1-Methoxy-3-(tributylstannyl)propene | 139427-04-6

• 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: 1-Methoxy-3-(tributylstannyl)propene
• 英文别名: 3-(tributylstannyl)-1-methoxypropene；γ-methoxyallylstannane
• CAS: 139427-04-6
• 化学式: C₁₆H₃₄OSn
• 分子量: 361.155
• InChiKey: OQKMZJIJCPFOMV-UHFFFAOYSA-N

物化性质

• 沸点：
  352.1±52.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.0
• 重原子数：
  18
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-Methoxy-3-(tributylstannyl)propene 在 camphor-10-sulfonic acid 、 二异丁基氢化铝 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 0.5h， 生成
  参考文献：
  名称：

  雪茄毒素CTX3C EFGH环系统的收敛合成

  摘要：

  通过使用α-氯乙酰氧基醚和/或O，S-乙缩醛的分子内烯丙基化以及随后的闭环易位，研究了瓜瓜毒素CTX3C EFGH环段的收敛合成。还描述了一种制备γ-烷氧基烯丙基锡烷的新方法。

  DOI：

  10.1016/j.tet.2015.04.106

文献信息

• Total synthesis of brevenal
  作者：Hiroyoshi Takamura、Yuji Yamagami、Takayuki Kishi、Shigetoshi Kikuchi、Yuichi Nakamura、Isao Kadota、Yoshinori Yamamoto

  DOI：10.1016/j.tet.2010.05.069

  日期：2010.7

  The convergent total synthesis of brevenal, a non-toxic brevetoxin antagonist, has been achieved. The ABC ring segment and the E ring precursor were connected by the intramolecular allylation followed by ring-closing metathesis to furnish the pentacyclic ether compound. An alternative route to the key synthetic intermediate, a pentacyclic ether core, was also examined. The right- and left-hand side

  已经实现了无毒性的brevetoxin拮抗剂brevenal的聚合全合成。ABC环段和E环前体通过分子内烯丙基化然后闭环易位连接以提供五环醚化合物。还研究了通往关键合成中间体五环醚核的另一种途径。Wittig和Horner–Wadsworth–Emmons反应分别引入了右侧链和左侧链，以提供brevenal（1）。
• Improved Synthesis of the A–E Ring Segment of Ciguatoxin CTX3C by Using Intramolecular Allylations
  作者：Tokihiro Tanaka、Hiroki Asakura、Rie Fujiwara、Kentaro Kumamoto、Hiroaki Izuka、Kengo Shiroma、Hiroyoshi Takamura、Isao Kadota

  DOI：10.1246/bcsj.20170390

  日期：2018.4.15

  An improved synthesis of the A–E ring segment of ciguatoxin CTX3C is described. The E ring segment was synthesized by the intramolecular reaction of allylic stannane and aldehyde with high stereoselectivity. Construction of the A–E ring framework was performed by using the intramolecular allylation of α-acetoxy ether followed by ring-closing metathesis.

  描述了雪卡毒素 CTX3C 的 A-E 环段的改进合成。E环段由烯丙基锡烷和醛的分子内反应合成，具有高立体选择性。A-E环骨架的构建是通过使用α-乙酰氧基醚的分子内烯丙基化然后闭环复分解来进行的。
• Total Synthesis of (−)-Brevisin: A Concise Synthesis of a New Marine Polycyclic Ether
  作者：Takefumi Kuranaga、Naohito Ohtani、Ryosuke Tsutsumi、Daniel G. Baden、Jeffrey L. C. Wright、Masayuki Satake、Kazuo Tachibana

  DOI：10.1021/ol102925d

  日期：2011.2.18

  The first and highly efficient total synthesis of (−)-brevisin has been achieved. The title compound was synthesized in only 29 steps (longest linear sequence) from commercially available starting materials. The synthesis provided over 70 mg of a marine polycyclic ether compound.

  已经实现了 (-)-brevisin 的第一个高效全合成。标题化合物仅通过 29 个步骤（最长的线性序列）从市售原料合成。该合成提供了超过 70 毫克的海洋多环醚化合物。
• Convergent synthesis of the A–E ring segment of ciguatoxin CTX3C
  作者：Isao Kadota、Takashi Abe、Miyuki Uni、Hiroyoshi Takamura、Yoshinori Yamamoto

  DOI：10.1016/j.tet.2009.07.037

  日期：2009.9

  A convergent synthesis of the A–E ring segment of ciguatoxin CTX3C was achieved via the intramolecular allylation of an α-chloroacetoxy ether and subsequent ring-closing metathesis.

  通过α-氯乙酰氧基醚的分子内烯丙基化和随后的闭环易位，实现了瓜瓜毒素CTX3C A–E环段的融合合成。
• Total synthesis of (+)-calyculin A
  作者：David A. Evans、James R. Gage、James L. Leighton

  DOI：10.1021/ja00050a024

  日期：1992.11

  A convergent asymmetric synthesis of the marine natural product calyculin A has been accomplished through the union of the two subunits comprising the C1-C25 and C26-C37 portions of the molecule. These fragments were constructed utilizing auxiliary-based asymmetric aldol, alkylation, hydroxylation, and Michael reactions to establish 10 of the 15 stereogenic centers, The remaining chirality was incorporated through internal asymmetric induction. Stereoselective Wittig coupling of the two fragments and subsequent deprotection provided synthetic calyculin A. The spectral properties of the synthetic material were in complete agreement with those of the natural material except for the optical rotation which was equal and opposite in sign to that of the natural material. The absolute configuration of (-)-calyculin A has thus been shown to be opposite to that illustrated in structure 1.