methyl 4,6-bis<<(2-methoxyethoxy)methyl>oxy>-2-iodobenzoate | 132260-56-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 4,6-bis<<(2-methoxyethoxy)methyl>oxy>-2-iodobenzoate
• 英文别名: methyl 4,6-bis[(2-methoxyethoxy)methyloxy]-2-iodobenzoate；Methyl 4,6-bis[(2-methoxyethoxy)methoxy]-2-iodobenzoate；Methyl 2-iodo-4,6-bis(2-methoxyethoxymethoxy)benzoate
• CAS: 132260-56-1
• 化学式: C₁₆H₂₃IO₈
• 分子量: 470.258
• InChiKey: CVAGTMFMRPZKTG-UHFFFAOYSA-N

物化性质

• 沸点：
  496.6±45.0 °C(Predicted)
• 密度：
  1.460±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  25
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  81.7
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl 4,6-bis<<(2-methoxyethoxy)methyl>oxy>-2-iodobenzoate 在 盐酸 、 lithium hydroxide 、 水 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 281.0h， 生成 玉米烯酮
  参考文献：
  名称：

  Synthesis of .beta.-resorcylic macrolides via organopalladium chemistry. Application to the total synthesis of (S)-zearalenone

  摘要：

  The beta-resorcylic macrolides are a class of naturally occurring 12- and 14-membered macrolides. Zearalenone (1), a 14-membered macrolide of this type, displays useful biological activity, which has led to great synthetic interest. In this paper the intramolecular coupling reaction of an organostannane with an electrophile is used to construct beta-resorcylic macrolides. The intramolecular coupling of an aryl iodide with a vinylstannane provided the highest yield of lactones. This methodology was then used to prepare (S)-zearalenone (1).

  DOI：

  10.1021/jo00008a053
• 作为产物：
  描述：

  N,N-diethyl 2,4-bis<(tert-butyldimethylsilyl)oxy>benzamide 在 叔丁基锂 、 一氯化碘 、 sodium hydride 、 sodium carbonate 作用下， 反应 46.0h， 生成 methyl 4,6-bis<<(2-methoxyethoxy)methyl>oxy>-2-iodobenzoate
  参考文献：
  名称：

  Synthesis of .beta.-resorcylic macrolides via organopalladium chemistry. Application to the total synthesis of (S)-zearalenone

  摘要：

  The beta-resorcylic macrolides are a class of naturally occurring 12- and 14-membered macrolides. Zearalenone (1), a 14-membered macrolide of this type, displays useful biological activity, which has led to great synthetic interest. In this paper the intramolecular coupling reaction of an organostannane with an electrophile is used to construct beta-resorcylic macrolides. The intramolecular coupling of an aryl iodide with a vinylstannane provided the highest yield of lactones. This methodology was then used to prepare (S)-zearalenone (1).

  DOI：

  10.1021/jo00008a053

文献信息

• The use of π-allyltricarbonyliron lactone complexes in the synthesis of the resorcylic macrolides α- and β-zearalenol
  作者：Svenja Burckhardt、Steven V. Ley

  DOI：10.1039/b201164f

  日期：2002.3.25

  A highly stereoselective synthesis of the natural products α- and β-zearalenol 1 and 2 has been achieved using π-allyltricarbonyliron lactone complexes to control the 1,5-stereochemical relationship of the oxygen functionalities found in these resorcylic macrolides.

  使用π-烯丙基三羰基铁内酯配合物控制在这些间苯二酚中发现的氧官能团的1,5-立体化学关系已实现了天然产物α-和β-玉米赤霉烯酚1和2的高度立体选择性合成大环内酯类。
• KALIVRETENOS, A.;STILLE, J. K.;HEGEDUS, L. S., J. ORG. CHEM., 56,(1991) N, C. 2883-2894
  作者：KALIVRETENOS, A.、STILLE, J. K.、HEGEDUS, L. S.

  DOI：——

  日期：——