[(2R,4aR,6S,7R,9aS)-6-[(Z)-2-bromoethenyl]-7-methyl-2-phenyl-4,4a,6,9a-tetrahydro-[1,3]dioxino[5,4-b]oxepin-7-yl]oxy-tert-butyl-dimethylsilane | 213815-43-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二恶烷
• 英文名称: [(2R,4aR,6S,7R,9aS)-6-[(Z)-2-bromoethenyl]-7-methyl-2-phenyl-4,4a,6,9a-tetrahydro-[1,3]dioxino[5,4-b]oxepin-7-yl]oxy-tert-butyl-dimethylsilane
• CAS: 213815-43-1
• 化学式: C₂₃H₃₃BrO₄Si
• 分子量: 481.502
• InChiKey: XRZAUGABJVMMEU-XZXXOFADSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.11
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [(2R,4aR,6S,7R,9aS)-6-[(Z)-2-bromoethenyl]-7-methyl-2-phenyl-4,4a,6,9a-tetrahydro-[1,3]dioxino[5,4-b]oxepin-7-yl]oxy-tert-butyl-dimethylsilane 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 copper(l) iodide 、 P(furyl)3 、 四丁基氟化铵 作用下， 以 二甲基亚砜 为溶剂， 生成 (2R,4aR,6S,7R,9aS)-6-((1Z,3Z)-Hepta-1,3,6-trienyl)-7-methyl-2-phenyl-4a,6,7,9a-tetrahydro-4H-1,3,5-trioxa-benzocyclohepten-7-ol
  参考文献：
  名称：

  Synthesis of the H ring of gambierol

  摘要：

  Stereoselective synthesis of the H ring of gambierol was achieved from 2-deoxy-D-ribose by using the intramolecular reaction of allylstannane with aldehyde as a key step. Mollified Stille coupling was successfully applied for the construction of the triene side chain. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01312-4
• 作为产物：
  描述：

  tert-Butyl-[(2R,4aR,6S,7R,9aS)-6-(2,2-dibromo-vinyl)-7-methyl-2-phenyl-4a,6,7,9a-tetrahydro-4H-1,3,5-trioxa-benzocyclohepten-7-yloxy]-dimethyl-silane 在 四(三苯基膦)钯 、 三正丁基氢锡 作用下， 以 苯 为溶剂， 以82%的产率得到[(2R,4aR,6S,7R,9aS)-6-[(Z)-2-bromoethenyl]-7-methyl-2-phenyl-4,4a,6,9a-tetrahydro-[1,3]dioxino[5,4-b]oxepin-7-yl]oxy-tert-butyl-dimethylsilane
  参考文献：
  名称：

  Synthesis of the H ring of gambierol

  摘要：

  Stereoselective synthesis of the H ring of gambierol was achieved from 2-deoxy-D-ribose by using the intramolecular reaction of allylstannane with aldehyde as a key step. Mollified Stille coupling was successfully applied for the construction of the triene side chain. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01312-4

文献信息

• A simple and practical method for the stereoselective synthesis of (Z)-1-iodo-1-alkenes from 1,1-diiodo-1-alkenes
  作者：Isao Kadota、Hirokazu Ueno、Akio Ohno、Yoshinori Yamamoto

  DOI：10.1016/j.tetlet.2003.09.166

  日期：2003.11

  Treatment of the 1,1-diiodo-1-alkenes 8, prepared from the corresponding aldehydes with CI4/PPh3, with ZnCu/AcOH in THF–MeOH gave the (Z)-1-iodo-1-alkenes 9, selectively, in good yields.

  用Cl 4 / PPh 3由相应的醛制备的1,1-二碘-1-烯烃8用THF / MeOH中的ZnCu/ AcOH处理，得到（Z）-1-碘-1-烯烃9，选择性高产。
• Synthesis of the H ring of gambierol
  作者：Isao Kadota、Akio Ohno、Yasuhisa Matsukawa、Yoshinori Yamamoto

  DOI：10.1016/s0040-4039(98)01312-4

  日期：1998.8

  Stereoselective synthesis of the H ring of gambierol was achieved from 2-deoxy-D-ribose by using the intramolecular reaction of allylstannane with aldehyde as a key step. Mollified Stille coupling was successfully applied for the construction of the triene side chain. (C) 1998 Elsevier Science Ltd. All rights reserved.