(+)-β-methyl-α-methylene-γ-butyrolactone | 62322-50-3

• 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-methyl-α-methylene-γ-butyrolactone
• 英文别名: 3-methylene-4(R)-methyldihydro-2-furanone；2(3H)-Furanone, dihydro-4-methyl-3-methylene-, (R)-；(4R)-4-methyl-3-methylideneoxolan-2-one
• CAS: 62322-50-3
• 化学式: C₆H₈O₂
• 分子量: 112.128
• InChiKey: ZFHFDZCWLKLJPP-BYPYZUCNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 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-methyl-α-methylene-γ-butyrolactone 以 甲苯 为溶剂， 反应 5.0h， 生成 xyloketal D
  参考文献：
  名称：

  Total synthesis of (+)-xyloketal D, a secondary metabolite from the mangrove fungus Xylaria sp.

  摘要：

  将以下文本翻译成中文： (+)-Xyloketal D was prepared in a one-pot multistep domino reaction by heating optically active 5-hydroxy-4-methyl-3-methylenepentan-2-one (R) in toluene with 2,4-dihydroxyacetophenone. The absolute configuration of the natural product was confirmed by preparation of the starting enone from a lactone of established absolute configuration. (C) 2003 Elsevier Ltd. All rights reserved. 翻译如下： （+）-Xyloketal D 通过在多步多米诺反应中将具有光学活性的 5-羟基-4-甲基-3-甲烯 Pentan-2-one（R）与 2,4-二羟基乙酰苯酮一起在甲苯中加热制得。天然产物的绝对构型通过从具有已知绝对构型的内酯制备起始烯酮得到确认。© 2003 Elsevier Ltd. 保留所有权利。

  DOI：

  10.1016/j.tetlet.2003.10.189
• 作为产物：
  描述：

  (E)-4-hydroxy-3-methylbut-2-enoic acid 在 chiral ruthenium catalyst 、 氢气 、 sodium hydride 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 甲酸乙酯 作用下， 生成 (+)-β-methyl-α-methylene-γ-butyrolactone
  参考文献：
  名称：

  Total synthesis of (+)-xyloketal D, a secondary metabolite from the mangrove fungus Xylaria sp.

  摘要：

  将以下文本翻译成中文： (+)-Xyloketal D was prepared in a one-pot multistep domino reaction by heating optically active 5-hydroxy-4-methyl-3-methylenepentan-2-one (R) in toluene with 2,4-dihydroxyacetophenone. The absolute configuration of the natural product was confirmed by preparation of the starting enone from a lactone of established absolute configuration. (C) 2003 Elsevier Ltd. All rights reserved. 翻译如下： （+）-Xyloketal D 通过在多步多米诺反应中将具有光学活性的 5-羟基-4-甲基-3-甲烯 Pentan-2-one（R）与 2,4-二羟基乙酰苯酮一起在甲苯中加热制得。天然产物的绝对构型通过从具有已知绝对构型的内酯制备起始烯酮得到确认。© 2003 Elsevier Ltd. 保留所有权利。

  DOI：

  10.1016/j.tetlet.2003.10.189

文献信息

• 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。
• POLYMER COMPOSITION, PLASTIC OPTICAL FIBER, PLASTIC OPTICAL FIBER CABLE AND METHOD FOR PRODUCING PLASTIC OPTICAL FIBER
  申请人：MITSUBISHI RAYON CO., LTD.

  公开号：EP1834968A1

  公开（公告）日：2007-09-19

  There is provided a polymer composition comprising 5 to 100% by mass of a unit (A) of a lactone compound represented by a general formula (1) and 0 to-95% by mass of a unit (B) of (meth)acrylate as constitutional units, wherein the unit (A) of a lactone compound comprises a unit of an (S) isomer represented by a general formula (2) and a unit of an (R) isomer represented by a general formula (3) at a mass ratio of from 70/30 to 30/70; and wherein the polymer composition has a total light scattering loss of not more than 100 dB/km. The polymer composition is excellent in heat resistance and transparency.

  本发明提供了一种聚合物组合物，该聚合物组合物包含 5%至 100%（以质量计）的通式（1）所代表的内酯化合物单元（A）和 0%至 95%（以质量计）的（甲基）丙烯酸酯单元（B）作为组成单元，其中内酯化合物单元（A）包含通式（2）所代表的（S）异构体单元和通式（3）所代表的（R）异构体单元，两者的质量比为 70/30 至 30/70；其中聚合物组合物的总光散射损耗不超过 100 dB/km。该聚合物组合物具有优异的耐热性和透明度。
• Stereospecificity in allergic contact dermatitis to simple substituted methylene lactones derivatives
  作者：Henri Mattes、Kaoru Hamada、Claude Benezra

  DOI：10.1021/jm00394a003

  日期：1987.11

  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.
• 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：——