(E)-2-(2-methoxybenzylidene)cyclopentan-1-one | 134791-41-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (E)-2-(2-methoxybenzylidene)cyclopentan-1-one
• 英文别名: E-2-(2-methoxybenzylidene)cyclopentanone；2-(E)-[(2-methoxy) benzylidene]cyclopentanone；(2E)-2-[(2-methoxyphenyl)methylidene]cyclopentan-1-one
• CAS: 134791-41-6
• 化学式: C₁₃H₁₄O₂
• 分子量: 202.253
• InChiKey: UQFVAGXCGYNBRC-MDZDMXLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 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：

  (E)-2-(2-methoxybenzylidene)cyclopentan-1-one 在 甲酸 、 (R)-Ru(η6-mesitylene)-(R,R)-TsDPEN 、 三乙胺 作用下， 以 氯仿 为溶剂， 反应 6.0h， 以77%的产率得到(S, E)-2-(2-methoxybenzylidene)cyclopentanol
  参考文献：
  名称：

  钌催化的2-亚芳基环烷酮的化学选择性转移加氢合成手性环外烯丙基醇

  摘要：

  已经系统地研究了2-芳基四，五，六和七元环烷烃的C O键的排他不对称还原。在温和条件下，使用稳固且可商购的手性二胺衍生钌络合物作为催化剂，HCOOH / Et 3 N作为氢源，进行不对称转移氢化，给出了51种示例手性环外烯丙基醇，收率高达96％， 99％ee。该方法也适用于抗炎洛索洛芬和天然产物（-）-goniomitine的活性中间体的克级合成。

  DOI：

  10.1039/d1gc00026h
• 作为产物：
  描述：

  2-甲氧基苯甲醇 在 Nafion-TMS 、 polymer supported perruthenate 作用下， 以 二氯甲烷 为溶剂， 反应 88.0h， 生成 (E)-2-(2-methoxybenzylidene)cyclopentan-1-one
  参考文献：
  名称：

  Haunert, Frank; Bolli, Martin H.; Hinzen, Berthold, Journal of the Chemical Society. Perkin transactions I, 1998, # 15, p. 2235 - 2237

  摘要：

  DOI：

文献信息

• RuPHOX-Ru-Catalyzed Selective Asymmetric Hydrogenation of Exocyclic α,β-Unsaturated Pentanones
  作者：Jing Li、Yue Zhu、Yufei Lu、Yanzhao Wang、Yangang Liu、Delong Liu、Wanbin Zhang

  DOI：10.1021/acs.organomet.9b00366

  日期：2019.10.28

  A RuPHOX-Ru catalyzed selective asymmetric hydrogenation of exocyclic α,β-unsaturated ketones has been developed, furnishing the corresponding chiral exocyclic allylic alcohols in high yields and with up to >99.5% ee. The reaction could be performed on a gram scale with a relatively low catalyst loading (up to 10000 S/C) without any loss in reaction activity and enantioselectivity. The resulting hydrogenated

  已开发出RuPHOX-Ru催化的环外α，β-不饱和酮的选择性不对称氢化，可提供高收率和最高> 99.5％ee的相应手性环外烯丙基醇。该反应可以以克级进行，具有相对较低的催化剂负载量（最高10000 S / C），而没有任何反应活性和对映选择性的损失。所得的氢化产物可以容易地转化为具有高不对称性能的几种生物活性化合物。不对称方案为合成手性环外烯丙基醇提供了一种有效的方法。
• 2-(N-substituted-aminoalkyl)-5-(E)-alkylidene cyclopentanones,
  申请人：University of Pittsburgh

  公开号：US05250735A1

  公开（公告）日：1993-10-05

  Novel 2-(N-substituted-aminoalkyl)-5-(E)-alkylidene cyclopentanones, 2-(N-substituted-aminoalkyl)-5-(E)-arylalkylidene cyclopentanones, and derivatives thereof having the formula ##STR1## wherein x is methylene or ethylene; R.sub.1 is dimethylamino, diethylamino, 1-pyrrolidinyl, 1-piperidinyl, 4-morpholinyl, anilino or substituted anilino; R.sub.2 is hydrogen, straight or branched alkyl of 1 to 9 carbon atoms, aryl or arylalkyl; R.sub.3 is hydrogen, straight or branched alkyl of 1 to 9 carbon atoms, aryl or arylalkyl; and R.sub.4 is hydrogen, methyl, ethyl, allyl, benzyl, substituted benzyl, cyclopentyl, substituted cyclopentyl, cyclopenten-1-yl, or substituted cyclopenten-1-yl; and wherein aryl is phenyl or phenyl substituted with one or more methoxyl, hydroxyl, methylenedioxy, chloro, bromo, fluoro, ethoxycarbonylmethoxy, benzoxy, alkyl group, or their combination, possess anti-inflammatory, analgesic and anticancer properties. The methods of using these compounds to treat inflammation, pain and cancer in mammals and to resist or substantially prevent inflammation and pain in mammals are also disclosed.

  2-(N-取代氨基烷基)-5-(E)-取代芳基烷基亚甲基环戊酮，2-(N-取代氨基烷基)-5-(E)-芳基烷基亚甲基环戊酮及其衍生物，其化学式为：##STR1## 其中x为亚甲基或乙烯基；R.sub.1为二甲氨基，二乙氨基，1-吡咯烷基，1-哌啶基，4-吗啉基，苯胺基或取代苯胺基；R.sub.2为氢，直链或支链烷基，长度为1到9个碳原子，芳基或芳基烷基；R.sub.3为氢，直链或支链烷基，长度为1到9个碳原子，芳基或芳基烷基；R.sub.4为氢，甲基，乙基，烯丙基，苄基，取代苄基，环戊基，取代环戊基，环戊-1-烯基或取代环戊-1-烯基；其中芳基为苯基或经过一个或多个甲氧基，羟基，亚甲基二氧基，氯，溴，氟，乙氧羰基甲氧基，苯氧基，烷基或其组合取代的苯基。这些化合物具有抗炎，镇痛和抗癌特性。本文还公开了使用这些化合物治疗哺乳动物的炎症，疼痛和癌症以及抵抗或显著预防哺乳动物炎症和疼痛的方法。
• Method of treating inflammation and pain with
  申请人：University of Pittsburgh of the Commonwealth System of Higher Education

  公开号：US05281622A1

  公开（公告）日：1994-01-25

  Novel 2-(N-substituted-aminoalkyl)-5-(E)-alkylidene cyclopentanones, 2-(N-substituted-aminoalkyl)-5-(E)-arylalkylidene cyclopentanones, and derivatives thereof having the formula ##STR1## wherein x is methylene or ethylene; R.sub.1 is dimethylamino, diethylamino, 1-pyrrolidinyl, 1-piperidinyl, 4-morpholinyl, anilino or substituted anilino; R.sub.2 is hydrogen, straight or branched alkyl of 1 to 9 carbon atoms, aryl or arylalkyl; R.sub.3 is hydrogen, straight or branched alkyl of 1 to 9 carbon atoms, aryl or arylalkyl; and R.sub.4 is hydrogen, methyl, ethyl, allyl, benzyl, substituted benzyl, cyclopentyl, substituted cyclopentyl, cyclopenten-1-yl, or substituted cyclopenten-1-yl; and wherein aryl is phenyl or phenyl substituted with one or more methoxyl, hydroxyl, methylenedioxy, chloro, bromo, fluoro, ethoxycarbonylmethoxy, benzoxy, alkyl group, or their combination, possess anti-inflammatory, analgesic and anticancer properties. The methods of using these compounds to treat inflammation, pain and cancer in mammals and to resist or substantially prevent inflammation and pain in mammals are also disclosed.

  第二类小说-2-(N-取代氨基烷基)-5-(E)-取代烷基环戊酮，2-(N-取代氨基烷基)-5-(E)-芳基烷基环戊酮及其衍生物，其化学式为##STR1## 其中x为亚甲基或乙烯基; R.sub.1为二甲氨基，二乙氨基，1-吡咯啉基，1-哌啶基，4-吗啉基，苯胺基或取代苯胺基; R.sub.2为氢，1至9个碳原子的直链或支链烷基，芳基或芳基烷基; R.sub.3为氢，1至9个碳原子的直链或支链烷基，芳基或芳基烷基; R.sub.4为氢，甲基，乙基，烯丙基，苄基，取代苄基，环戊基，取代环戊基，环戊烯-1-基或取代环戊烯-1-基; 其中芳基为苯基或取代苯基，取代基包括一个或多个甲氧基，羟基，亚甲基二氧基，氯，溴，氟，乙氧羰甲氧基，苯氧基，烷基或它们的组合，具有抗炎，镇痛和抗癌特性。还公开了使用这些化合物治疗哺乳动物的炎症，疼痛和癌症，并抵抗或显著预防哺乳动物的炎症和疼痛的方法。
• Copper‐Catalyzed Chemoselective Asymmetric Hydrogenation of C=O Bonds of Exocyclic α,β‐Unsaturated Pentanones
  作者：Jing Guan、Jianzhong Chen、Yicong Luo、Lisen Guo、Wanbin Zhang

  DOI：10.1002/anie.202306380

  日期：2023.8.28

  An earth-abundant transition-metal copper catalyzed asymmetric hydrogenation of exocyclic α,β-unsaturated pentanones affording the corresponding chiral exocyclic allylic pentanols in up to 99 % yield and 96 % ee (enantiomeric excess) is reported. Mechanistic studies indicate that only the C=O bond is chemoselectively reduced and the reaction is promoted via the multiple attractive dispersion interactions

  据报道，地球丰富的过渡金属铜催化环外 α,β-不饱和戊酮的不对称氢化，得到相应的手性环外烯丙基戊醇，收率高达 99%，ee（对映体过量）为 96%。机理研究表明，只有 C=O 键被化学选择性还原，并且通过 Cu 催化剂和底物之间的多重吸引分散相互作用促进反应。
• Direct Preparation of Monoarylidene Derivatives of Aldehydes and Enolizable Ketones with DIMCARB
  作者：Ulf P. Kreher、Anthony E. Rosamilia、Colin L. Raston、Janet L. Scott、Christopher R. Strauss

  DOI：10.1021/ol0351145

  日期：2003.8.1

  Aryl alpha,beta-unsaturated ketones and aldehydes were synthesized, in moderate to excellent yields, with use of dimethylammonium dimethyl carbamate (DIMCARB) as a recyclable reaction medium and as a catalyst.