1,1-diacetoxy-1-(4-i-propylphenyl)methane | 7154-10-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 1,1-diacetoxy-1-(4-i-propylphenyl)methane
• 英文别名: 4-isopropylbenzal diacetate；4-(isopropyl)phenylmethylene diacetate；1-diacetoxymethyl-4-isopropyl-benzene；Cuminal-diacetat；1-Diacetoxymethyl-4-isopropyl-benzol；[Acetyloxy-(4-propan-2-ylphenyl)methyl] acetate
• CAS: 7154-10-1
• 化学式: C₁₄H₁₈O₄
• 分子量: 250.295
• InChiKey: MLSOUBLMNULAPA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,1-diacetoxy-1-(4-i-propylphenyl)methane 在 saccharin sulfonic acid 作用下， 反应 0.03h， 以90%的产率得到4-异丙基苯甲醛
  参考文献：
  名称：

  糖精磺酸作为 1,1-二乙酸酯制备和脱保护的高效催化剂

  摘要：

  用于官能团转化的方法的选择取决于其简单性、所需产物的高收率、反应时间短、工艺成本低和后处理程序的简便性。为了保护醛，通常优选形成酰基，因为其易于制备以及所产生的 1,1-二乙酸酯在碱性和中性条件下的稳定性。

  DOI：

  10.5012/bkcs.2010.31.8.2399
• 作为产物：
  描述：

  乙酸酐 、 4-异丙基苯甲醛 在 saccharin sulfonic acid 作用下， 反应 1.0h， 以85%的产率得到1,1-diacetoxy-1-(4-i-propylphenyl)methane
  参考文献：
  名称：

  糖精磺酸作为 1,1-二乙酸酯制备和脱保护的高效催化剂

  摘要：

  用于官能团转化的方法的选择取决于其简单性、所需产物的高收率、反应时间短、工艺成本低和后处理程序的简便性。为了保护醛，通常优选形成酰基，因为其易于制备以及所产生的 1,1-二乙酸酯在碱性和中性条件下的稳定性。

  DOI：

  10.5012/bkcs.2010.31.8.2399

文献信息

• Application of Poly(Vinylbenzyltrimethylammonium Tribromide) Resin as an Efficient Polymeric Catalyst in the Acetalization and Diacetylation of Benzaldehydes
  作者：Zubiao Zheng、Bingbing Han、Junjun Hu、Xianwei Li

  DOI：10.2174/1570178617999200718002933

  日期：2021.3

  applications of a new supported tribromide reagent (poly(vinylbenzyltrimethylammonium tribromide) resin) were reported. This supported tribromide resin was used as a catalyst in the acetalization and diacetylation of benzaldehydes under mild conditions with high efficiency. The effects of solvents, and amount of the supported tribromide resin on the reactions were investigated. Under the optimal conditions

  报道了一种新型的负载型三溴化试剂（聚（乙烯基苄基三甲基铵三溴化铵）树脂）的应用。该负载的三溴化物树脂在温和条件下高效地用作苯甲醛的缩醛化和二乙酰化的催化剂。研究了溶剂的影响以及负载的三溴化物树脂的量对反应的影响。在最佳条件下，苯甲醛的缩醛和1,1-二乙酸酯的大部分以优异的收率选择性地获得。
• Green procedures for the chemoselective synthesis of acylals and their cleavage promoted by recoverable sulfonic acid based nanoporous carbon (CMK-5-SO3H)
  作者：DARYOUSH ZAREYEE、EHSAN MIRZAJANZADEH、MOHAMMAD ALI KHALILZADEH

  DOI：10.1007/s12039-015-0884-0

  日期：2015.7

  A selective synthesis of gem-diacetates from the reaction of aldehydes and acetic anhydride in the presence of recyclable nanoporous solid sulfonic acid (CMK-5-SO3H) under solvent-free reaction conditions is reported. The catalyst was also found to be highly active for deprotection of resulting acylals in water.

  报道了一种在无溶剂反应条件下，使用可回收的纳米多孔固体磺酸（CMK-5-SO3H）作为催化剂，从醛和乙酸酐反应中选择性合成二乙酸酯的方法。研究发现，该催化剂对水中的所得乙缩醛脱保护反应也具有高度活性。
• Tungstosulfonic acid as an efficient solid acid catalyst for acylal synthesis for the protection of the aldehydic carbonyl group
  作者：Reddi Mohan Naidu Kalla、Mi Ri Kim、Yu Na Kim、Il Kim

  DOI：10.1039/c5nj02697k

  日期：——

  Tungstosulfonic acid (TSA) has been found to be an efficient solid acid catalyst for the protection of aldehydic carbonyl groups by geminal diacetate (acylal) formation following the nucleophilic addition of acetic anhydride under neat conditions as well as in a solvent. The TSA catalyst is fully characterized by infrared spectroscopy, wide-angle X-ray scattering analysis, and scanning electron microscopy

  钨磺酸（TSA）被发现是在纯净条件下以及在溶剂中亲核加成乙酸酐后通过双乙酸双酯（酰基）的形成来保护醛羰基的有效固体酸催化剂。TSA催化剂的特征在于红外光谱，广角X射线散射分析以及具有能量色散X射线光谱的扫描电子显微镜。在相似的条件下，也已经研究了将酰基脱保护为相应的醛。该催化剂可以重复使用七次而不会显着降低活性。此外，无需色谱分离即可获得所需的产物。该方法是在酮存在下对醛进行化学选择性保护的绿色方法。
• Lithium Trifluoromethanesulfonate (LiOTf) as a Recyclable Catalyst for Highly Efficient Acetylation of Alcohols and Diacetylation of Aldehydes under Mild and Neutral Reaction Conditions
  作者：Babak Karimi、Jafar Maleki

  DOI：10.1021/jo026678+

  日期：2003.6.1

  A variety of alcohols and aldehydes were reacted with acetic anhydride at room temperature in the presence of a catalytic amount of lithium triflate (LiOTf) to produce the corresponding esters and 1,1-diacetates, respectively, in good to excellent yields under essentially neutral reaction conditions. Sensitive functional groups such as PhCO2-, OMe, and OTBDMS ethers survived intact under the described reaction conditions.
• Synthesis of chlorinated alkylbibenzyls and 9-chlororetene
  作者：Tapio Nevalainen

  DOI：10.1016/0045-6535(94)00445-z

  日期：1995.3

  The synthesis of chlorinated alkylbibenzyls and 9-chlororetene is described. These compounds were sythesized for use as model compounds in analytical and toxicological characterization. The structures of the synthesized model compounds found to be very similar to those identified in pulp mill effluent and products. The H-1 NMR and mass spectral data for the compounds are also reported.