(S)-3-ethyl-2,3-dihydro-1H-inden-1-one | 22573-42-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: (S)-3-ethyl-2,3-dihydro-1H-inden-1-one
• 英文别名: (3S)-3-ethyl-2,3-dihydroinden-1-one
• CAS: 22573-42-8
• 化学式: C₁₁H₁₂O
• 分子量: 160.216
• InChiKey: KNUNPFLGVSVQQF-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (S)-3-ethyl-2,3-dihydro-1H-inden-1-one 在 三氟过氧乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以75%的产率得到(S)-4-ethylchroman-2-one
  参考文献：
  名称：

  Preparation of chiral indanones and dihydrocoumarins; application to synthesis of (+)-3-(2,6-dimethoxyphenyl) pentanoic acid

  摘要：

  Chiral beta-aryl carboxylic acids, prepared by Michael addition of organocuprates to chiral unsaturated imides, are transformed into chiral 3-alkyl-4-benzoyloxyindan-1-ones via two intramolecular acylations, with intermediate formation of chiral 3-alkylindanones and corresponding dihydrocoumarins. The 3-(S)-ethyl-4-benzoyloxyindanone is transformed into(+)-3-(S)-(2,6-dimethoxyphenyl)pentanoic acid.

  DOI：

  10.1016/s0957-4166(00)80481-4
• 作为产物：
  描述：

  (4R,5S)-1,5-dimethyl-3-[(E)-pent-2-enoyl]-4-phenylimidazolidin-2-one 在 lithium hydroxide 、 三氯化铝 、 草酰氯 、 copper(I) bromide 作用下， 生成 (S)-3-ethyl-2,3-dihydro-1H-inden-1-one
  参考文献：
  名称：

  Preparation of chiral indanones and dihydrocoumarins; application to synthesis of (+)-3-(2,6-dimethoxyphenyl) pentanoic acid

  摘要：

  Chiral beta-aryl carboxylic acids, prepared by Michael addition of organocuprates to chiral unsaturated imides, are transformed into chiral 3-alkyl-4-benzoyloxyindan-1-ones via two intramolecular acylations, with intermediate formation of chiral 3-alkylindanones and corresponding dihydrocoumarins. The 3-(S)-ethyl-4-benzoyloxyindanone is transformed into(+)-3-(S)-(2,6-dimethoxyphenyl)pentanoic acid.

  DOI：

  10.1016/s0957-4166(00)80481-4

文献信息

• Ir-catalyzed asymmetric hydrogenation of 3-arylindenones for the synthesis of chiral 3-arylindanones
  作者：Jun Yan、Yu Nie、Feng Gao、Qianjia Yuan、Fang Xie、Wanbin Zhang

  DOI：10.1016/j.tet.2021.132003

  日期：2021.3

  An efficient synthesis of chiral 3-arylindanones via iridium-catalyzed asymmetric hydrogenation of 3-arylindenones has been developed. The reaction showed good compatibility with various functional groups, delivering a variety of 3-arylindanones in excellent yields and with good enantioselectivities. The reaction was also carried out on a gram-scale, delivering the product in quantitative yield. In

  已经开发了通过铱催化的3-炔烃的不对称氢化的有效合成手性3-芳基茚满酮。该反应显示出与各种官能团的良好相容性，以优异的产率和良好的对映选择性提供了各种3-芳基茚满酮。该反应也以克为单位进行，以定量产率递送产物。此外，产品可以轻松衍生化并转化为天然产品和药物制剂。
• Cobalt-Catalyzed Enantioselective Intramolecular Hydroacylation of Ketones and Olefins
  作者：Junfeng Yang、Naohiko Yoshikai

  DOI：10.1021/ja509919x

  日期：2014.12.3

  Cobalt-chiral diphoshine catalytic systems promote intramolecular hydroacylation reactions of 2-acylbenzaldehydes and 2-alkenylbenzaldehydes to afford phthalide and indanone derivatives, respectively, in moderate to good yields with high enantioselectivities. The ketone hydroacylation did not exhibit a significant H/D kinetic isotope effect (KIE) with respect to the aldehyde C-H bond, indicating that C-H activation would not be involved in the rate-limiting step.
• Catalytic Enantioselective Negishi Reactions of Racemic Secondary Benzylic Halides
  作者：Forrest O. Arp、Gregory C. Fu

  DOI：10.1021/ja053751f

  日期：2005.8.1

  This report describes the first enantioselective cross-couplings of racemic secondary benzylic halides, specifically, nickel-catalyzed Negishi reactions of bromides and chlorides. The catalyst components are commercially available and air-stable, and the reaction is not highly oxygen- or moisture-sensitive (it can be set up in the air). The method has been applied to the catalytic enantioselective synthesis of intermediates employed by others in the generation of bioactive compounds (e.g., trikentrin A and an androgen receptor agonist).
• A Rotary Molecular Motor Gated by Electrical Energy
  作者：Chen-Yi Kao、Hsiu-Feng Lu、Ito Chao、Jye-Shane Yang

  DOI：10.1021/ol502946v

  日期：2014.12.5

  DFT calculations predict that the chiral pentiptycene derivative E-1 possesses distinct rotational potential energy surfaces in the neutral vs the radical anionic (E-1(center dot-)) form such that continued electrochemical switching between E-1 and E-1(center dot-) could lead to a directional rotation of the pentiptycene rotor about the exocyclic C-C bond. The time scale of random Brownian rotation is similar to 10(6) s for E-1 and similar to 170 s for E-1(center dot-) at 150 K, and thus a switching time scale of 0.2 s could readily bias the rotation direction to >99% at 150 K. The synthetic feasibility, line-shape analysis on the VT 1H NMR spectra, and electrochemical redox switching of E-1 are demonstrated.
• Preparation of chiral indanones and dihydrocoumarins; application to synthesis of (+)-3-(2,6-dimethoxyphenyl) pentanoic acid
  作者：Elie Stephan、Richard Rocher、Jeaninc Aubouet、Guy Pourcelot、Pierre Cresson

  DOI：10.1016/s0957-4166(00)80481-4

  日期：1994.1

  Chiral beta-aryl carboxylic acids, prepared by Michael addition of organocuprates to chiral unsaturated imides, are transformed into chiral 3-alkyl-4-benzoyloxyindan-1-ones via two intramolecular acylations, with intermediate formation of chiral 3-alkylindanones and corresponding dihydrocoumarins. The 3-(S)-ethyl-4-benzoyloxyindanone is transformed into(+)-3-(S)-(2,6-dimethoxyphenyl)pentanoic acid.