3,9-Dimethyl-3,9-diphenyl-2,4,8,10-tetraoxaspiro<5,5>undecan

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,9-Dimethyl-3,9-diphenyl-2,4,8,10-tetraoxaspiro<5,5>undecan
• 英文别名: 3,9-dimethyl-3,9-diphenyl-2,4,8,10-tetraoxaspiro<5.5>undecane；3,9-diphenyl-3,9-dimethyl-2,4,8,10-tetraoxaspiro<5,5>undecane；3,9-dimethyl-3,9-diphenyl-2,4,8,10-tetraoxa-spiro[5.5]undecane；3,9-Dimethyl-3,9-diphenyl-2,4,8,10-tetraoxa-spiro[5.5]undecan；3,9-Diphenyl-3,9-dimethyl-2,4,8,10-tetraoxaspiro[5,5]undecane；3,9-dimethyl-3,9-diphenyl-2,4,8,10-tetraoxaspiro[5.5]undecane
• 化学式: C₂₁H₂₄O₄
• 分子量: 340.419
• InChiKey: JJMSVKOAEPSGJF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,9-Dimethyl-3,9-diphenyl-2,4,8,10-tetraoxaspiro<5,5>undecan 在 溴 作用下， 以 乙醚 为溶剂， 反应 1.0h， 以82%的产率得到3,9-Bis(bromomethyl)-3,9-diphenyl-2,4,8,10-tetraoxaspiro<5.5>undecane
  参考文献：
  名称：

  Zur Stereochemie einiger neuer chiraler Bromverbindungen mit einem 2,4,8,10-Tetraoxaspiro[5.5]-undecan ? Ger�st

  摘要：

  New compounds containing the 2,4,8,10-tetraoxaspiro[5.5] undecanic skeleton, substituted with brominated groups, have been synthesized by a regioselective radicalic bromination reaction. The stereochemistry of the compounds was studied by high resolution NMR methods. The anancomericity or the flipping of the rings was inferred from the conformational analysis. The chirality of the spiranic skeleton was investigated by means of the diastereotopicity of hydrogen and carbon atoms.

  DOI：

  10.1007/bf00811022
• 作为产物：
  描述：

  季戊四醇 、 苯乙酮 在 cellulose sulfuric acid 作用下， 反应 0.37h， 以85%的产率得到3,9-Dimethyl-3,9-diphenyl-2,4,8,10-tetraoxaspiro<5,5>undecan
  参考文献：
  名称：

  纤维素硫酸作为一种高效，可生物降解和可重复使用的催化剂，羰基化合物如季戊四醇二缩醛和二缩酮的乙酰化

  摘要：

  本文报道了一种实用且绿色的方法，在无热溶剂的条件下，使用纤维素硫酸作为可生物降解和可重复使用的固体酸催化剂，将羰基化合物缩醛化为季戊四醇二缩醛和二缩酮衍生物。

  DOI：

  10.1002/cjoc.201280002

文献信息

• 2,4,4,6-Tetrabromo-2,5-cyclohexadienone (TABCO), N-Bromosuccinimide (NBS) and Bromine as Efficient Catalysts for Dithioacetalization and Oxathioacetalization of Carbonyl Compounds and Transdithioacetalization Reactions
  作者：Nasser Iranpoor、Habib Firouzabadi、Hamid Reza Shaterian、M. A. Zolfigol

  DOI：10.1080/10426500211712

  日期：2002.5.1

  6-tetrabromo-2,5-cyclohexadienone (TABCO), N-bromosuccinimide (NBS), and bromine as efficient catalysts for conversion of carbonyl compounds to their cyclic and acyclic dithioacetals and 1,3-oxathiolanes under mild reaction conditions are described. These catalysts are also used for efficient transdithioacetalization of acetals, diacetals, ketals, acylals, enamines, hydrazones, and oximes with high

  使用 2,4,4,6-四溴-2,5-环己二烯酮 (TABCO)、N-溴代琥珀酰亚胺 (NBS) 和溴作为有效催化剂将羰基化合物转化为环状和无环二硫缩醛和 1,3-描述了在温和反应条件下的硫杂环戊烷。这些催化剂还用于在硫醇存在下以高产率有效地将缩醛、二缩醛、缩酮、酰基、烯胺、腙和肟转二硫缩醛。
• 2,4,4,6-Tetrabromo-2,5-cyclohexadienone (TABCO) as a Versatile, Efficient, and Chemoselective Catalyst for the Acetalization and Transacetalization of Carbonyl Compounds, the Preparation of Acetonides from Epoxides and Acylals (1,1-Diacetates) from Aldehydes
  作者：Habib Firouzabadi、Nasser Iranpoor、Hamid Reza Shaterian

  DOI：10.1246/bcsj.75.2195

  日期：2002.10

  The efficient and chemoselective preparation of acetals and ketals from carbonyl compounds, transacetalization reactions, the conversion of epoxides to acetonides, and the preparation of acylals from aldehydes in the presence of catalytic amounts of 2,4,4,6-tetrabromo-2,5-cyclohexadienone (TABCO) are described.

  介绍了在催化量的2,4,4,6-四溴-2,5-环己二烯酮（TABCO）存在下，从羰基化合物高效且化学选择性地制备缩醛和缩酮、缩醛交换反应、环氧化合物转化为乙缩醛以及醛制备酰缩醛的方法。
• <i>N</i>-Bromosuccinimide (NBS) Catalyzed Highly Chemoselective Acetalization of Carbonyl Compounds Using Silylated Diols and Pentaerythritol under Neutral Aprotic Conditions
  作者：Babak Karimi、Hassan Hazarkhani、Jafar Maleki

  DOI：10.1055/s-2004-837291

  日期：——

  Various types of carbonyl compounds are efficiently convened to their 1,3-dioxanes and pentaerythritol diacetals by the use of either 1,3-bistrimethylsiloxy propane (A) or 1,3-bistrimethylsilanyloxy-2,2-bistrimethylsilanyloxymethyl propane (D) and a catalytic amount of N-bromosuccinimide (3-10 mol%) under essentially neutral aprotic condition, respectively. A variety of functionalities such as both

  通过使用 1,3-双三甲基甲硅烷氧基丙烷 (A) 或 1,3-双三甲基硅烷氧基-2,2-双三甲基硅烷氧基甲基丙烷 (D) 和分别在基本中性非质子条件下催化量的 N-溴代琥珀酰亚胺 (3-10 mol%)。在目前的反应条件下，脂肪族和酚类-OTBDMS、-OMe、-OBz、呋喃环、双键和更显着的酚类-OTHP 等多种官能团仍然存在。使用本协议还实现了两种 α-叔酮向其环状缩醛的有效转化。
• A new approach to the synthesis of diacetals (diketals) pentaerythritol catalyzed by SO3H-functionalized ionic liquids
  作者：Yuan Yuan Wang、Yan Nan Xu、Zhi Zhong Wang、Li Yi Dai

  DOI：10.1016/j.cclet.2009.12.014

  日期：2010.5

  and environmentally friendly approach to the synthesis of diacetals (diketals) pentaerythritol using SO3H-functionalized ionic liquids (ILs) as catalysts was reported. The ILs show high catalytic activity and reusability with good to excellent yields of the desired products. Hammett method has been used to determine the acidity order of these ionic liquids and the results are consistent with the catalytic

  在本文中，报告了一种使用SO 3 H-官能化离子液体（ILs）作为催化剂合成二缩醛（二缩醛）季戊四醇的有效，简单和环境友好的方法。IL表现出高催化活性和可重复使用性，并具有所需产品的良好或优异的收率。哈米特方法已被用来确定这些离子液体的酸度顺序，其结果与缩醛化反应中观察到的催化活性是一致的。使用[PSPy] [OTf]作为催化剂观察到最大产物产率为93％，并且可以重复使用至少8次而没有明显的活性损失。
• Montmorillonite Clays Catalysis. Part 12.1 An Efficient and Practical Procedure for Synthesis of Diacetals from 2,2-Bis(hydroxymethyl)propane-1,3-diol with Carbonyl Compounds
  作者：Zhan-Hui Zhang,、Tong-Shuang Li、Tong-Shou Jin、Ji-Tai Li

  DOI：10.1039/a803046d

  日期：——

  Preparation of diacetals from 2,2-bis(hydroxymethyl)propane-1,3-diol with aldehydes and ketones is catalysed by montmorillonite clays in refluxing benzene or toluene in good to excellent yield.

  用 aldehydes 和 ketones 制备 2,2-bis(hydroxymethyl)propane-1,3-diol 的二缩醛，在回流的苯或甲苯中以蒙脱石粘土作为催化剂，产率良好至优秀。