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2-iodo-3,5-dimethoxybenzyl acetate | 153786-93-7

中文名称
——
中文别名
——
英文名称
2-iodo-3,5-dimethoxybenzyl acetate
英文别名
(2-Iodo-3,5-dimethoxyphenyl)methyl acetate
2-iodo-3,5-dimethoxybenzyl acetate化学式
CAS
153786-93-7
化学式
C11H13IO4
mdl
——
分子量
336.126
InChiKey
ORWUSZDNHOIHAJ-UHFFFAOYSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

计算性质

  • 辛醇/水分配系数(LogP):
    2.2
  • 重原子数:
    16
  • 可旋转键数:
    5
  • 环数:
    1.0
  • sp3杂化的碳原子比例:
    0.36
  • 拓扑面积:
    44.8
  • 氢给体数:
    0
  • 氢受体数:
    4

上下游信息

  • 上游原料
    中文名称 英文名称 CAS号 化学式 分子量

反应信息

  • 作为反应物:
    参考文献:
    名称:
    An AC → ABC approach to taxol involving B-ring closure at C-1–C-2
    摘要:
    The treatment of keto aldehyde 13 with low-valent Ti results in a stereoselective intramolecular pinacol coupling that produces taxane synthesis intermediate 14.
    DOI:
    10.1016/s0040-4039(00)61582-4
  • 作为产物:
    描述:
    3,5-二甲氧基苄基乙酸酯双氧水溶剂黄146 作用下, 反应 6.5h, 以94%的产率得到2-iodo-3,5-dimethoxybenzyl acetate
    参考文献:
    名称:
    Taxane Synthesis through Intramolecular Pinacol Coupling at C-1−C-2. Construction and Oxidative Transformations of a C-Aromatic Taxane Diene
    摘要:
    A ten-linear-step construction of C-aromatic taxane diene 14 from ethyl isopropyl ketone, acryloyl chloride, and commercially available 8 is reported. This sequence concludes with an intramolecular pinacol coupling carried out on 13. 14 is oxidized by m-chloroperbenzoic acid and dimethyldioxirane to give 17 through intermediate epoxide 20 and by VO(acac)(2)-t-BuOOH and Mo(CO)(6)-t-BuOOH to give 13. 17 is converted efficiently into 22 upon treatment with Mo(CO)(6)-t-BuOOH, apparently through an unusual equilibration with isomeric 20, which is converted irreversibly to 22. While these oxidative transformations highlight some of the peculiar reactivity patterns characteristic of taxane-related structures, the formation of 14 through an intramolecular pinacol coupling that joins C-l and C-2 demonstrates the potential of this strategy for stereoselectively delivering advanced taxane synthesis intermediates.
    DOI:
    10.1021/jo951935e
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文献信息

  • Symmetry-based approach to oligostilbenoids: Rapid entry to viniferifuran, shoreaphenol, malibatol A, and diptoindonesin G
    作者:Youngeun Jung、Dileep Kumar Singh、Ikyon Kim
    DOI:10.3762/bjoc.12.266
    日期:——

    The recognition of the local symmetric image within benzofuran-based natural oligostilbenoids guided us to design a modular synthetic approach to these molecules by utilizing a three-step sequence consisting of Sonogashira coupling, iodocyclization, and Suzuki coupling. During our synthesis, the relative reactivities of ester, aldehyde, and alkoxy groups on the same aryl ring toward the neighboring alkyne in the iodine-mediated cyclization reactions were explored. Starting from the symmetrical 3,5-dimethoxybenzyl alcohol, this route allowed rapid access to 2,3-diarylbenzofuran, a key intermediate to several oligostilbenoid natural products, in good overall yields.

    基于苯并呋喃天然寡聚花青素中局部对称图像的识别,我们设计了一种模块化合成方法,通过使用Sonogashira偶联、环化和Suzuki偶联组成的三步序列来合成这些分子。在我们的合成过程中,探讨了在介导的环化反应中,同一芳基环上的、醛和烷基团对邻近炔烃的相对反应性。从对称的3,5-二甲氧基苄醇出发,这条路线可以快速获得2,3-二芳基苯并呋喃,这是几种寡聚花青素天然产物的关键中间体,总产率良好。
  • Reinvestigating the acyl cyclization to the precursor of diptoindonesin G
    作者:Nan-Sheng Li、Geoffrey L. Greene
    DOI:10.1016/j.tetlet.2021.152980
    日期:2021.4
    We reinvestigated the synthesis of the precursor of diptoindonesin G (2) by the intramolecular acyl cyclization of compound 1 or compound 3 in the presence of trifluoroacetic anhydride (TFAA) [1,2]. Although the reaction of 3 with TFAA generated 2 smoothly as reported, the reaction of 1 with TFAA failed to afford 2, and compound 1 was partially decomposed under the reaction conditions tested.
    我们再次研究diptoindonesin G(的前体的合成2通过化合物的分子内环化酰基)1或化合物3在三氟乙酸酐TFAA)的存在下1,2 ]。尽管如所报道的那样,3与TFAA的反应平稳地产生了2,但是1与TFAA的反应未能得到2,并且化合物1在测试的反应条件下被部分分解。
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