4,6-bis<<(2-methoxyethoxy)methyl>oxy>-2-iodobenzoic acid | 132260-57-2

• 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: 4,6-bis<<(2-methoxyethoxy)methyl>oxy>-2-iodobenzoic acid
• 英文别名: 2-Iodo-4,6-bis(2-methoxyethoxymethoxy)benzoic acid
• CAS: 132260-57-2
• 化学式: C₁₅H₂₁IO₈
• 分子量: 456.231
• InChiKey: MJURTOAWJZFMBR-UHFFFAOYSA-N

物化性质

• 沸点：
  531.9±50.0 °C(Predicted)
• 密度：
  1.538±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  24
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  92.7
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  4,6-bis<<(2-methoxyethoxy)methyl>oxy>-2-iodobenzoic acid 在 盐酸 作用下， 以 四氢呋喃 为溶剂， 反应 216.0h， 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：

  methyl 4,6-bis<<(2-methoxyethoxy)methyl>oxy>-2-iodobenzoate 在 lithium hydroxide 、 水 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 65.0h， 以86%的产率得到4,6-bis<<(2-methoxyethoxy)methyl>oxy>-2-iodobenzoic acid
  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

• Solid-Phase Synthesis of Macrocyclic Systems by a Cyclorelease Strategy: Application of the Stille Coupling to a Synthesis of (S)-Zearalenone
  作者：K. C. Nicolaou、Nicolas Winssinger、Joaquin Pastor、Fiona Murphy

  DOI：10.1002/(sici)1521-3773(19981002)37:18<2534::aid-anie2534>3.0.co;2-f

  日期：1998.10.2

  No heteroatom required! In many solid-phase syntheses, after the release from the polymer support a heteroatom (e.g. O, S, N) remains in the substrate as a residue of a linking protecting group. With polymer-bound tin reagents cleavage and cyclization of the substrate with C-C bond formation (see picture) can now be achieved by intramolecular Stille coupling. S=substrate.

  无需杂原子！在许多固相合成中，从聚合物载体上释放后，杂原子（例如O，S，N）作为连接保护基团的残基保留在底物中。现在，通过与聚合物结合的锡试剂，可以通过分子内Stille偶联实现具有CC键形成的底物的裂解和环化（参见图片）。S ＝底物。
• 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：——