2-isopropoxy-5-methoxybenzaldehyde

• 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: 2-isopropoxy-5-methoxybenzaldehyde
• 英文别名: 2-Isopropoxy-5-methoxy-benzaldehyde；5-methoxy-2-propan-2-yloxybenzaldehyde
• 化学式: C₁₁H₁₄O₃
• mdl: MFCD02380380
• 分子量: 194.23
• InChiKey: RHPBEIFTLFTUQZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.363
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-isopropoxy-5-methoxybenzaldehyde 在 二异丁基氢化铝 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 lithium bromide 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 生成
  参考文献：
  名称：

  光驱动炔烃宝石加氢：Hoveyda–Grubbs 催化剂的分子内方法

  摘要：

  在 [(NHC)(η 6 -聚伞花烃)RuCl 2 ]存在下，内部炔烃的光驱动宝石氢化生成离散的钌卡宾络合物。当应用于适当设计的烯炔底物时，由此形成的反应性中间体将在复分解闭环中与束缚的烯烃结合，同时分裂出Hoveyda-Grubbs型络合物作为二级卡宾。这种用于烯烃复分解的经典催化剂的非常规方法可与现有方法相媲美，因为它安全、短、不含膦，并且使用现成的起始材料。

  DOI：

  10.1002/hlca.202200133
• 作为产物：
  描述：

  2-碘代丙烷 、 2-羟基-5-甲氧基苯甲醛 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以90%的产率得到2-isopropoxy-5-methoxybenzaldehyde
  参考文献：
  名称：

  Chiral Ru-Based Complexes for Asymmetric Olefin Metathesis:  Enhancement of Catalyst Activity through Steric and Electronic Modifications

  摘要：

  Design, synthesis, characterization, and catalytic activity of six enantiomerically pure Ru-based metathesis catalysts are disclosed (3a-3f). The new chiral catalysts were prepared through steric and electronic alterations of the parent catalyst system (3). The present studies indicate that the effect of structural modifications of chiral complex 3 does not always correspond to those of the related achiral complexes. The present findings illustrate that modified Ru complexes (3e and 3f) deliver reactivity levels that are more than 2 orders of magnitude higher than 3. Reactivity and physical data are provided that shed light on the origin of activity differences. Some members of the new generation of chiral Ru catalysts promote asymmetric ring-opening (AROM) and ring-closing (ARCM) metatheses that cannot be effected by the first generation chiral catalyst (3).

  DOI：

  10.1021/ja0302228

文献信息

• High specific activity tritium-labeled N-(2-methoxybenzyl)-2,5-dimethoxy-4-iodophenethylamine (INBMeO): A high-affinity 5-HT2A receptor-selective agonist radioligand
  作者：David E. Nichols、Stewart P. Frescas、Benjamin R. Chemel、Kenneth S. Rehder、Desong Zhong、Anita H. Lewin

  DOI：10.1016/j.bmc.2008.04.050

  日期：2008.6

  carrier added tritiated iodomethane in DMF with K(2)CO(3). Removal of the t-BOC protecting group and purification by HPLC afforded an overall yield of 43%, with a radiochemical purity of 99% and specific activity of 164Ci/mmol. The new radioligand was suitable for labeling human 5-HT(2A) receptors in two heterologous cell lines and had about 20-fold higher affinity than [(3)H]ketanserin.

  标题化合物 ([3H]INBMeO) 是通过 t-BOC 保护的二酚前体的 O,O-二甲基化反应制备的，不使用载体在 DMF 中添加氚化碘甲烷和 K(2)CO(3)。去除t-BOC保护基并通过HPLC纯化，总产率为43%，放射化学纯度为99%，比活为164Ci/mmol。新的放射性配体适用于标记两个异源细胞系中的人类 5-HT(2A) 受体，并且具有比 [(3)H] ketanserin 高约 20 倍的亲和力。
• Chiral Ru-Based Complexes for Asymmetric Olefin Metathesis:  Enhancement of Catalyst Activity through Steric and Electronic Modifications
  作者：Joshua J. Van Veldhuizen、Dennis G. Gillingham、Steven B. Garber、Osamu Kataoka、Amir H. Hoveyda

  DOI：10.1021/ja0302228

  日期：2003.10.1

  Design, synthesis, characterization, and catalytic activity of six enantiomerically pure Ru-based metathesis catalysts are disclosed (3a-3f). The new chiral catalysts were prepared through steric and electronic alterations of the parent catalyst system (3). The present studies indicate that the effect of structural modifications of chiral complex 3 does not always correspond to those of the related achiral complexes. The present findings illustrate that modified Ru complexes (3e and 3f) deliver reactivity levels that are more than 2 orders of magnitude higher than 3. Reactivity and physical data are provided that shed light on the origin of activity differences. Some members of the new generation of chiral Ru catalysts promote asymmetric ring-opening (AROM) and ring-closing (ARCM) metatheses that cannot be effected by the first generation chiral catalyst (3).
• C−H Bond Functionalization via Hydride Transfer: Synthesis of Dihydrobenzopyrans from <i>ortho</i>-Vinylaryl Akyl Ethers
  作者：Kevin M. McQuaid、Jonathan Z. Long、Dalibor Sames

  DOI：10.1021/ol900915p

  日期：2009.7.16

  The hydride transfer initiated cyclization ("HT-cyclization") of aryl alkyl ethers, which leads to direct coupling of sp(3) C-H bonds and activated alkenes, is reported. Readily available salicylaldehyde derived ethers are converted in one step to dihydrobenzopyrans, an important class of heteroarenes frequently found in biologically active compounds. This process has not been previously reported, in contrast to known HT-cyclizations of the corresponding tert-amines ("tert-amino effect" reactions).
• Light‐Driven Alkyne <i>gem</i> ‐Hydrogenation: An Intramolecular Approach to <i>Hoveyda–Grubbs</i> Catalysts
  作者：Tomas J. Saiegh、Tobias Biberger、Raphael J. Zachmann、Alois Fürstner

  DOI：10.1002/hlca.202200133

  日期：2022.12

  internal alkynes in the presence of [(NHC)(η6-cymene)RuCl2] generates discrete ruthenium carbene complexes. When applied to appropriately designed enyne substrates, the reactive intermediates thus formed will engage the tethered olefin in metathetic ring closure while splitting off a Hoveyda–Grubbs-type complex as secondary carbene. This unconventional approach to these classical catalysts for olefin

  在 [(NHC)(η 6 -聚伞花烃)RuCl 2 ]存在下，内部炔烃的光驱动宝石氢化生成离散的钌卡宾络合物。当应用于适当设计的烯炔底物时，由此形成的反应性中间体将在复分解闭环中与束缚的烯烃结合，同时分裂出Hoveyda-Grubbs型络合物作为二级卡宾。这种用于烯烃复分解的经典催化剂的非常规方法可与现有方法相媲美，因为它安全、短、不含膦，并且使用现成的起始材料。