(+/-)-trans-6-(1,1-dimethylethyl)-octahydro-2H-1-benzopyran-2-one | 21197-51-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (+/-)-trans-6-(1,1-dimethylethyl)-octahydro-2H-1-benzopyran-2-one
• 英文别名: 6α-tert-butyl-1-oxa-9α,10β-decal-2-one；1-oxa-6-tert-butyl-2-decalone；(4aR,6R,8aR)-6-tert-butyl-3,4,4a,5,6,7,8,8a-octahydrochromen-2-one
• CAS: 21197-51-3；23201-41-4；23201-42-5；81379-99-9
• 化学式: C₁₃H₂₂O₂
• 分子量: 210.316
• InChiKey: IPKVISRDFCIXEA-GMTAPVOTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 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：

  (+/-)-trans-6-(1,1-dimethylethyl)-octahydro-2H-1-benzopyran-2-one 以 甲酸 为溶剂， 反应 48.0h， 生成 2-tert-butylcyclohexane-1-spiro-4-butyrolactone
  参考文献：
  名称：

  Edward, John T.; Cooke, Ellen; Paradellis, Themistocles C., Canadian Journal of Chemistry, 1981, vol. 59, p. 597 - 600

  摘要：

  DOI：
• 作为产物：
  描述：

  4-叔丁基环己酮N,N-二甲基腙 在 正丁基锂 、 samarium diiodide 、 Amberlyte IR 120 、 异丙硫醇 作用下， 以 四氢呋喃 、 正己烷 、 丙酮 为溶剂， 反应 20.5h， 生成 (+/-)-trans-6-(1,1-dimethylethyl)-octahydro-2H-1-benzopyran-2-one
  参考文献：
  名称：

  通过一锅顺序缩醛化，Tishchenko反应和by离子和硫醇的协同催化内酯化作用，从5-氧代烷醛立体选择性合成δ-内酯。

  摘要：

  通过sa离子和硫醇的协同催化，一系列5-氧代烷醛以有效和立体选择性的方式转化为（取代的）δ-内酯。这一一锅法包括一系列缩醛化，Tishchenko反应和内酯化。与醇相比，有意使用硫醇有利于促进催化循环。提出了反应机理和立体化学，并得到了一些实验证据的支持。sa离子/硫醇共催化反应显示出远程控制的特征，适用于旋光性δ-内酯的不对称合成。这项研究还证明了两种昆虫信息素（2S，5R）-2-甲基己内酯和（R）-十六烷内酯的合成，

  DOI：

  10.1021/jo016058t

文献信息

• Stereochemical studies. X. Synthesis of some epimeric δ-lactones
  作者：Ellen Cooke、Themistocles C. Paradellis、John T. Edward

  DOI：10.1139/v82-006

  日期：1982.1.1

  Stereospecific syntheses are reported for the δ-lactones 3, 5, 8, 17, and 26.

  报道了δ-内酯3、5、8、17和26的立体特异性合成。
• Stereochemical studies. XI. Equilibria between δ-hydroxy-acids and δ-lactones in aqueous tetrahydrofuran. Relative stabilities of isomeric δ-lactones
  作者：John T. Edward、Ellen Cooke、Themistocles C. Paradellis

  DOI：10.1139/v82-367

  日期：1982.10.15

  equilibrium constants K′ for the hydrolysis of 13 δ-lactones to hydroxy-acids in 54% (mol/mol) aqueous tetrahydrofuran at 25 °C have been determined. The equilibrium constants for the isomerization of the five δ-lactones into their epimers, and for the isomerization of their hydroxy-acids into their epimers, have been calculated by the methods of conformational analysis. These calculated values are consistent

  已经确定了 13 δ-内酯在 54% (mol/mol) 四氢呋喃水溶液中在 25°C 水解为羟基酸的平衡常数 K'。五种δ-内酯异构化为差向异构体和羟基酸异构化为差向异构体的平衡常数已通过构象分析方法计算出来。这些计算值与K'的实验值一致。向羟基酸中添加甲基会降低 K'（索普-英戈尔德效应）。
• Cooperative Catalysis of Samarium Diiodide and Mercaptan in a Stereoselective One-Pot Transformation of 5-Oxopentanals into δ-Lactones
  作者：Jue-Liang Hsu、Chao-Tsen Chen、Jim-Min Fang

  DOI：10.1021/ol9911526

  日期：1999.12.1

  [GRAPHICS]We demonstrate a general method for conversion of various 5-oxopentanals to substituted delta-lactones and 1-oxa-2-decalones by the synergistic catalysis of samarium diiodide and 2-propanethiol (or disulfide), The deliberate use of mercaptan is advantageous to facilitate the catalytic cycle, This method shows high stereoselectivities, and an enantioselective procedure is feasible by using the chiral mercaptan (1R,2S)-1 phenyl-2-(N-acetamido)propanethiol as a promoter.
• EDWARD J. T.; COOKE E.; PARADELLIS T. C., CAN. J. CHEM., 1981, 59, NO 3, 597-600
  作者：EDWARD J. T.、 COOKE E.、 PARADELLIS T. C.

  DOI：——

  日期：——
• Baker's yeast reduction of cyclic δ-ketoesters: synthesis and chiroptical properties of condensed δ-lactones
  作者：Cristina Forzato、Patrizia Nitti、Giuliana Pitacco、Ennio Valentin

  DOI：10.1016/s0957-4166(99)00098-1

  日期：1999.4

  Enantiomerically pure condensed delta-lactones have been prepared from the corresponding delta-ketoesters by the use of Saccharomyces cerevisiae. The reactions were not only highly enantioselective but also highly diastereoselective, provided the baker's yeast was preincubated at 50 degrees C for 30 min. Interestingly, and contrary to what is usually found, the use of nutrients inhibited the bioreductions. The relative configurational assignments have been made by means of NMR, while the absolute configurations and conformations of the lactone rings were attributed by means of CD studies. (C) 1999 Elsevier Science Ltd. All rights reserved.