(Z)-α-hexylidene-γ-butyrolactone | 67404-96-0

• 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: (Z)-α-hexylidene-γ-butyrolactone
• 英文别名: (3Z)-3-hexylideneoxolan-2-one
• CAS: 67404-96-0
• 化学式: C₁₀H₁₆O₂
• 分子量: 168.236
• InChiKey: SSPHFANWMRSHAL-TWGQIWQCSA-N

物化性质

• 沸点：
  115-117 °C(Press: 1.1 Torr)
• 密度：
  1.054±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 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：

  (Z)-α-hexylidene-γ-butyrolactone 在 calcium oxide 作用下， 以 二氯甲烷 为溶剂， 反应 36.0h， 生成 Acetic acid (S)-1-((S)-3-ethoxycarbonylamino-2-oxo-tetrahydro-furan-3-yl)-hexyl ester
  参考文献：
  名称：

  Synthesis of α-amino γ-butyrolactone derivatives by aziridination of α-ylidene γ-butyrolactones

  摘要：

  The reactions of exocyclic alpha,beta-unsaturated gamma-lactones with NsONHCO(2)Et and CaO produce N-(ethoxycarbonyl) spiroaziridino gamma-lactones. By reaction with acetic acid these products give ring opening reaction and acetylated N-protected alpha-amino gamma-butyrolactones are obtained. The ring opening reaction is quantitative and highly regioselective. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01166-3
• 作为产物：
  描述：

  1-(2-oxooxolan-3-yl)hexyl methanesulfonate 生成 (Z)-α-hexylidene-γ-butyrolactone
  参考文献：
  名称：

  ITOKAWA, HIDEJI;OSHIMA, TOSHIYUKI;MATSUMOTO, HAJIME;MIHASHI, SUSUMU, J. PHARM. SOC. JAP., 1984, 104, N 8, 839-847

  摘要：

  DOI：

文献信息

• Stereoselective Synthesis of (<i>E</i>)- or (<i>Z</i>)-α-Alkylidene-γ-butyrolactone from γ-Butyrolactone and Bis[ethoxy(thiocarbonyl)] Disulfide and Mechanistic Studies of the Effect of Metal Complexes on the Stereoselection
  作者：Syuichi Matsui

  DOI：10.1246/bcsj.60.1853

  日期：1987.5

  with an aldehyde to afford exclusively (E)-α-alkylidene-γ-butyrolactone. Interestingly, when the reaction was quenched below −20 °C or when it was carried out in the presence of metal complex such as zinc chloride, copper(I) iodide, or tributyltin chloride, (Z)-α-alkylidene-γ-butyrolactone was obtained as the major product. The stereoselectivity of this reaction was sensitive to the reaction temperature

  在 2.2 当量二异丙基氨基锂 (LDA) 存在下，用双 [乙氧基（硫代羰基）] 二硫化物处理 γ-丁内酯，生成 O-乙基 S-（四氢-2-氧代-3-呋喃基）二硫代碳酸酯的烯醇锂，其反应用醛生成仅 (E)-α-亚烷基-γ-丁内酯。有趣的是，当反应在 -20 °C 以下猝灭或在金属络合物（如氯化锌、碘化铜（I）或氯化三丁基锡、（Z）-α-亚烷基-γ-丁内酯）存在下进行时作为主要产品获得。该反应的立体选择性对反应温度和所用金属阳离子敏感。
• 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。
• Synthesis of α-Alkylidene-β-Ethoxycarbonyl Cyclopentanones and -γ-Butyrolactones
  作者：Beji、Besbes、Amri

  DOI：10.1080/00397910008086954

  日期：2000.11

  Synthesis of (E,Z)-alpha-Alkylidene-beta-ethoxycarbonyl cyclopentanones 5 and(E,Z)-alpha-alkylidene-gamma-butyrolactones 7 by condensing phosphonates 3 or 6 with a variety of aldehydes in the presence of aqueous potassium carbonate (6-10M) as base is reported.
• MATSUI SYUICHI, BULL. CHEM. SOC. JAP., 60,(1987) N 5, 1853-1865
  作者：MATSUI SYUICHI

  DOI：——

  日期：——
• TANAKA K.; UNEME H.; YAMAGISHI N.; ONO N.; KAJI A., CHEM. LETT., 1978, NO 6, 653-656
  作者：TANAKA K.、 UNEME H.、 YAMAGISHI N.、 ONO N.、 KAJI A.

  DOI：——

  日期：——