α-cyclopentyl-4'-methoxyacetophenone | 24188-99-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: α-cyclopentyl-4'-methoxyacetophenone
• 英文别名: alpha-Cyclopentyl-p-methoxyacetophenone；2-cyclopentyl-1-(4-methoxyphenyl)ethanone
• CAS: 24188-99-6
• 化学式: C₁₄H₁₈O₂
• 分子量: 218.296
• InChiKey: RUQFYHVGADABLL-UHFFFAOYSA-N

物化性质

• 熔点：
  30-31 °C
• 沸点：
  157-158 °C(Press: 2 Torr)
• 密度：
  1.040±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  α-cyclopentyl-4'-methoxyacetophenone 在 三乙基硅烷 、 偶氮二甲酸二异丙酯 、 四丁基氟化铵 、 吡啶盐酸盐 、 ammonium formate 、 phenyltrimethylammonium tribromide 、 sodium hydride 、 钯 、 溶剂黄146 、 N,N-二异丙基乙胺 、 三苯基膦 、 三氟乙酸 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 生成 (2R,3S)-3-cyclopentyl-2-[4-(2-piperidin-1-ylethoxy)phenyl]-2,3-dihydro-1,4-benzoxathiin-6-ol
  参考文献：
  名称：

  Estrogen receptor ligands. Part 3: The SAR of dihydrobenzoxathiin SERMs

  摘要：

  A series of 3-alkyl, 3-cycloalkyl, and 3-heteroaryl dihydrobenzoxathim analogs 1 were prepared and evaluated for estrogen/anti-estrogen activity in both in vitro and in vivo models. In general, the compounds were found to exhibit a high degree of selectivity for ERalpha over ERbeta, but were less potent than the original lead compound la in the inhibition of estradiol-driven uterine proliferation. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.02.084
• 作为产物：
  描述：

  环戊基丙二酸 在 二硫化碳 、 三氯化铝 、 氯化亚砜 作用下， 生成 α-cyclopentyl-4'-methoxyacetophenone
  参考文献：
  名称：

  Moureu et al., Bulletin de la Societe Chimique de France, 1949, p. 475,478

  摘要：

  DOI：

文献信息

• Intermolecular Phosphite-Mediated Radical Desulfurative Alkene Alkylation Using Thiols
  作者：John M. Lopp、Valerie A. Schmidt

  DOI：10.1021/acs.orglett.9b03018

  日期：2019.10.4

  report herein the development of a S atom transfer process using triethyl phosphite as the S atom acceptor that allows thiols to serve as precursors of C-centered radicals. A range of functionalized and electronically unbiased alkenes including those containing common heteroatom-based functional groups readily participate in this reductive coupling. This process is driven by the exchange of relatively

  我们在此报告使用亚磷酸三乙酯作为S原子受体的S原子转移过程的发展，该过程允许硫醇充当C中心自由基的前体。包括含有常见的基于杂原子的官能团的烯烃在内的一系列官能化的和电子无偏的烯烃很容易参与该还原偶联。此过程是由相对较弱的脂肪族硫醇的S–H和C–S键交换为所形成产物的C–H，C–C和S–P键所驱动。
• Tandem Intramolecular Carbolithiation-Lithium/Zinc Transmetallation and Applications to Carbon−Carbon Bond-Forming Reactions
  作者：Miguel Yus、Rosa Ortiz

  DOI：10.1002/ejoc.200400349

  日期：2004.9

  Lithium/zinc transmetallation with the cyclic organolithium intermediate 3 (prepared by intramolecular carbolithiation of the initially formed organolithium 2) gives the corresponding organozinc intermediate 5. Copper- or palladium-promoted SN2′ reactions between compound 5 and allylic or propargylic halides, as well as arylation, vinylation, benzylation, acylation, and conjugate addition to α,β-unsaturated

  锂/锌与环状有机锂中间体 3（通过最初形成的有机锂 2 的分子内碳化反应制备）得到相应的有机锌中间体 5。铜或钯促进的化合物 5 与烯丙基或炔丙基卤化物之间的 SN2' 反应，以及芳基化、乙烯基化、苄基化、酰化和对 α,β-不饱和羰基化合物的共轭加成，提供（水解后）预期的化合物 7-15，即使在过渡金属催化下也不能直接从有机锂前体 3 中获得。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)
• Tandem intramolecular carbolithiation–transmetallation: from lithium to copper or boron chemistry
  作者：Rosa Ortiz、Miguel Yus

  DOI：10.1016/j.tet.2004.12.047

  日期：2005.2

  with eletrophiles, such as allylic or propargylic halides, acyl chlorides or α,β-unsaturated carbonyl compounds giving the expected compounds 6–10, which are not possible to be obtained directly from the organolithium 3. On the other hand, lithium/boron transmetallation affords the corresponding alkylboronic acid 11 which, after palladium-catalysed Suzuki–Miyaura cross-coupling reaction with different

  来自有机锂中间体3的锂/铜金属转移（通过无环有机锂2的分子内碳锂化获得，通过氯-锂交换生成）得到相应的有机铜中间体5。与eletrophiles，如烯丙基或炔丙基卤化物，酰基氯或α，给出预期的化合物β不饱和羰基化合物该中间体进行反应6 - 10，这是不能够直接从有机锂获得3。另一方面，锂/硼金属转移反应生成相应的烷基硼酸11在钯催化的Suzuki-Miyaura与不同的芳基溴化物进行交叉偶联反应后，预期产物12的收率适中，而相应的Ullman二元同质偶联产物是主要的副产物。
• Alkane and alkene derivatives and their use
  申请人：Farmos Group Ltd.

  公开号：US04556677A1

  公开（公告）日：1985-12-03

  The invention provides novel compounds of the formula ##STR1## wherein R.sub.1 is hydrogen, hydroxy, alkoxy of 1 to 4 carbon atoms, benzyloxy, allyloxy, 2,3-epoxypropoxy, methoxymethoxy, ethoxymethoxy, or 2,3-dihydroxypropoxy or ##STR2## wherein one of R.sub.5 and R.sub.6 is hydrogen or R.sub.5 and R.sub.6 are alkyl groups of 1-4 carbon atoms which may be the same or different, or the --NR.sub.5 R.sub.6 group stands for a nitrogen containing 5 to 7 membered heterocyclic radical and m is 1 or 2; R.sub.2 is an alkyl of 1 to 4 carbon atoms or ##STR3## wherein R.sub.7 has the same meanings as R.sub.1 except that R.sub.7 and R.sub.1 cannot simultaneously be the same; R.sub.3 is an alkyl of 2 to 4 carbon atoms, cyclopentyl or hydroxy-cyclopentyl; R.sub.4 is hydrogen or hydroxy; and n is 0 to 3, provided that when R.sub.4 is hydrogen, then R.sub.2 and R.sub.3 are not simultaneously lower alkyl containing up to 4 carbon atoms, and their non-toxic pharmaceutically acceptable acid addition salts and esters and mixtures thereof. Processes for the preparation of these compounds are described, as are novel pharmaceutical compositions of the compounds or their salts. The compounds and their non-toxic salts exhibit valuable pharmacological properties as estrogenic, anti-estrogenic, progestanic and anti-tumor activity. Certain compounds of the group are useful as chemical intermediates for the preparation of pharmaceutically active compounds of the invention.

  该发明提供了一种新型化合物，其化学式为##STR1##其中R.sub.1是氢、羟基、1至4个碳原子的烷氧基、苄氧基、烯丙氧基、2,3-环氧丙氧基、甲氧基甲氧基、乙氧基甲氧基、或2,3-二羟基丙氧基或##STR2##其中R.sub.5和R.sub.6中的一个是氢或R.sub.5和R.sub.6是1-4个碳原子的烷基基团，可以相同也可以不同，或--NR.sub.5 R.sub.6基团代表含氮的5至7成员杂环基团，m为1或2；R.sub.2是1至4个碳原子的烷基或##STR3##其中R.sub.7具有与R.sub.1相同的含义，但R.sub.7和R.sub.1不能同时相同；R.sub.3是2至4个碳原子的烷基、环戊基或羟基环戊基；R.sub.4是氢或羟基；n为0至3，但当R.sub.4为氢时，R.sub.2和R.sub.3不能同时是含有最多4个碳原子的低烷基，其非毒性药学可接受的酸盐和酯以及它们的混合物。描述了这些化合物的制备过程，以及这些化合物或它们的盐的新型药物组合物。这些化合物及其非毒性盐具有有价值的药理特性，如雌激素、抗雌激素、孕激素和抗肿瘤活性。该组中的某些化合物可用作该发明的药物活性化合物的化学中间体的制备。
• Photoredox Reaction of 2-Mercaptothiazolinium Salts with Silyl Enol Ethers
  作者：Artem A. Zemtsov、Salavat S. Ashirbaev、Vitalij V. Levin、Vladimir A. Kokorekin、Alexander A. Korlyukov、Alexander D. Dilman

  DOI：10.1021/acs.joc.9b02478

  日期：2019.12.6

  of free radicals from thiazolinium salts upon photocatalytic reduction is described. The thiazolinium salts are generated by treatment with methyl triflate of 2-mercaptothiazolines, which can be readily obtained from alkyl bromides and tosylates via a nucleophilic substitution reaction or by hydrothiolation of alkenes. Silyl enol ethers were used to trap the radicals, furnishing ketones after successive

  描述了一种在光催化还原下由噻唑啉鎓盐产生自由基的方法。噻唑啉鎓盐是通过用2-巯基噻唑啉的三氟甲磺酸甲酯处理而产生的，其可以容易地从烷基溴化物和甲苯磺酸盐经亲核取代反应或通过烯烃的氢硫醇化而获得。甲硅烷基烯醇醚用于捕获自由基，在连续的单电子氧化和消除甲硅烷基阳离子后提供酮。