(5R)-γ-valerolactone γ-carboxylic acid | 21461-86-9

• 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: (5R)-γ-valerolactone γ-carboxylic acid
• 英文别名: (R)-tetrahydro-5-oxo-2-methyl-2-furancarboxylic acid；(R)-2-methyl-5-oxotetrahydrofuran-2-carboxylic acid；2-methyl-5-oxotetrahydrofuran-2-carboxylic acid；(R)-2-methyl-5-oxo-tetrahydro-furan-2-carboxylic acid；(R)-2-Methyl-5-oxo-tetrahydro-furan-2-carbonsaeure；(R)-2-Methyl-5-oxo-tetrahydrofuran-2-carbonsaeure；(2R)-2-methyl-5-oxooxolane-2-carboxylic acid
• CAS: 21461-86-9
• 化学式: C₆H₈O₄
• 分子量: 144.127
• InChiKey: WFCVTCIMBXTXFJ-ZCFIWIBFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2932190090

反应信息

• 作为反应物：
  描述：

  (5R)-γ-valerolactone γ-carboxylic acid 在 lithium aluminium tetrahydride 作用下， 生成 (R)-(+)-2-Methyl-1,2,5-pentantriol
  参考文献：
  名称：

  额叶蛋白光学活性形式的合成：树枝状树皮甲虫的信息素

  摘要：

  （- [R ）- （+） - Frontalin（1）和与其对映体（1 '）是从（合成- [R（+） - - ）2-羟基-2-甲基戊烷-1,5-二酸5→2内酯（2）及其对映体（2 '）。这建立了额叶蛋白两个对映异构体的绝对构型，并为研究信息素活性与手性之间的关系提供了关键材料。

  DOI：

  10.1016/0040-4020(75)87067-0
• 作为产物：
  描述：

  甲基环戊烯醇酮 在 titanium(IV) isopropylate 、 L-(+)-酒石酸二乙酯 、 叔丁基过氧化氢 作用下， 以 二氯甲烷 、 癸烷 为溶剂， 反应 48.5h， 以75%的产率得到(5R)-γ-valerolactone γ-carboxylic acid
  参考文献：
  名称：

  Asymmetric Synthesis of Tertiary 2-Substituted 5-Oxotetrahydrofuran-2-carboxylic Acids

  摘要：

  3-Substituted 1,2-cyclopentanediones 1 were transformed to 2-substituted 5-oxotetrahydrofuran-2-carboxylic acids 2 using a catalytic process with 0.2-0.3 equivalent of Ti(OiPr)(4)/tartaric ester/tBuO0H complex in up to 72% isolated yield and up to 94% ee. Different functional groups in the 3-alkyl substituent of 1 like, hydroxy, ether, Boc-amino and ester groups are tolerated. Boc-aminomethyl substitu.ents lead to beta-amino acid analogues and Boc-aminoethyl substituent to gamma-amino acid analogues as well as spiro-lactonelactams. A direct, two-step procedure for homocitric acid synthesis is described.

  DOI：

  10.3987/com-13-s(s)28

文献信息

• Asymmetric oxidation of 3-alkyl-1,2-cyclopentanediones. Part 2: Oxidative ring cleavage of 3-alkyl-1,2-cyclopentanediones: synthesis of 2-alkyl-γ-lactone acids
  作者：Anne Paju、Tõnis Kanger、Tõnis Pehk、Rasmus Lindmaa、Aleksander-Mati Müürisepp、Margus Lopp

  DOI：10.1016/s0957-4166(03)00309-4

  日期：2003.6

  Ti(OiPr)4/diethyl tartrate/tBuOOH system oxidizes 3-alkyl-1,2-cyclopentanediones resulting in hydroxylated ring cleavage products 2-alkyl-γ-lactone acids, in high enantioselectivity (∼95% ee) and satisfactory isolated yields (up to 55%).

  Ti（O i Pr）4 /酒石酸二乙酯/ t BuOOH体系氧化3-烷基-1,2-环戊二酮，生成羟化的环裂解产物2-烷基-γ-内酯酸，对映体选择性高（〜95％ee），令人满意单产（最高55％）。
• Asymmetric radical additions using chiral 1,3-dioxolane-4-ones
  作者：Georg Kneer、Jochen Mattay

  DOI：10.1016/s0040-4039(00)74714-9

  日期：1992.12

  selectivities are observed in additions of alkyl radicals to the chiral (c,d) olefin (2S)-2-tert-butyl-5-ethoxycarbonylmethylene-1,3-dioxolane-4-one1. The following hydrogen abstraction from tributylstannane proceeds with excellent asymmetric stereocontrol, leading to two of four possible diastereoisomers with high diastereomeric excesses. Additions of chiral radicals obtained from (2R,5R)-5-alkyl-5-bromo-1

  在手性（c，d）烯烃（2 S）-2-叔丁基-5-乙氧基羰基亚甲基-1,3-二氧戊环-4-酮1上添加烷基后，观察到适度的面部选择性。随后从三丁基锡烷提取氢的过程具有出色的不对称立体控制，从而导致四种可能的非对映异构体中的两个具有高非对映异构体过量度。由（2 R，5 R）-5-烷基-5-溴-1,3-二氧戊环-4-酮获得的手性基团向丙烯酸乙酯的加成表现出高度的不对称1,3-诱导作用。
• Highly<i>Z</i>-Selective Asymmetric 1,4-Addition Reaction of 5<i>H</i>-Oxazol-4-ones with Alkynyl Carbonyl Compounds Catalyzed by Chiral Guanidines
  作者：Tomonori Misaki、Kei Kawano、Takashi Sugimura

  DOI：10.1021/ja200283n

  日期：2011.4.20

  An asymmetric I,4-addition reaction of 5H-oxazol-4-ones with alkynyl carbonyl compounds was developed, and, for the first time, high enantiomeric and geometric control was achieved to afford the thermodynamically unstable Z-isomer predominantly using chiral guanidine catalysts bearing a hydroxy group at the appropriate position. The method provides synthetically useful gamma-butenolide ester bearing a chiral quaternary stereogenic center.
• Stereoselective Radical Additions using chiral 1,3-dioxolanones derived from lactic and malic acid
  作者：Georg Kneer、Jochen Mattay、Andreas Heidbreder、Gerhard Raabe、Bernt Krebs、Mechtild L�ge

  DOI：10.1002/prac.19953370126

  日期：——

  The hydrogen abstraction of radical intermediates yielded by radical addition to the methylene compound 6, shows excellent facial selectivity. Conformational analyses of the radical intermediates were carried out by quantum chemical calculations and explain these results. The chiral radicals 7 and 8, yielded from the chiral bromides 3 and 4, lead with ethyl acrylate to the adducts 28 and 29 with more 96 % de. The adduct 28 was converted to the optically active gamma-valerolactone 30. The structures of the bromides 3, 4 and 31 as well as the radical adducts 19a, 24 and 25 have been verified by X-ray diffraction analysis.
• Synthesis and structure proof of a vitamin D3 metabolite, 25(s),26-dihydroxycholecalciferol
  作者：John J. Partridge、Shian Jan Shiuey、Naresh K. Chadha、Enrico G. Baggiolini、John F. Blount、Milan R. Uskokovic

  DOI：10.1021/ja00395a061

  日期：1981.3