(S)-β-(2-propyl)-γ-butyrolactone | 80410-19-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (S)-β-(2-propyl)-γ-butyrolactone
• 英文别名: R-β-isopropyl-γ-butyrolactone；(+)-(R)-3-isopropylbutyro-1,4-lactone；(R)-4-isopropyldihydrofuran-2(3H)-one；(R)-(+)-3-(2'-propyl)butyrolactone；4-isopropyldihydrofuran-2-one；(4R)-4-propan-2-yloxolan-2-one
• CAS: 80410-19-1
• 化学式: C₇H₁₂O₂
• 分子量: 128.171
• InChiKey: KSHNENOHFJQWJE-LURJTMIESA-N

物化性质

• 沸点：
  208.1±8.0 °C(Predicted)
• 密度：
  0.998±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (4R,5S)-3-<1-oxo-3-(1,3-dithian-2-ylidene)-2-(2-propyl)propyl>-4-methyl-5-phenyl-2-oxazolidinone 在 lithium aluminium tetrahydride 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.5h， 生成 (S)-β-(2-propyl)-γ-butyrolactone
  参考文献：
  名称：

  Enantioselective preparation of .beta.-alkyl-.gamma.-butyrolactones from functionalized ketene dithioacetals

  摘要：

  An efficient and general enantioselective synthesis of beta-alkyl-gamma-butyrolactones has been developed. The key step of this procedure is an oxazolidinone-directed alkylation of a lithiated ketene dithioacetal that proceeds with excellent regiochemical control and high diastereofacial selectivity. Reductive removal of the chiral auxiliary followed by acid-induced cyclization of the resultant hydroxy ketene dithioacetal gives the enantiomerically pure beta-alkyl-gamma-butyrolactone.

  DOI：

  10.1021/jo00062a013

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。
• Asymmetric synthesis. Part 6. Copper salt promoted grignard reagent additions to ethyl 2,3-dideoxy-4,5:6,7-di-O-isopropylidene-D-arabino-trans-hept-2-enonate and subsequent formation of optically active 2-alkyl (or aryl) butane-1,4-dioic acids and butyro-1,4-lactones
  作者：Ian W. Lawston、Thomas D. Inch

  DOI：10.1039/p19830002629

  日期：——

  The copper-salt promoted 1,4-additions of aryl and t-butyl Grignard reagents to ethyl 2,3-dideoxy-4,5:6,7-di-O-isopropylidene-D-arabino-trans-hept-2-enonate are highly stereoselective yielding products with the D-manno-configuration. In contrast isopropyl and ethyl Grinard reagents give products preponderantly with the D-gluco-configuration. Cyclohexylmagnesium bromide does not react stereoselectively

  铜盐促进芳基和叔丁基格氏试剂的1,4-增补乙基-2,3-二脱氧-4,5-：6,7-二- ö异亚丙基d -阿拉伯-反式-庚-2- enonate是高度立体收益产品与d -甘露-构型。相比之下异丙基和乙基格氏试剂，得到的产品主要发生与d -葡萄糖-构型。环己基溴化不立体选择性反应，但给出了一个55：在45混合物d -葡糖-和d -甘露-异构体。碳水化合物分子的受控降解提供了2-芳基（烷基）丁烷-1,4-二酸和3-芳基（烷基）-丁酰基-1,4-内酯。这些产物的对映体纯度是通过参考已知产物或通过使用光学活性nMR位移试剂来确定的。
• Regioselective Hydrogenation of Unsymmetrically Substituted Cyclic Anhydrides Catalyzed by Ruthenium Complexes with Phosphine Ligands
  作者：Takao Ikariya、Kohtaro Osakada、Youichi Ishii、Shoichi Osawa、Masahiko Saburi、Sadao Yoshikawa

  DOI：10.1246/bcsj.57.897

  日期：1984.3

  Regioselective hydrogenation of unsymmetrically substituted cyclic anhydrides catalyzed by ruthenium complexes with mono-, di-, or triphosphine ligands produced the corresponding two isomeric lactones, where the regioselectivity was influenced by the bulkiness of the substituent(s) on the anhydrides and of the phosphine ligands of catalyst.

  由钌配合物与单、二或三膦配体催化的不对称取代环酐的区域选择性氢化产生相应的两种异构内酯，其中区域选择性受酸酐上取代基和膦配体的体积影响的催化剂。
• ASYMMETRIC SYNTHESIS OF β-SUBSTITUTED γ-BUTYROLACTONES
  作者：Teruaki Mukaiyama、Katsumi Fujimoto、Takuji Hirose、Takeshi Takeda

  DOI：10.1246/cl.1980.635

  日期：1980.6.5

  Highly optically pure β-substituted γ-butyrolactones (V) were obtained in good yields by the reaction of (E)-(2R,3S)-6-alkylidene-3,4-dimethyl-2-phenylperhydro-1,4-oxazepine-5,7-dione (I) with phenylthiomethyllithium, followed by i) treatment with trimethyloxonium tetrafluoroborate and ii) acid hydrolysis.

  通过 (E)-(2R,3S)-6-亚烷基-3,4-二甲基-2-苯基全氢-1,4-oxazep​​ine 的反应，以良好的收率获得了高光学纯度的 β-取代 γ-丁内酯 (V) -5,7-二酮 (I) 与苯基硫代甲基锂，然后 i) 用三甲基氧鎓四氟硼酸盐处理和 ii) 酸水解。
• THERAPEUTIC COMPOUNDS
  申请人：Gilead Sciences, Inc.

  公开号：US20160083368A1

  公开（公告）日：2016-03-24

  Compounds of formula I: or salts thereof are disclosed. Also disclosed are pharmaceutical compositions comprising a compound of formula I, processes for preparing compounds of formula I, intermediates useful for preparing compounds of formula I and therapeutic methods for treating a Retroviridae viral infection including an infection caused by the HIV virus.

  本发明揭示了化学式I的化合物或其盐。本发明还揭示了包括化合物I的药物组合物，制备化合物I的方法，用于制备化合物I的中间体以及治疗Retroviridae病毒感染，包括HIV病毒感染的治疗方法。