(S)-5-5(2-methylprop-1-en-1-yl)dihydrofuran-2(3H)-one | 100891-03-0

• 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: (S)-5-5(2-methylprop-1-en-1-yl)dihydrofuran-2(3H)-one
• 英文别名: (S)-dihydro-5-(2-methylprop-1-enyl)furan-2(3H)-one；(S)-5-(2-methylprop-1-en-1-yl)dihydrofuran-2(3H)-one；(5S)-5-(2-methylprop-1-enyl)oxolan-2-one
• CAS: 100891-03-0
• 化学式: C₈H₁₂O₂
• 分子量: 140.182
• InChiKey: ZJLOFZQIIMMISY-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 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：

  (S)-5-5(2-methylprop-1-en-1-yl)dihydrofuran-2(3H)-one 在 水 、 potassium carbonate 作用下， 以 甲醇 、 乙醚 、 水 、 溶剂黄146 为溶剂， 生成 (S)-4-Hydroxy-6-methyl-hept-5-enoic acid methyl ester
  参考文献：
  名称：

  偶氮化合物的分子内烯反应合成γ-和δ-内酰胺

  摘要：

  γ-和β-内酰胺很容易从偶氮二羧基物质的分子内烯反应制备。

  DOI：

  10.1016/0040-4039(92)89014-4
• 作为产物：
  描述：

  6-甲基庚-4,5-二烯酸 在 2C₅₀H₅₆O₄P^(1-)*C₇₄H₁₀₄Au₂O₆P₂⁽²⁺⁾ 作用下， 以 水 为溶剂， 反应 12.0h， 以92%的产率得到(S)-5-5(2-methylprop-1-en-1-yl)dihydrofuran-2(3H)-one
  参考文献：
  名称：

  室温下水中不对称金催化内酯化反应

  摘要：

  据报道，不对称金催化的加氢羧化反应具有广泛的底物范围。与原位形成的水性纳米胶束相关的疏水效应使内酯产品具有良好的 ee。烧瓶内产品分离以及催化剂和反应介质的回收相结合，形成了一种特别环保的工艺。

  DOI：

  10.1002/anie.201404729

文献信息

• Silica-Supported Cationic Gold(I) Complexes as Heterogeneous Catalysts for Regio- and Enantioselective Lactonization Reactions
  作者：Xing-Zhong Shu、Son C. Nguyen、Ying He、Fadekemi Oba、Qiao Zhang、Christian Canlas、Gabor A. Somorjai、A. Paul Alivisatos、F. Dean Toste

  DOI：10.1021/jacs.5b04294

  日期：2015.6.10

  catalysts has been developed. These catalysts were easily assembled from readily available silica materials and gold complexes. The heterogeneous catalysts exhibited superior reactivity in various reactions where protodeauration is the rate-limiting step. Dramatic enhancement in regio- and enantioselectivity was observed when compared to the homogeneous unsupported gold catalyst. The catalysts are easily

  已开发出一种合成多相金催化剂的有效方法。这些催化剂很容易由容易获得的二氧化硅材料和金配合物组装而成。多相催化剂在各种反应中表现出优异的反应性，其中原脱氢是限速步骤。与均相无载体金催化剂相比，观察到区域选择性和对映选择性的显着增强。催化剂很容易回收和循环使用多达 11 次而不会损失对映选择性。
• Iridium-Catalyzed C–C Coupling of a Simple Propargyl Ether with Primary Alcohols: Enantioselective Homoaldol Addition via Redox-Triggered (<i>Z</i>)-Siloxyallylation
  作者：Tao Liang、Wandi Zhang、Michael J. Krische

  DOI：10.1021/jacs.5b12131

  日期：2015.12.30

  A chiral iridium complex formed in situ from [Ir(cod)Cl](2) and (R)-H-8-BINAP is found to catalyze the direct enantioselective C C coupling of a simple propargyl ether, TIPSOCH2C CH, with primary alcohols to form gamma-hydroxy (Z)-enol silanes with uniformly high enantioselectivity and complete alkene (Z)-stereo-selectivity. As corroborated by deuterium labeling studies, these studies represent the first examples of 1,2-hydride shift-enabled pi-allyl formation in the context of iridium catalysis.
• TOTAL SYNTHESIS OF (+)-HETEROPLEXISOLIDE E
  作者：Takao Saito、Noriki Kutsumura、Akito Kiriseko

  DOI：10.3987/com-12-s(n)91

  日期：——

  Total synthesis of (+)-heteroplexisolide E has been demonstrated. The synthetic approach exploits the one-pot regioselective Negishi coupling (methylation) and transformation of a beta-methallyl alcohol moiety to a branched prenyl group via palladium-catalyzed hydrogenolysis. For the introduction of the 4-oxo-pentylidene side chain, two independent methods were devised: olefin cross metathesis (CM) (route A) and aldol condensation (route B).
• Asymmetric, Organocatalytic Bromolactonization of Allenoic Acids
  作者：Ulrich Hennecke、Michael Wilking、Constantin Daniliuc

  DOI：10.1055/s-0034-1378278

  日期：——

  Asymmetric, reagent-controlled bromolactonizations of allenoic acids have been achieved by using (DHQD)(2)PHAL as catalyst. A range of substrates can be cyclized in good yields and moderate to good enantioselectivities under operationally simple conditions.
• Conformational analysis of δ-lactams
  作者：Nicolas Boudreault、Richard G. Ball、Christopher Bayly、Michael A. Bernstein、Yves Leblanc

  DOI：10.1016/s0040-4020(01)85279-0

  日期：1994.1

  delta-lactams substituted at C-5 by an oxygen atom exist, in solution principally, in the axial conformation. This axial preferred form is also present in the solid state.