(E)-α-(α-methylbenzylidene)-γ-butyrolactone | 67404-97-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-α-(α-methylbenzylidene)-γ-butyrolactone
• 英文别名: (E)-α-(1-phenylethylidene)-γ-butyrolactone；(3E)-3-(1-phenylethylidene)dihydrofuran-2(3H)-one；(E)-3-(1-phenylethylidene)dihydro-2(3H)-furanone；(3E)-3-(1-phenylethylidene)oxolan-2-one
• CAS: 67404-97-1
• 化学式: C₁₂H₁₂O₂
• 分子量: 188.226
• InChiKey: CDSOUUVJFYPOFR-PKNBQFBNSA-N

物化性质

• 熔点：
  76-77 °C(Solv: ligroine (8032-32-4); ethyl acetate (141-78-6))
• 沸点：
  123 °C(Press: 0.5 Torr)
• 密度：
  1.148±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  (E)-α-(α-methylbenzylidene)-γ-butyrolactone 在 palladium on activated charcoal sodium periodate 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 水 、 溶剂黄146 、 甲苯 为溶剂， 反应 19.0h， 生成 8-methyl-3,3a,8,8a-tetrahydro-1H-indeno<1,2-c>furan-1-one
  参考文献：
  名称：

  A Breakthrough for the Photochemical Arylation in the 3-(Phenylmethyl)-2(5H)-furanone system Leading to the Tetrahydroindenofuranone System

  摘要：

  The photochemistry of the 'central methane'-substituted 3-benzyl-2(5H)-furanone system (1) is described. Despite its di-pi-methane structure, photochemical arylation was found to predominate in place of the di-pi-methane rearrangement, and gave substituted tetrahydroindenofuranones (2) in good yields.

  DOI：

  10.3987/com-92-6034
• 作为产物：
  描述：

  生成 (E)-α-(α-methylbenzylidene)-γ-butyrolactone
  参考文献：
  名称：

  A Breakthrough for the Photochemical Arylation in the 3-(Phenylmethyl)-2(5H)-furanone system Leading to the Tetrahydroindenofuranone System

  摘要：

  The photochemistry of the 'central methane'-substituted 3-benzyl-2(5H)-furanone system (1) is described. Despite its di-pi-methane structure, photochemical arylation was found to predominate in place of the di-pi-methane rearrangement, and gave substituted tetrahydroindenofuranones (2) in good yields.

  DOI：

  10.3987/com-92-6034

文献信息

• Tandem Blaise/retro-Blaise Reaction for the Nitrile-Mediated Regioselective Intermolecular Addition of Unstabilized Zinc Ester Enolates (Reformatsky Reagents) to 1-Alkynes and 1,3-Enynes
  作者：Ju Hyun Kim、Yu Sung Chun、Sang-gi Lee

  DOI：10.1021/jo402015n

  日期：2013.11.15

  of a nitrile as a mediator to achieve the regioselective intermolecular addition of unstabilized zinc ester enolates (Reformatsky reagents) to 1-alkynes and 1,3-enynes. This reaction is made possible by a reversible addition of enolates to a nitrile (Blaise reaction), generating a zinc aza-enolate that, unlike zinc ester enolates, can add intermolecularly to 1-alkynes and 1,3-enynes. Subsequent removal

  我们报道了一种新型的腈作为介体的新用途，以实现对不稳定的区域选择性分子间加成的不稳定的锌酯烯酸酯（Reformatsky试剂）到1-炔烃和1,3-烯炔烃。通过将烯酸酯可逆地添加到腈中（布莱斯反应），可以生成该反应，生成氮杂-烯醇锌，与酯烯酸酯锌不同，可以将分子间添加到1-炔烃和1,3-烯炔中。随后通过逆Blaise反应除去腈可生成目标加成产物。该方法与Diels-Alder反应和随后的氧化芳构化相结合，可从Reformatsky试剂串联一锅从头开始构建α-芳基链烷酸酯。
• New Methods for Stereoselective Synthesis of α-Alkylidene-γ-butyrolactones Using Monoanion of<i>O</i>-Ethyl<i>S</i>-(Tetrahydro-2-oxo-3-furanyl) Thiocarbonate and Dianion of α-Mercapto-γ-butyrolactone
  作者：Kazuhiko Tanaka、Hideki Uneme、Nobuyuki Yamagishi、Rikuhei Tanikaga、Aritsune Kaji

  DOI：10.1246/bcsj.53.2910

  日期：1980.10

  The lithium enolates of O-ethyl S-(tetrahydro-2-oxo-3-furanyl) dithiocarbonate and thiocarbonate were found to be efficient reagents for the stereoselective synthesis of α-alkylidene-γ-butyrolactones from carbonyl compounds. The dianion of α-mercapto-γ-butyrolactone was successfully generated by treatment of α-mercapto-γ-butyrolactone with 2.2 equivalents of lithium diisopropylamide in the presence

  发现 O-乙基 S-(四氢-2-氧代-3-呋喃基)二硫代碳酸酯和硫代碳酸酯的锂烯醇化物是从羰基化合物立体选择性合成 α-亚烷基-γ-丁内酯的有效试剂。α-巯基-γ-丁内酯的二价阴离子是在-78°C、N,N,N',N'-四甲基乙二胺存在下，用2.2当量的二异丙基氨基锂处理α-巯基-γ-丁内酯而成功生成的。四氢呋喃。由此形成的二价阴离子已被用于从羰基化合物有效和立体选择性地合成 α-亚烷基-γ-丁内酯。
• De, Dibyendu; Seth, M.; Bhaduri, A. P., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1989, vol. 28, # 1-11, p. 503 - 506
  作者：De, Dibyendu、Seth, M.、Bhaduri, A. P.

  DOI：——

  日期：——
• Highly Selective Nickel-Catalyzed Methyl-Carboxylation of Homopropargylic Alcohols for α-Alkylidene-γ-butyrolactones
  作者：Suhua Li、Shengming Ma

  DOI：10.1021/ol202520x

  日期：2011.11.18

  A first practical Ni(0)-catalyzed highly stereoselective methyl-carboxylation of homopropargylic alcohols with ZnMe2 and CO2 for the efficient synthesis of alpha-alkylidene-gamma-butyrolactones is described. The reaction may be applied to other alkynols.
• The chemistry of .alpha.-silyl carbonyl compounds. 10. A two-step preparation of .alpha.-alkylidene .gamma.-lactones from .gamma.-lactones: a synthesis of (.+-.)-ancepsenolide
  作者：Gerald L. Larson、Rosa M. Betancourt de Perez

  DOI：10.1021/jo00225a052

  日期：1985.12