(R)-4-butyl-1-(4-methoxyphenyl)-2-pyrrolidinone | 174618-40-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (R)-4-butyl-1-(4-methoxyphenyl)-2-pyrrolidinone
• 英文别名: (4R)-4-butyl-1-(4-methoxyphenyl)pyrrolidin-2-one
• CAS: 174618-40-7
• 化学式: C₁₅H₂₁NO₂
• 分子量: 247.337
• InChiKey: NVSLPXULQXNFPK-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-4-butyl-1-(4-methoxyphenyl)-2-pyrrolidinone 在 sodium hydroxide 、 lithium aluminium tetrahydride 、 ammonium cerium(IV) nitrate 作用下， 以 水 、 乙腈 为溶剂， 反应 19.5h， 生成 (R)-3-Butyl-pyrrolidine-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Steric and Electronic Influences on the Diastereoselectivity of the Rh₂(OAc)₄-Catalyzed C−H Insertion in Chiral Ester Diazoanilides:  Synthesis of Chiral, Nonracemic 4-Substituted 2-Pyrrolidinones

  摘要：

  A series of N-substituted N-(4-methoxyphenyl)-alpha-(alkoxycarbonyl)-alpha-diazoacetanilides, 10 and ent-10, wherein the alkoxy unit is a chiral auxiliary group [(-)-7 or (+)-8)], was prepared. The Rh-2(OAc)(4)-catalyzed intramolecular C-H insertion reaction of 10 and ent-10, under optimized reaction conditions, was investigated as a route for the preparation of chiral, nonracemic 4-substituted 2-pyrrolidinones. The cyclization reaction led only to 2-pyrrolidinone and 2-azetidinone products; the former products were obtained as major and, in a few cases, as exclusive products. The type and nature of the N-substituent in 10 or ent-10 was found to govern the diastereoselectivity of the reaction. With N-alkyl groups, steric effects play an important role in determining the diastereoselectivity of the reaction. However, with N-arylethyl substituents, electronic effects transmitted by the aryl substituents influenced the diastereoselectivity of the C-H insertion reaction. Specifically, electron-donating substituents were found to markedly attenuate the diastereoselectivity of the reaction. The diastereoselectivity of the reaction ranged from moderate to high (37-98%). A transition-state model to explain the observed diastereoselectivity is provided. The synthetic utility of the method is demonstrated by the stereoselective synthesis of the medicinally important, unnatural amino acid trans-4-cyclohexyl-L-proline 23.

  DOI：

  10.1021/jo971540q
• 作为产物：
  描述：

  (S)-N-(4-methoxyphenyl)-3,4-dihydroxy-3,4-O-isopropylidenebutanamide 在 吡啶 、 盐酸 、 甲醇 、 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 copper(I) bromide dimethylsulfide complex 、 rhodium(II) pivalate 、 偶氮二异丁腈 、 potassium tert-butylate 、 三正丁基氢锡 、 lithium 、 potassium hydride 、 二甲基亚砜 、 N,N-二异丙基乙胺 、 甲烷磺酰基叠氮化物 、 N,N'-二环己基碳二亚胺 、 sodium chloride 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 乙醇 、 二氯甲烷 、 氯仿 、 甲苯 、 乙腈 、 苯 为溶剂， 反应 186.92h， 生成 (R)-4-butyl-1-(4-methoxyphenyl)-2-pyrrolidinone
  参考文献：
  名称：

  Rh(II)催化的N-[4-{(S)-1,2-二羟基丁基}]-α-重氮苯胺衍生物的CH插入反应的研究：位点选择性

  摘要：

  DOI：

  10.3987/com-99-8805

文献信息

• Catalytic Enantioselective Conjugate Reduction of Lactones and Lactams
  作者：Gregory Hughes、Masanari Kimura、Stephen L. Buchwald

  DOI：10.1021/ja0351692

  日期：2003.9.1

  A dramatic acceleration of the enantioselective copper-catalyzed conjugate reduction of alpha,beta-unsaturated lactones, lactams, and esters is reported upon addition of alcohol additives. Good to excellent yields and enantioselectivities were realized using a catalyst generated in situ from CuCl(2).H(2)O, t-BuONa, p-tol-BINAP, and PMHS, and this methodology was applied to the synthesis of (-)-Paroxetine

  据报道，在添加醇添加剂后，α、β-不饱和内酯、内酰胺和酯的对映选择性铜催化共轭还原显着加速。使用由 CuCl(2).H(2)O、t-BuONa、p-tol-BINAP 和 PMHS 原位生成的催化剂实现了良好到优异的产率和对映选择性，并且该方法用于合成 (- )-帕罗西汀。