9-甲基-1,4-二氧杂螺[4.4]壬烷 | 69423-50-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 9-甲基-1,4-二氧杂螺[4.4]壬烷
• 英文名称: ethylene-acetal de la methyl-2 cyclopentanone
• 英文别名: 2-methylcyclopentanone ethylene ketal；6-methyl-1,4-dioxa-spiro[4.4]nonane；6-Methyl-1,4-dioxa-spiro[4.4]nonan；6-Methyl-1,4-dioxaspiro[4.4]nonane；9-methyl-1,4-dioxaspiro[4.4]nonane
• CAS: 69423-50-3
• 化学式: C₈H₁₄O₂
• 分子量: 142.198
• InChiKey: WDUKEYBANYJILV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  9-甲基-1,4-二氧杂螺[4.4]壬烷 在 三氟化硼乙醚 、 sodium hydride 作用下， 以 二乙二醇二甲醚 、 1,2-二氯乙烷 、 mineral oil 为溶剂， 反应 23.0h， 生成
  参考文献：
  名称：

  Lewis Acid Catalyzed α-Functionalization of Ketals for the Regioselective Synthesis of α-Carbamoyl Ketals

  摘要：

  Treatment of 1 with DEAD in the presence of BF3 center dot OEt2 gave 2 (R = H), which was N-alkylated to give 2 (R = CH2CO2Et), and insitu eliminated (E1cb) to give alpha-carbamoyl ketals.

  DOI：

  10.1021/ol301710w
• 作为产物：
  描述：

  2-(pent-4-en-1-yl)-1,3-dioxolane 在 tri-tert-butoxysilanethiol 、 Me-(t-BuO₂)C-Et(DTBPB) 作用下， 以 正辛烷 为溶剂， 反应 2.0h， 以10%的产率得到9-甲基-1,4-二氧杂螺[4.4]壬烷
  参考文献：
  名称：

  Radical-chain cyclisation of unsaturated acetals and thioacetals in the presence of thiols as polarity-reversal catalysts

  摘要：

  Polarity-reversal catalysis by thiols has been applied to promote the radical-chain cyclisation of 2-(pent-4-enyl)-substituted 1,3-dioxolanes, 1,3-dithianes and 1,3-dithiolanes to give spirocyclic products. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01898-5

文献信息

• Transferts d'hydrogènes dans les cations radicaux ethylène-acetals dérivés de cyclopentanones et cyclohexanones
  作者：H. E. Audier、J. C. Tabet、M. Fetizon

  DOI：10.1002/hlca.19850680412

  日期：1985.6.26

  Hydrogen Transfer during Decompositions of Molecular Ions of Acetals Derived from Substituted Cyclopentanones and Cyclohexanones

  缩合环戊酮和环己酮衍生的缩醛缩合分子离子过程中的氢转移
• A remarkable iodine-catalyzed protection of carbonyl compounds
  作者：Bimal K. Banik、Marin Chapa、Jocabed Marquez、Magda Cardona

  DOI：10.1016/j.tetlet.2005.01.176

  日期：2005.3

  report here a remarkably simple molecular iodine-catalyzed protection method for various carbonyl compounds as ketals in a general reaction. The iodine-catalyzed reaction of mandelic acid and lactic acid with several aldehydes has furnished a highly diastereoselective synthesis of cis and trans dioxolanones.

  我们在这里报告了一种在一般反应中作为缩酮的各种羰基化合物的非常简单的分子碘催化的保护方法。扁桃酸和乳酸与几种醛的碘催化反应提供了顺式和反式二氧戊环酮的高度非对映选择性合成。
• Formation of 2,2-disubstituted 1,3-cyclopentanediones from ketals with 1,2-bis(trimethylsilyloxy)cyclobutene
  作者：Yong-Jin Wu、Dean W. Strickland、Tracy J. Jenkins、Pei-Ying Liu、D. Jean Burnell

  DOI：10.1139/v93-169

  日期：1993.9.1

  The direct formation of 2,2-disubstituted 1,3-cyclopentanedione compounds by a Lewis acid catalysed reaction with 1,2-bis(trimethylsilyloxy)cyclobutene proceeds in good to excellent yields with unhindered ketals, but steric hindrance reduces the yields considerably. A carbonyl group α or β to the ketal, or a carbon–carbon double bond α to the ketal, stops the reaction completely. Orthoesters do not give geminally acylated products in synthetically useful yields.

  通过路易斯酸催化的反应，使用1,2-双(三甲基硅氧基)环丁烯与没有受阻碍的缩酮，直接形成2,2-二取代的1,3-环戊二酮化合物，产率良好至优秀，但立体位阻显著降低了产率。位于缩酮α或β位置的羰基，或者与缩酮α位置相邻的碳-碳双键会完全停止反应。正酯不会以合成有用的产率产生双酰化产物。
• Kinetic and Equilibrium Studies of Cyclic Ketal Formation and Hydrolysis^1,2
  作者：Melvin S. Newman、Robert J. Harper

  DOI：10.1021/ja01556a047

  日期：1958.12
• Method of searching substrate having antidiabetic activity
  申请人：Ishiguro Hiroki

  公开号：US20070191402A1

  公开（公告）日：2007-08-16

  The present invention provides a screening method of a substance which inhibits binding of a condensed purine derivative to a pancreatic β cell or a treated product of the cell, a substance which inhibits binding of a condensed purine derivative to a protein capable of the condensed purine derivative, and a substance which inhibits the expression or enzymatic activity of a protein capable of a condensed purine derivative, which comprises using the condensed purine derivative and a pancreatic β cell or a treated product of the cell or a protein capable of binding to the condensed purine derivative.