2′-(4-chlorobenzoyl)acetophenone | 244640-37-7

• 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′-(4-chlorobenzoyl)acetophenone
• 英文别名: 1-[2-(4-chlorobenzoyl)phenyl]ethanone
• CAS: 244640-37-7
• 化学式: C₁₅H₁₁ClO₂
• 分子量: 258.704
• InChiKey: XQSVWNZICKXCTM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2′-(4-chlorobenzoyl)acetophenone 在 水 、 sodium hydroxide 作用下， 以 二甲基亚砜 为溶剂， 反应 6.0h， 以76%的产率得到7-chloro-13b-(4-chlorophenyl)benzo[a]indeno[1,2-c]fluorene-9,14(8bH,13bH)-dione
  参考文献：
  名称：

  Regioselective quadruple domino aldolization/aldol condensation/Michael/SNAr-cyclization: construction of hexacyclic indeno-fused C-nor-D-homo-steroid frameworks

  摘要：

  An operationally simple and highly atom-economic anionic quadruple domino reaction sequence for the synthesis of hexacyclic indeno-fused naphthalene/quinoline molecules having structural resemblance with the C-nor-D-homo-steroid nucleus has been developed. Promoter and solvent specificity, regioselectivity and mechanistic details were experimentally established. Catalyst concentration and solvent dependent switching of domino steps creating four new C-C bonds are discussed. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.01.059
• 作为产物：
  描述：

  4-氯苯基溴化镁 在 N-碘代丁二酰亚胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 水 为溶剂， 反应 39.0h， 生成 2′-(4-chlorobenzoyl)acetophenone
  参考文献：
  名称：

  碘促进o-乙烯基二芳基酮氧化转化为o-乙酰二芳基酮，合成作为鬼臼毒素类似物的1-甲基-4-芳基酞嗪

  摘要：

  描述了一种在分子碘或 N-碘代琥珀酰亚胺存在下无金属氧化邻乙烯基二芳基酮以得到邻乙酰基二芳基酮的新方法。这种转变涉及碘醇的初始形成，碘醇的邻羰基参与随后的重排以得到邻乙酰基二芳基酮。邻羰基的存在和参与是成功转化所必需的。设想的 1-甲基-4-芳基酞嗪由这些邻乙酰二芳基酮合成，并研究了它们对哺乳动物细胞系的抗增殖活性。

  DOI：

  10.1002/ejoc.201301159

文献信息

• Palladium-Catalyzed Direct Oxidative Coupling of Iodoarenes with Primary Alcohols Leading to Ketones: Application to the Synthesis of Benzofuranones and Indenones
  作者：Basuli Suchand、Chinnabattigalla Sreenivasulu、Gedu Satyanarayana

  DOI：10.1002/ejoc.201900769

  日期：2019.8.15

  investigated, utilizing readily available primary alcohols as acylating sources. Overall, this oxidative coupling proceeds via three distinct transformations such as oxidation, radical formation, and cross-coupling in one catalytic process. This protocol does not involve the assistance of a directing group or activation of the carbonyl group by any other means. Furthermore, this reaction made use of no

  在本研究中，利用容易获得的伯醇作为酰化源，研究了通过交叉脱氢偶联进行钯催化的直接氧化酰化。总体而言，这种氧化偶联通过三种不同的转化进行，例如氧化、自由基形成和一个催化过程中的交叉偶联。该协议不涉及导向基团的协助或通过任何其他方式激活羰基。此外，该反应没有使用有毒的一氧化碳气体作为羰基化剂；相反，原料伯醇已被用作酰化源。值得注意的是，可以合成苯并呋喃酮和茚酮。该策略也适用于正丁基苯酞、非诺贝特、吡托苯酮和新木脂素的合成。
• Pd-Catalyzed <i>Ortho</i>-C−H Acylation/Cross Coupling of Aryl Ketone <i>O</i>-Methyl Oximes with Aldehydes Using <i>tert</i>-Butyl Hydroperoxide as Oxidant
  作者：Chun-Wo Chan、Zhongyuan Zhou、Albert S. C. Chan、Wing-Yiu Yu

  DOI：10.1021/ol101618u

  日期：2010.9.3

  Pd-catalyzed protocol for direct C−H bond acylation by cross coupling of aryl ketone oximes and aldehydes using tert-butyl hydroperoxide (TBHP) as oxidant was developed. With oximes as a directing group for the C−H activation, the coupling with aldehydes was achieved with remarkable regioselectivity. The acylation reactions exhibit excellent functional group tolerance, and both aliphatic and heteroaromatic

  开发了一种钯催化的方案，该方案通过使用叔丁基氢过氧化物（TBHP）作为氧化剂，通过芳基酮肟和醛的交叉偶联来直接进行CH键的酰化反应。用肟作为CH活化的指导基团，与醛的偶联具有显着的区域选择性。酰化反应显示出优异的官能团耐受性，并且脂族和杂芳族醛都可以有效地与肟偶联。
• Iodine-Promoted Oxidative Conversion of<i>o</i>-Vinyl Diaryl Ketones into<i>o</i>-Acetyl Diaryl Ketones, Synthesis of 1-Methyl-4-arylphthalazines as Analogues of Podophyllotoxin
  作者：Kommidi Harikrishna、Ramesh Mukkamala、Bettina Hinkelmann、Florenz Sasse、Indrapal Singh Aidhen

  DOI：10.1002/ejoc.201301159

  日期：2014.2

  method is described for the metal-free oxidation of o-vinyl diaryl ketones in the presence of molecular iodine or N-iodosuccinimide to give o-acetyl diaryl ketones. This transformation involves the initial formation of an iodohydrin, and the o-carbonyl group of the iodohydrin participates in a subsequent rearrangement to give the o-acetyl diaryl ketone. The presence and participation of ortho-carbonyl

  描述了一种在分子碘或 N-碘代琥珀酰亚胺存在下无金属氧化邻乙烯基二芳基酮以得到邻乙酰基二芳基酮的新方法。这种转变涉及碘醇的初始形成，碘醇的邻羰基参与随后的重排以得到邻乙酰基二芳基酮。邻羰基的存在和参与是成功转化所必需的。设想的 1-甲基-4-芳基酞嗪由这些邻乙酰二芳基酮合成，并研究了它们对哺乳动物细胞系的抗增殖活性。
• Regioselective quadruple domino aldolization/aldol condensation/Michael/SNAr-cyclization: construction of hexacyclic indeno-fused C-nor-D-homo-steroid frameworks
  作者：Tanmoy Chanda、Sushobhan Chowdhury、B. Janaki Ramulu、Suvajit Koley、Raymond C.F. Jones、Maya Shankar Singh

  DOI：10.1016/j.tet.2014.01.059

  日期：2014.3

  An operationally simple and highly atom-economic anionic quadruple domino reaction sequence for the synthesis of hexacyclic indeno-fused naphthalene/quinoline molecules having structural resemblance with the C-nor-D-homo-steroid nucleus has been developed. Promoter and solvent specificity, regioselectivity and mechanistic details were experimentally established. Catalyst concentration and solvent dependent switching of domino steps creating four new C-C bonds are discussed. (C) 2014 Elsevier Ltd. All rights reserved.