5-methyl-3a,4,7,7a-tetrahydro-3H-isobenzofuran-1-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异苯并呋喃
• 英文名称: 5-methyl-3a,4,7,7a-tetrahydro-3H-isobenzofuran-1-one
• 英文别名: (3aR,7aS)-5-methyl-3a,4,7,7a-tetrahydro-3H-2-benzofuran-1-one
• 化学式: C₉H₁₂O₂
• 分子量: 152.193
• InChiKey: LSUXLXBXMAGQDH-YUMQZZPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  cis-3a,4,7,7a-tetrahydro-5-methyl-1,3-isobenzofurandione 在 titanium(IV) isopropylate 、 4-methyl-cyclohex-4-ene-1,2-dicarboxylic acid-1-isopropyl ester 、 三乙基硼氢化锂 、 (-)-2,3-O-异亚丙基-1,1,4,4-四(2-萘)-l-异赤醇 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 150.0h， 生成 5-methyl-3a,4,7,7a-tetrahydro-3H-isobenzofuran-1-one
  参考文献：
  名称：

  Ti-TADDOLate介导的酯化反应拆分外消旋羧酸衍生物-制备对映体纯化合物的一般方法

  摘要：

  描述了路易斯酸介导的醇盐配体从Ti-TADDOLates 1的手性配体球到环状羧酸衍生物的转移。Ti-TADDOLates可以动力学拆分二恶唑酮，氮杂内酯和联芳基内酯，重结晶后可得到高度对映体富集形式的酯产物（er≥97：3）。Ti-TADDOLate可以使手性环酐的对映异构体开环反应高度对映选择性地产生两个结构异构体。

  DOI：

  10.1016/s0040-4020(97)00456-0

文献信息

• Diels−Alder Reactions of Cyclic Isoimidium Salts
  作者：Robert K. Boeckman、Yan Miller、Todd R. Ryder

  DOI：10.1021/ol101831b

  日期：2010.10.15

  Diels−Alder reactions of cyclic isoimidium salts are described. The corresponding cycloadducts are obtained with high regio- and stereoselectivity. The use of homochiral cyclic isoimidium salts delivers cycloadducts with excellent diastereoselectivity (>99:1) that can be efficiently converted to enantiomerically pure lactones.

  描述了环状异亚胺盐的狄尔斯-阿尔德反应。以高的区域选择性和立体选择性获得了相应的环加合物。高手性环状异亚胺盐的使用可提供具有出色的非对映选择性（> 99：1）的环加合物，可将其有效转化为对映体纯的内酯。
• Bis-aluminated triflic amide promoted Diels–Alder reactions of α,β-unsaturated lactones
  作者：Akio Saito、Hikaru Yanai、Takeo Taguchi

  DOI：10.1016/j.tetlet.2004.10.079

  日期：2004.12

  The bis-aluminated triflic amides such as TfN[Al(Me)Cl](2) and TfN[Al(iBU)(2)](2,) which are derived from triffic amide (I mol) and aluminum reagent (2 mol), can efficiently promote the Diels-Alder reaction of alpha, beta-unsaturated lactone derivatives as dienophiles. Selection of the ligand on aluminum of these Lewis acids should be important depending on the combination of dienophile and 1,3-diene. (C) 2004 Elsevier Ltd. All rights reserved.
• Development of effective Lewis acids for the catalytic Diels–Alder reaction of α,β-unsaturated lactones with cyclopentadiene
  作者：Hikaru Yanai、Arata Takahashi、Takeo Taguchi

  DOI：10.1016/j.tetlet.2007.02.131

  日期：2007.4

  We found that 'Tf2CH2 + Me3Al' systems are effective catalytic systems for the DA reaction of less reactive alpha,beta-unsaturated lactone derivatives, compared to alpha,beta,-unsaturated ester derivatives, with cyclopentadiene. Mononuclear aluminum methide complex, Tf2CHAlMe2, as an active species is formed in these catalytic systems. Effects of lactone ring-size on the reactivity and stereoselectivity were also examined. By expanding ring-size, reactivity of alpha,beta-unsaturated lactones reduced but endo-selectivity notably increased. (c) 2007 Elsevier Ltd. All rights reserved.
• Resolution of racemic carboxylic acid derivatives by Ti-TADDOLate mediated esterification reactions—A general method for the preparation of enantiopure compounds
  作者：Dieter Seebach、Georg Jaeschke、Konstanze Gottwald、Keiji Matsuda、Roberto Formisano、David A Chaplin、Matthias Breuning、Gerhard Bringmann

  DOI：10.1016/s0040-4020(97)00456-0

  日期：1997.6

  transfer of an alkoxide ligand from the chiral ligand sphere of Ti-TADDOLates 1 to cyclic carboxylic acid derivatives is described. The kinetic resolution of dioxolanones, azlactones and biaryl lactones by the Ti-TADDOLates affords, after recrystallization, ester products in highly enantioenriched form (er ≥ 97:3). The enantiomer-differentiating ring-opening of a chiral cyclic anhydride by a Ti-TADDOLate

  描述了路易斯酸介导的醇盐配体从Ti-TADDOLates 1的手性配体球到环状羧酸衍生物的转移。Ti-TADDOLates可以动力学拆分二恶唑酮，氮杂内酯和联芳基内酯，重结晶后可得到高度对映体富集形式的酯产物（er≥97：3）。Ti-TADDOLate可以使手性环酐的对映异构体开环反应高度对映选择性地产生两个结构异构体。