2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)anthracene-9,10-dione | 867306-40-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)anthracene-9,10-dione
• CAS: 867306-40-9
• 化学式: C₁₉H₁₇BO₄
• 分子量: 320.153
• InChiKey: CKGPEKGUJSOERU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.23
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)anthracene-9,10-dione 在 sodium hydroxide 、 双氧水 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 以77%的产率得到2-羟基蒽醌
  参考文献：
  名称：

  Synthesis of arylboronates via Cp*RuCl-catalyzed cycloaddition of alkynylboronates

  摘要：

  In the presence of 5-10 mol% Cp*RuCI(cod), 1,6- and 1,7-diynes were allowed to react with an ethynylboronate at ambient temperature to give rise to bicyclic arylboronates in 64-93% isolated yields. 1,6-Diynes bearing a boronate terminal also underwent cycloaddition with monoalkynes to give the corresponding bicyclic arylboronates. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.02.068
• 作为产物：
  描述：

  2, 2, 5, 5, 8, 8-hexamethyl-3, 7-dioxa-2, 8-disilanonane 在 chloro(1,5-cyclooctadiene)(pentamethylcyclopentadiene)ruthenium(II) 三甲基氯硅烷 作用下， 以 1,2-二氯乙烷 、 丙酮 为溶剂， 反应 25.0h， 生成 2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)anthracene-9,10-dione
  参考文献：
  名称：

  Synthesis of arylboronates via Cp*RuCl-catalyzed cycloaddition of alkynylboronates

  摘要：

  In the presence of 5-10 mol% Cp*RuCI(cod), 1,6- and 1,7-diynes were allowed to react with an ethynylboronate at ambient temperature to give rise to bicyclic arylboronates in 64-93% isolated yields. 1,6-Diynes bearing a boronate terminal also underwent cycloaddition with monoalkynes to give the corresponding bicyclic arylboronates. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.02.068

文献信息

• Synthesis of bi- and tricyclic arylboronates via Cp*RuCl-catalyzed cycloaddition of α,ω-diynes with ethynylboronate
  作者：Yoshihiko Yamamoto、Kozo Hattori、Jun-ichi Ishii、Hisao Nishiyama、Kenji Itoh

  DOI：10.1039/b506977g

  日期：——

  In the presence of 5–10 mol% Cp*RuCl(cod), 1,6- and 1,7-diynes were allowed to react with an ethynylboronate at ambient temperature to give rise to bi- and tricyclic arylboronates in 64–93% isolated yields.

  在存在5-10摩尔%的Cp*RuCl(cod)的情况下，1,6-和1,7-二炔与乙炔基硼酸盐在常温下反应，以64-93%的分离产率产生了双环和三环芳基硼酸盐。
• Decarbonylative Fluoroalkylation at Palladium(II): From Fundamental Organometallic Studies to Catalysis
  作者：Naish Lalloo、Christian A. Malapit、S. Maryamdokht Taimoory、Conor E. Brigham、Melanie S. Sanford

  DOI：10.1021/jacs.1c08551

  日期：2021.11.10

  acid-derived electrophiles [RFC(O)X] with aryl organometallics (Ar–M′). This reaction was optimized by interrogating the individual steps of the catalytic cycle (oxidative addition, carbonyl de-insertion, transmetalation, and reductive elimination) to identify a compatible pair of coupling partners and an appropriate Pd catalyst. These stoichiometric organometallic studies revealed several critical elements

  本文介绍了脱羰基 Pd 催化的芳基-氟烷基成键反应的发展，该反应将氟烷基羧酸衍生的亲电子试剂 [ RF C (O)X] 与芳基有机金属化合物 (Ar-M') 偶联。通过询问催化循环的各个步骤（氧化加成、羰基脱插入、金属转移和还原消除）来优化该反应，以确定一对相容的偶联伙伴和合适的 Pd 催化剂。这些化学计量有机金属研究揭示了反应设计的几个关键要素。首先，使用 M' = 硼酸酯可以避免R F C(O)X 和 Ar–M'之间未催化的背景反应。二、羰基脱嵌和Ar-R F当 R F = CF 3时，还原消除是催化循环中最慢的两个步骤。更改为 R F = CHF 2后，这两个步骤都会显着加快。计算研究表明，有利的 F 2 C–H---X 相互作用有助于加速该系统中的羰基脱嵌。最后，X = 二氟乙酸盐的金属转移速度较慢，但​​ X = F 的金属转移速度较快。最终，这些研究促成了 (SPhos)Pd
• Synthesis and electrochemical studies of an anthraquinone-conjugated nucleoside and derived oligonucleotides
  作者：Mikkel F. Jacobsen、Elena E. Ferapontova、Kurt V. Gothelf

  DOI：10.1039/b816820b

  日期：——

  The synthesis of a 2′-deoxyuridine nucleoside linked to an anthraquinone moiety, and its incorporation into oligonucleotides are described, including a facile oxidative demethylation with phenyliodine(III) bis(trifluoroacetate) to reveal the anthraquinone motif. Furthermore, some useful physical and electrochemical properties of the obtained oligonucleotide are also reported, which allow its principal

  描述了与蒽醌部分连接的2'-脱氧尿苷核苷的合成及其掺入寡核苷酸的过程，包括容易进行的氧化脱甲基 苯碘（III）双（三氟乙酸盐）揭示蒽醌基序。此外，还报道了所获得的寡核苷酸的一些有用的物理和电化学性质，这使其可以主要用于电化学DNA测定中。
• Synthesis of arylboronates via Cp*RuCl-catalyzed cycloaddition of alkynylboronates
  作者：Yoshihiko Yamamoto、Kozo Hattori、Jun-ichi Ishii、Hisao Nishiyama

  DOI：10.1016/j.tet.2006.02.068

  日期：2006.5

  In the presence of 5-10 mol% Cp*RuCI(cod), 1,6- and 1,7-diynes were allowed to react with an ethynylboronate at ambient temperature to give rise to bicyclic arylboronates in 64-93% isolated yields. 1,6-Diynes bearing a boronate terminal also underwent cycloaddition with monoalkynes to give the corresponding bicyclic arylboronates. (c) 2006 Elsevier Ltd. All rights reserved.