(+)-β,γ-dimethyl-α-methylene-γ-butyrolactone | 110171-20-5

• 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: (+)-β,γ-dimethyl-α-methylene-γ-butyrolactone
• 英文别名: 3-methylene-4(S),5(R)-dimethyldihydro-2-furanone；(4S,5R)-4,5-dimethyl-3-methylideneoxolan-2-one
• CAS: 110171-20-5
• 化学式: C₇H₁₀O₂
• 分子量: 126.155
• InChiKey: GWSGIIGWNQXFIJ-UJURSFKZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 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：

  (+)-β,γ-dimethyl-α-methylene-γ-butyrolactone 、 Boc-Cys-Ala-OMe 在 甲醇 、 sodium hydride 作用下， 反应 0.17h， 以97%的产率得到(+)-β,γ-methyl-α-methylene-γ-butyrolactone-Cys(Boc)-Ala(OMe) adduct
  参考文献：
  名称：

  BOC-CYS-ALA-OME的合成及其对α-亚甲基-γ-丁内酯的立体选择性加成

  摘要：

  已经研究了对映体纯（如200 MHz 1 H NMR研究所示）向α-亚甲基-γ-丁内酯中立体定向加成的二肽Boc-Cys-Ala-OMe 4。添加的立体选择性与在豚鼠诱发的过敏性接触性皮炎中观察到的对映选择性平行。

  DOI：

  10.1016/s0040-4020(01)81082-6
• 作为产物：
  描述：

  (4S,5R)-3-Dimethylaminomethyl-4,5-dimethyl-dihydro-furan-2-one 在 碘甲烷 作用下， 以 甲醇 为溶剂， 反应 20.0h， 生成 (+)-β,γ-dimethyl-α-methylene-γ-butyrolactone
  参考文献：
  名称：

  Stereospecificity in allergic contact dermatitis to simple substituted methylene lactones derivatives

  摘要：

  The enantiomers of beta,gamma-dimethyl- and beta-methyl-alpha-methylene-gamma-butyrolactones have been synthesized stereospecifically from glutamic acid and beta-hydroxy isobutyric acid, respectively. Guinea pigs have been sensitized (Freund complete adjuvant technique) and tested to them. Both enantiomers of beta-methyl lactone as well as (+)-beta,gamma-dimethyl lactone induced enantiospecific allergic contact dermatitis (ACD); in turn, (-)-beta,gamma-dimethyl lactone showed no specificity. An interpretation is proposed.

  DOI：

  10.1021/jm00394a003

文献信息

• A NEW SYNTHETIC ROUTE TO α-METHYLENE AND β-METHYLENE-γ-BUTYROLACTONES VIA HOMOLYTIC CARBOCYCLIZATION
  作者：Osamu Moriya、Makoto Okawara、Yoshio Ueno

  DOI：10.1246/cl.1984.1437

  日期：1984.8.5

  α-Methylene-γ-butyrolactones were prepared using butoxyallene via stereoselective homolytic carbocyclization of vinyl radicals, similarly, β-methylene analogues were also prepared.

  α-亚甲基-γ-丁内酯是使用丁氧基丙二烯通过乙烯基自由基的立体选择性均裂碳环化制备的，类似地，也制备了β-亚甲基类似物。
• Réactivité d'organozinciques allyliques β-fonctionnels γ-substitués. Préparation d'α-méthylène γ-butyrolactones β- et γ-substituées
  作者：François Lambert、Bernard Kirschleger、Jean Villiéras

  DOI：10.1016/0022-328x(91)83172-z

  日期：1991.3

  Stable organozinc compounds derived from alkyl 3-alkyl 2-(bromomethyl) propenoates reacted with ketones and aldehydes to give alpha-methylene gamma-butyrolactones in excellent yields. Different reaction parameters were studied and some transition states were proposed.
• TALAGA, PATRICE;SHAEFFER, MARCEL;MATTES, HENRI;BENEZRA, CLAUDE;STAMPF, JE+, TETRAHEDRON, 45,(1989) N6, C. 5029-5038
  作者：TALAGA, PATRICE、SHAEFFER, MARCEL、MATTES, HENRI、BENEZRA, CLAUDE、STAMPF, JE+

  DOI：——

  日期：——
• MATTES, HENRI;HAMADA, KAORU;BENEZRA, CLAUDE, J. MED. CHEM., 30,(1987) N 11, 1948-1951
  作者：MATTES, HENRI、HAMADA, KAORU、BENEZRA, CLAUDE

  DOI：——

  日期：——
• Synthesis of BOC-CYS-ALA-OME and its stereoselective addition to α-methylene-γ-butyrolactones
  作者：Patrice Talaga、Marcel Schaeffer、Henri Mattes、Claude Benezra、Jean-Luc Stampf

  DOI：10.1016/s0040-4020(01)81082-6

  日期：1989.1

  The stereoselective addition of enantiomerically pure (as shown by 200 MHz 1H NMR study) dipeptide Boc-Cys-Ala-OMe 4 to α-methylene-γ-butyrolactones has been studied. The stereoselectivity of the addition parallels the enantioselectivity observed in the allergic contact dermatitis induced in guinea pigs.

  已经研究了对映体纯（如200 MHz 1 H NMR研究所示）向α-亚甲基-γ-丁内酯中立体定向加成的二肽Boc-Cys-Ala-OMe 4。添加的立体选择性与在豚鼠诱发的过敏性接触性皮炎中观察到的对映选择性平行。