 139896-11-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: (Z)-<2-methyl-3-(2-tetrahydropyranyloxy)-1-propenyl>trimethylstannane
• 英文别名: 3-(2-tetrahydropyranyl)oxy-2-methyl-1(Z)-propenyltrimethylstannane；trimethyl-[2-methyl-3-(oxan-2-yloxy)prop-1-enyl]stannane
• CAS: 139896-11-0；126822-64-8
• 化学式: C₁₂H₂₄O₂Sn
• 分子量: 319.031
• InChiKey: NLNWXNSCAGVHRS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.35
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 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：

  (Z)-<2-methyl-3-(2-tetrahydropyranyloxy)-1-propenyl>trimethylstannane 在 tris(dibenzylideneacetone)dipalladium (0) 、 三苯胂 、 4-甲基苯磺酸吡啶 、 乙硫醇钠 作用下， 以 乙二醇二甲醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 19.5h， 生成 2-[3-methoxy-2-[(Z)-3-methyl-4-(oxan-2-yloxy)but-2-enyl]-5-(2-phenylethyl)phenoxy]oxane
  参考文献：
  名称：

  A new preparation of 2,5-dihydro-1-benzoxepins using Mitsunobu cyclization, and the synthesis of natural radulanins

  摘要：

  Mitsunobu cyclization of o-[4-hydroxy-3-methyl-2(Z)-butenyl]pheno 2a effected selective seven-membered cyclization to give 3-methyl-2,5-dihydro-1-benoxepin la. Using this procedure, natural radulanin A and radulanin A methyl ether were synthesized effectively. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00676-6

文献信息

• Synthesis of Two Naturally Occurring 3-Methyl-2,5-dihydro-1-benzoxepin Carboxylic Acids
  作者：Seiji Yamaguchi、Nao Tsuchida、Masahiro Miyazawa、Yoshiro Hirai

  DOI：10.1021/jo050550l

  日期：2005.9.1

  Two naturally occurring 3-methyl-2,5-dihydro-1-benzoxepin carboxylic acids, 6-hydroxy-3-methyl-8-(phenylethyl)-2,5-dihydro-1-benzoxepin-9-carboxylic acid (radulanin E) (1) and 9-hydroxy-3-methyl-2,5-dihydro-1-benzoxepin-7-carboxylic acid (2), were synthesized using Stille coupling followed by Mitsunobu cyclization.

  两种天然存在的3-甲基-2,5-二氢-1-苯并二甲苯甲酸，6-羟基-3-甲基-8-（苯乙基）-2,5-二氢-1-苯并二甲苯胺-9-羧酸（鲁丹宁E ）（1）和9-羟基-3-甲基-2,5-二氢-1-苯并二甲基-7-羧酸（2）的合成方法是使用Stille偶联，然后进行Mitsunobu环化。
• Total synthesis of furanocembranolides. 2. Macrocyclization studies culminating in the synthesis of a dihydropseudopterolide and gorgiacerone. Related furanocembranolide interconversions.
  作者：Christopher M. Rayner、Peter C. Astles、Leo A. Paquette

  DOI：10.1021/ja00036a046

  日期：1992.5

  The acetaldehydes 7, 14, 22, and 29 were screened for their ability to undergo macrocyclization. These substrates were made available as a consequence of the generality of Pd(0)-catalyzed vinylstannane couplings to bromides 12. Although molecular mechanics calculations indicated there to be no conformational deterrent to ring closure, 7 failed to undergo intramolecular Prins reaction and 14 did not

  对乙醛 7、14、22 和 29 进行大环化的能力进行了筛选。由于 Pd(0) 催化的乙烯基锡烷与溴化物 12 偶联的普遍性，这些底物可用。尽管分子力学计算表明对闭环没有构象威慑，但 7 未能进行分子内 Prins 反应，14 没有进入烯丙基硅烷-甲醛缩合反应
• Paquette, Leo A.; Rayner, Christopher M.; Doherty, Annette M., Journal of the American Chemical Society, 1990, vol. 112, # 10, p. 4078 - 4079
  作者：Paquette, Leo A.、Rayner, Christopher M.、Doherty, Annette M.

  DOI：——

  日期：——
• PAQUETTE, LEO A.;RAYNER, CHRISTOPHER M.;DOHERTY, ANNETTE M., J. AMER. CHEM. SOC., 112,(1990) N0, C. 4078-4079
  作者：PAQUETTE, LEO A.、RAYNER, CHRISTOPHER M.、DOHERTY, ANNETTE M.

  DOI：——

  日期：——
• Total synthesis of furanocembranolides. 3. A concise convergent route to acerosolide
  作者：Leo A. Paquette、Peter C. Astles

  DOI：10.1021/jo00053a031

  日期：1993.1

  The first synthesis of a 14-membered furanocembranolide has been achieved. The target molecule, acerosolide, contains two stereogenic cetners whose relative and absolute configuration have not previously been assigned. MM2 calculations performed during the course of the present work suggest their configuration to be 1(S*),10(R*). The synthesis began by SnCl2-promoted condensation of allylstannane 6 to aldehyde 7 so as to achieve regioreversed condensation and formation of the extended allylic alcohol 9. Acid-catalyzed lactonization and 2-fold oxidation via the bis-selenide gave butenolide 11 and subsequently the derived bromide 12b. Palladium(0)-catalyzed condensation of 12b with vinylstannane 13 provided seco-cembrane 14. Following the elaboration of 14 into bromo aldehyde 16, macrocyclization was effected with chromous chloride. The single homoallylic alcohol produced by this means underwent oxidation to give acerosolide, as deduced by proper spectral comparison with the natural product.