ethyl 3,4-diphenylbutanoate | 72277-18-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: ethyl 3,4-diphenylbutanoate
• 英文别名: 3,4-diphenyl-butyric acid ethyl ester；3,4-Diphenyl-buttersaeure-aethylester
• CAS: 72277-18-0
• 化学式: C₁₈H₂₀O₂
• 分子量: 268.356
• InChiKey: ZGYGESVVASUPGH-UHFFFAOYSA-N

物化性质

• 沸点：
  190-195 °C(Press: 3 Torr)
• 密度：
  1.059±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 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：

  ethyl 3,4-diphenylbutanoate 在 二异丁基氢化铝 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 3.0h， 以85%的产率得到3,4-diphenylbutan-1-ol
  参考文献：
  名称：

  Structure-activity studies on benzhydrol-containing nipecotic acid and guvacine derivatives as potent, orally-active inhibitors of GABA uptake

  摘要：

  The introduction of lipophilic groups onto the ring nitrogen of nipecotic acid and guvacine, two known GABA uptake inhibitors, afforded potent, orally-active anticonvulsant drugs. A series of compounds is reported which explores the structure-activity relationships (SAR) in this series. Among the areas explored: side-chain SAR (aromatic-, heterocyclic-, and tricyclic-containing side chains) and modifications to the tetrahydropyridine ring. The benzhydrol ether-containing side chains afforded the most potent compounds with several exhibiting in vitro IC50 values for GABA uptake of <1 muM (including 5, Table 1; 37, 43, Table IV; and 44, Table V). Compound 44 was selected for extensive evaluation and subsequently progressed to Phase 1 clinical trials with severe adverse effects seen after single dose administration to humans.

  DOI：

  10.1021/jm00100a032
• 作为产物：
  描述：

  肉桂酸乙酯 在 palladium dihydroxide 氢气 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙醇 、 乙腈 为溶剂， 65.0 ℃ 、100.0 kPa 条件下， 生成 ethyl 3,4-diphenylbutanoate
  参考文献：
  名称：

  钯催化的苄基硝基键裂解：不对称合成的新机会。

  摘要：

  DOI：

  10.1002/anie.200604263

文献信息

• Rhodium Porphyrin Catalyzed Regioselective Transfer Hydrogenolysis of C–C σ-Bonds in Cyclopropanes with ^<i>i</i>PrOH
  作者：Chen Chen、Shiyu Feng、Kin Shing Chan

  DOI：10.1021/acs.organomet.9b00290

  日期：2019.6.24

  porphyrin catalyzed regioselective transfer hydrogenolysis of both activated and unactivated cyclopropanes employing iPrOH as the hydrogen source was discovered. The reaction mechanism for the C–C σ-bond activation of cyclopropanes was identified through an initial radical substitution with rhodium(II) metalloporphyrin radical to give a rhodium porphyrin alkyl, followed by hydrogenolysis with iPrOH to give

  发现了一种新的铑卟啉以i PrOH为氢源催化活化和未活化环丙烷的区域选择性转移氢解反应。通过用金属卟啉铑（II）进行初始自由基取代以生成卟啉烷基铑，然后用i PrOH氢解以生成相应的无环烷烃并再生铑，从而确定了环丙烷C–Cσ键活化的反应机理。（二）金属卟啉自由基。
• Silyl Phosphites. XVIII. Versatile Utility of α-(Trimethylsilyloxy)alkylphosphonates as Key Intermediates for Transformation of Aldehydes into Several Carbonyl Derivatives
  作者：Mitsuo Sekine、Masashi Nakajima、Akiko Kume、Akio Hashizume、Tsujiaki Hata

  DOI：10.1246/bcsj.55.224

  日期：1982.1

  trimethylsilyl phosphite (DTMSP) with aldehydes were converted, by treatment with lithium diisopropylamide (LDA) followed by the successive alkylation and alkaline hydrolysis, to carbonyl derivatives involving aldehydes, unsymmetrical ketones, β,γ-unsaturated ketones, and carboxylic acids. β-Substituted carboxylic esters and γ-substituted lactones were prepared by use of the carbonyl addition compounds of DTMSP

  通过用二异丙基氨基锂 (LDA) 处理，然后连续烷基化和碱水解，将二乙基三甲基甲硅烷基亚磷酸酯 (DTMSP) 与醛的羰基加成化合物转化为涉及醛、不对称酮、β,γ-不饱和酮和羧酸的羰基衍生物酸。利用DTMSP的羰基加成化合物与α,β-不饱和醛制备β-取代羧酸酯和γ-取代内酯。
• Facile synthesis of β-alkyl-substituted esters from α,β-unsaturated aldehydes
  作者：Tsujiaki Hata、Masashi Nakajima、Mitsuo Sekine

  DOI：10.1016/s0040-4039(01)86259-6

  日期：1979.1

  β-Alkyl-substituted carboxylates were synthesized in good yields from α,β-unsaturated aldehydes by using the 1:1 carbonyl adducts with diethyl bis (trimethylsilyl) phosphite.

  通过与亚乙基双（三甲基甲硅烷基）亚磷酸酯的1：1羰基加成反应，由α，β-不饱和醛以高收率合成β-烷基取代的羧酸盐。
• Benzotriazole- and 1,2,4-Triazole-Stabilized Allylic Anions:  Applications in Syntheses of Functionalized α,β-Unsaturated Ketones, γ-Lactones, γ-Lactams, and β-Substituted Esters
  作者：Alan R. Katritzky、Daming Feng、Hengyuan Lang

  DOI：10.1021/jo961396t

  日期：1997.2.1

  Deprotonated 1-(benzotriazol-1-yl)-1-ethoxy-2-hexene (7) reacted with alkyl halides, aldehydes, ketones, imines, and alpha-beta-unsaturated esters to give exclusively the alpha-alkylated products 8a-c, 10a,b, 12, 14, 16, and 18a,b, respectively. Without isolation, these products were hydrolyzed under mild conditions to generate the corresponding simple or functionalized alpha,beta-unsaturated ketones 9a-c, 11a,b, 13, 15, 17, and 19a,b. Similar reactions with the phenyl-substituted analog 3-(benzotriazol-1-yl)-3-ethoxy-1-phenyl-1-propene (21) also gave the analogous alpha-products, but they were accompanied by small amount of the gamma-products in most cases. By contrast, deprotonation of the corresponding triazole derivative 29 with butyllithium followed by reactions with alkyl halides, aldehydes, ketones, or imines yielded exclusively gamma-alkylated adducts 32, 34, 36, 38, 40, and 42. Intermediates 32, 34, 36, 38, 40, and 42 were readily converted into beta-substituted esters 33a-c, gamma-lactones 35a,b, 39, 41, and 43, and gamma-lactams 37a-c on hydrolysis.
• HATA TSUJIAKI; NAKAJIMA MASASHI; SEKINE MITSUO, TETRAHEDRON LETT., 1979, NO 22, 2047-2050
  作者：HATA TSUJIAKI、 NAKAJIMA MASASHI、 SEKINE MITSUO

  DOI：——

  日期：——