1-cyclopropyl-2,4-dimethoxybenzene | 1158985-15-9

• 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: 1-cyclopropyl-2,4-dimethoxybenzene
• 英文别名: 2,4-dimethoxycyclopropylbenzene；2,4-dimethoxy-1-cyclopropylbenzene
• CAS: 1158985-15-9
• 化学式: C₁₁H₁₄O₂
• 分子量: 178.231
• InChiKey: UQZXNUWCWFXFPT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  cyclopropylboronic acid MIDA ester 、 1-氯-2,4-二甲氧基苯 在 2-双环己基膦-2',6'-二甲氧基联苯 、 palladium diacetate 、 potassium phosphate 、 水 作用下， 以 1,4-二氧六环 为溶剂， 反应 6.67h， 以97%的产率得到1-cyclopropyl-2,4-dimethoxybenzene
  参考文献：
  名称：

  Knapp, David M.; Gillis, Eric P.; Burke, Martin D., Journal of the American Chemical Society, 2009, vol. 131, p. 6961 - 6963

  摘要：

  DOI：

文献信息

• Tri(1-adamantyl)phosphine: Expanding the Boundary of Electron-Releasing Character Available to Organophosphorus Compounds
  作者：Liye Chen、Peng Ren、Brad P. Carrow

  DOI：10.1021/jacs.6b03215

  日期：2016.5.25

  We report here the remarkable properties of PAd3, a crystalline air-stable solid accessible through a scalable SN1 reaction. Spectroscopic data reveal that PAd3, benefiting from the polarizability inherent to large hydrocarbyl groups, exhibits unexpected electron releasing character that exceeds other alkylphosphines and falls within a range dominated by N-heterocyclic carbenes. Dramatic effects in

  我们在这里报告了 PAd3 的显着特性，PAd3 是一种结晶的空气稳定固体，可通过可扩展的 SN1 反应获得。光谱数据显示，PAd3 受益于大烃基固有的极化性，表现出超出其他烷基膦的意外电子释放特性，并落在以 N-杂环卡宾为主的范围内。在低 Pd 负载下氯（杂）芳烃（40 个例子）的 Suzuki-Miyaura 交叉偶联过程中，PAd3 还具有显着的催化作用，包括商业药物的后期功能化。从氯芳烃合成缬沙坦和啶酰菌胺的工业前体在 10 分钟内具有 ~2 × 10(4) 周转率，证明了卓越的时空产率。
• [EN] TRI-(ADAMANTYL)PHOSPHINES AND APPLICATIONS THEREOF<br/>[FR] TRI-(ADAMANTYL)PHOSPHINES ET LEURS APPLICATIONS
  申请人：UNIV PRINCETON

  公开号：WO2017075581A1

  公开（公告）日：2017-05-04

  In one aspect, phosphine compounds comprising three adamantyl moieties (PAd3) and associated synthetic routes are described herein. Each adamantyl moiety may be the same or different. For example, each adamantyl moiety (Ad) attached to the phosphorus atom can be independently selected from the group consisting of adamantane, diamantane, triamantane and derivatives thereof. Transition metal complexes comprising PAd3 ligands are also provided for catalytic synthesis including catalytic cross-coupling reactions.

  在一个方面，本文描述了包括三个金刚烷基团（PAd3）的膦化合物及其相关的合成途径。每个金刚烷基团可以相同也可以不同。例如，连接到磷原子的每个金刚烷基团（Ad）可以独立地从金刚烷、二金刚烷、三金刚烷及其衍生物组成的群体中选择。还提供了包括PAd3配体的过渡金属配合物，用于催化合成，包括催化交叉偶联反应。
• Slow Release of Organoboronic Acids in Cross-Coupling Reactions
  申请人：Burke Martin D.

  公开号：US20100121062A1

  公开（公告）日：2010-05-13

  A method of performing a chemical reaction includes reacting a compound selected from the group consisting of an organohalide and an organo-pseudohalide, and a protected organoboronic acid represented by formula (I) in a reaction mixture: R 1 —B-T   (I); where R 1 represents an organic group, T represents a conformationally rigid protecting group, and B represents boron having sp 3 hybridization. When unprotected, the corresponding organoboronic acid is unstable by the boronic acid neat stability test. The reaction mixture further includes a base having a pK B of at least 1 and a palladium catalyst. The method further includes forming a cross-coupled product in the reaction mixture.

  一种化学反应的方法包括在反应混合物中反应从有机卤化物和有机伪卤化物中选择的化合物，以及由公式（I）表示的受保护的有机硼酸：R1—B-T  （I）;其中，R1表示有机基团，T表示构象刚性保护基团，B表示具有sp3杂化的硼。当未受保护时，相应的有机硼酸在硼酸稳定性测试中不稳定。反应混合物还包括具有至少1的pKB值和钯催化剂的碱。该方法还包括在反应混合物中形成交叉偶联产物。
• Tri-(adamantyl)phosphines and applications thereof
  申请人：The Trustees of Princeton University

  公开号：US10981157B2

  公开（公告）日：2021-04-20

  In one aspect, phosphine compounds comprising three adamantyl moieties (PAd3) and associated synthetic routes are described herein. Each adamantyl moiety may be the same or different. For example, each adamantyl moiety (Ad) attached to the phosphorus atom can be independently selected from the group consisting of adamantane, diamantane, triamantane and derivatives thereof. Transition metal complexes comprising PAd3 ligands are also provided for catalytic synthesis including catalytic cross-coupling reactions.

  一方面，本文描述了包含三个金刚烷基的膦化合物（PAd3）及相关合成路线。每个金刚烷基分子可以相同，也可以不同。例如，连接到磷原子上的每个金刚烷基（Ad）可以独立地选自金刚烷、二金刚烷、三金刚烷及其衍生物组成的组。包含 PAd3 配体的过渡金属配合物还可用于催化合成，包括催化交叉偶联反应。
• TRI-(ADAMANTYL)PHOSPHINES AND APPLICATIONS THEREOF
  申请人：The Trustees of Princeton University

  公开号：US20210162389A1

  公开（公告）日：2021-06-03

  In one aspect, phosphine compounds comprising three adamantyl moieties (PAd 3 ) and associated synthetic routes are described herein. Each adamantyl moiety may be the same or different. For example, each adamantyl moiety (Ad) attached to the phosphorus atom can be independently selected from the group consisting of adamantane, diamantane, triamantane and derivatives thereof. Transition metal complexes comprising PAd 3 ligands are also provided for catalytic synthesis including catalytic cross-coupling reactions.