6-methoxy-2-methylene-2,3-dihydro-1H-inden-1-one | 193806-87-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 6-methoxy-2-methylene-2,3-dihydro-1H-inden-1-one
• 英文别名: 6-methoxy-2-methylidene-3H-inden-1-one
• CAS: 193806-87-0
• 化学式: C₁₁H₁₀O₂
• 分子量: 174.199
• InChiKey: MPIVMPQINLNFLF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,4,6-三甲基苯甲腈N-氧化物 、 6-methoxy-2-methylene-2,3-dihydro-1H-inden-1-one 以 二氯甲烷 为溶剂， 反应 8.0h， 以85%的产率得到6-methoxy-3'-(2,4,6-trimethylphenyl)spiro[3H-indene-2,5'-4H-1,2-oxazole]-1-one
  参考文献：
  名称：

  腈与 α-亚甲基环酮的 1,3-偶极环加成反应合成新型螺异恶唑啉

  摘要：

  在苯甲腈与不同的 α-亚甲基环酮的高度区域选择性环加成反应中，以良好的收率制备了新型螺异恶唑啉。

  DOI：

  10.1080/00397919908086046
• 作为产物：
  描述：

  6-甲氧基-1-茚酮 在 silica gel 作用下， 以 甲醇 、 氯仿 、 乙腈 为溶剂， 反应 2.0h， 生成 6-methoxy-2-methylene-2,3-dihydro-1H-inden-1-one
  参考文献：
  名称：

  β-氨基酮作为1型甲硫氨酸氨基肽酶选择性不可逆抑制剂的前药

  摘要：

  我们鉴定并表征了β-氨基酮作为不可逆MetAP抑制剂的前药，这些抑制剂对MetAP-1亚型具有选择性。具有某些结构特征的β-氨基酮在生理条件下会形成α，β-不饱和酮，这些酮共价且选择性地与MetAP-1 S1口袋中的半胱氨酸结合。通过X射线晶体学和用来自大肠杆菌，金黄色葡萄球菌和两种人同工型的MetAP的测定证实了结合模式。最初鉴定的四氢萘酮衍生物对大肠杆菌MetAP相对于人MetAP-1和MetAP-2具有完全的选择性。茚满酮类似物的合理设计产生对人类1型与人类2 MetAP具有选择性的化合物。

  DOI：

  10.1016/j.bmcl.2014.09.047

文献信息

• Direct Carbocyclizations of Benzoic Acids: Catalyst-Controlled Synthesis of Cyclic Ketones and the Development of Tandem aHH (acyl Heck-Heck) Reactions
  作者：Kelsey C. Miles、Chi “Chip” Le、James P. Stambuli

  DOI：10.1002/chem.201403561

  日期：2014.9.1

  The formation of exo‐methylene indanones and indenones from simple ortho‐allyl benzoic acid derivatives has been developed. Selective formation of the indanone or indenone products in these reactions is controlled by choice of ancillary ligand. This new process has a low environmental footprint as the products are formed in high yields using low catalyst loadings, while the only stoichiometric chemical

  已经开发了由简单的邻烯丙基苯甲酸衍生物形成外亚甲基茚满酮和茚满的现象。在这些反应中茚满酮或茚满酮产物的选择性形成是通过选择辅助配体来控制的。这种新工艺具有较低的环境足迹，因为使用低催化剂负载量可以高收率形成产物，而转化中反应物产生的唯一化学计量的化学废物是乙酸。活性环化催化剂向Hermman-Beller palladacycle的转化被用于一锅串联的酰基Heck-Heck（aHH）反应中，并用于多奈哌齐的合成。
• Copper-catalysed oxidative Csp³–H methylenation to terminal olefins using DMF
  作者：Jianming Liu、Hong Yi、Xin Zhang、Chao Liu、Ren Liu、Guoting Zhang、Aiwen Lei

  DOI：10.1039/c4cc02275k

  日期：——

  A copper-catalysed direct oxidative Csp(3)-H methylenation to terminal olefins using DMF as one carbon source was developed. In this reaction, various functional groups were well tolerated, thus providing a simple way to construct arylvinylketones and arylvinylpyridines. The preliminary mechanistic investigations revealed that CH2 was from DMF (N-CH3).

  铜催化的直接氧化Csp（3）-H亚甲基化为使用DMF作为一种碳源的末端烯烃。在该反应中，各种官能团被很好地耐受，因此提供了构建芳基乙烯基酮和芳基乙烯基吡啶的简单方法。初步的机械研究表明，CH2来自DMF（N-CH3）。
• Selectfluor-promoted α-methylenation of aromatic ketones to terminal olefins using acetonitrile as one carbon source
  作者：Zhiqi Liu、Yuan Zhang、Weibin Fan、Deguang Huang

  DOI：10.1016/j.tetlet.2022.154179

  日期：2022.11

  A mehtod for the synthesis of terminal olefins by α-methylenation of aromatic ketones is reported. The reaction was carried out in air using acetonitrile as one carbon source and Selectfluor as a mild oxidant. The scope and versatility of the method were demonstrated with 29 examples. A Selectfluor-promoted oxidative reaction mechanism is proposed based on the experimental results.

  报道了一种通过芳族酮的α-亚甲基化合成末端烯烃的方法。该反应在空气中进行，使用乙腈作为一种碳源，Selectfluor 作为一种温和的氧化剂。该方法的范围和多功能性通过 29 个示例进行了展示。基于实验结果，提出了一种 Selectfluor 促进的氧化反应机理。
• Generation and Cyclization of Acyl Radicals from Thiol Esters Under Nonreducing, Tin-Free Conditions
  作者：David Crich、Xiaolin Hao

  DOI：10.1021/jo970500j

  日期：1997.8.1

  The preparation of 2-(2-((tert-butyloxycarbonyl)amino)phenyl)ethyl mercaptan from 2-(2-amino-phenyl)ethanol is described. This thiol is condensed with a series of suitably unsaturated carboxylic acids to give a series of thiol esters. The Boc group is removed and the amine reacted with isoamyl nitrite to give a series of diazonium salts. Exposure to iodide in acetone solution then generates the aryl radical, which undergoes intramolecular homolytic substitution at sulfur with liberation of the acylradical. Following acyl radical cyclization, quenching by iodine and then elimination of HI leads to the isolation of alpha-methylene cycloalkanones in good yield.
• Aminoisoxazoline Compounds as Agonists of Alpha7-Nicotinic Acetylcholine Receptors
  申请人：Forum Pharmaceuticals, Inc.

  公开号：US20170247393A1

  公开（公告）日：2017-08-31

  The present invention relates to novel aminoisoxazoline compounds, and pharmaceutical compositions of the same, that are suitable as agonists or partial agonists of α7-nAChR, and methods of preparing these compounds and compositions, and the use of these compounds and compositions in methods of maintaining, treating and/or improving cognitive function. In particular, methods of administering the compound or composition to a patient in need thereof, for example a patient with a cognitive deficiency and/or a desire to enhance cognitive function, that may derive a benefit therefrom.