Methyl 3-(bromomethyl)-4-iodobenzoate | 1187237-61-1

• 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 3-(bromomethyl)-4-iodobenzoate
• CAS: 1187237-61-1
• 化学式: C₉H₈BrIO₂
• 分子量: 354.97
• InChiKey: AKTNVDXJZMKQNS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Methyl 3-(bromomethyl)-4-iodobenzoate 在 sodium tetrahydroborate 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 8.0h， 生成 methyl 3-(3-hydroxy-2-(hydroxymethyl)propyl)-4-iodobenzoate
  参考文献：
  名称：

  Pd-Catalyzed Desymmetric Intramolecular O-Arylation Reaction: Enantioselective Synthesis of (3,4-Dihydro-2H-chromen-3-yl)methanols

  摘要：

  An enantioselective intramolecular O-arylation was achieved through desymmetrization with Pd-catalyzed coupling reactions. The intramolecular asymmetric aryl C-O coupling reactions of 2-(2-haloaryl)propane-1,3-diols led to the enantioselective formation of chiral (3,4-dihydro-2H-chromen-3-yl)methanols in good yields and high enantiomeric selectivity.

  DOI：

  10.1021/ol402911y
• 作为产物：
  描述：

  4-碘-3-甲基苯甲酸甲酯 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 四氯化碳 为溶剂， 生成 Methyl 3-(bromomethyl)-4-iodobenzoate
  参考文献：
  名称：

  Design, synthesis and identification of novel colchicine-derived immunosuppressant

  摘要：

  Synthesis and biological evaluation of various colchicine analogues through the mixed-lymphocyte reaction (MLR), lymphoproliferation, and inhibitory effects on the inflammatory genes are described. In addition, a new series of immunosuppressive agents developed on the structural basis of colchicine, as well as their structure-activity relationships is reported. The most potent analogue 20a exhibited an excellent immunosuppressive activity on in vivo skin-allograft model, which is comparable to that of cyclosporin A. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.05.054

文献信息

• Hydroxylamines As Bifunctional Single-Nitrogen Sources for the Rapid Assembly of Diverse Tricyclic Indole Scaffolds
  作者：Liangxin Fan、Jiamao Hao、Jingxun Yu、Xiaojun Ma、Jingjing Liu、Xinjun Luan

  DOI：10.1021/jacs.0c00403

  日期：2020.4.8

  for the construction of n-membered (n>3) N-heterocycles, rely upon two chemical operations by involving sequential nucleophilic and electrophilic C-N bond formations. Here, we report a highly efficient cascade of alkyne insertion/C-H activation/amination for the rapid preparation of a myriad of tricyclic indoles, in a single-step transformation, by using bifunctional secondary hydroxylamines. Noteworthy

  使用羟胺衍生物作为单一氮源构建 n 元 (n>3) N-杂环的常规方法依赖于两个化学操作，涉及顺序亲核和亲电 CN 键的形成。在这里，我们报告了一种高效的炔插入/CH 活化/胺化级联，通过使用双功能仲羟胺，在一步转化中快速制备无数的三环吲哚。值得注意的是，明智地选择适用的氨基试剂，使芳基碘化物能够预先氧化加成到初始 Pd(0) 物种并随后形成两个 CN 键，是该反应成功的关键。对照实验表明，五元钯环中间体在促进最终胺化环闭合方面起着至关重要的作用。