5-(bromomethyl)-2,2-dimethylbenzo[1,3]dioxole | 40003-61-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 5-(bromomethyl)-2,2-dimethylbenzo[1,3]dioxole
• 英文别名: 3,4-isopropylidenedioxybenzyl bromide；3,4-isopropylidenedioxybenzylbromide；3,4-Isopropylidendioxy-benzylbromid；5-(Bromomethyl)-2,2-dimethyl-1,3-benzodioxole
• CAS: 40003-61-0
• 化学式: C₁₀H₁₁BrO₂
• 分子量: 243.1
• InChiKey: OGIUIJXNLGRPJD-UHFFFAOYSA-N

物化性质

• 沸点：
  275.7±9.0 °C(Predicted)
• 密度：
  1.442±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  5-(bromomethyl)-2,2-dimethylbenzo[1,3]dioxole 在 三氯化硼 、 三乙胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 39.0h， 生成
  参考文献：
  名称：

  Synthesis of Catecholate Ligands with Phosphonate Anchoring Groups

  摘要：

  New catecholate ligands containing protected phosphonate anchoring groups in the 4-position of the catecholate ring were synthesized. The catechol 4-diethoxyphosphorylbenzene-1,2-diol, ((Et)phoscat)H-2, was prepared in three steps from pyrocatechol; whereas, the catechol 4-(diethoxyphosphorylmethyl)benzene-1,2-diol, ((Et)Bnphoscat)H-2, containing a methylene spacer between the catecholate ring and phosphonate anchor, was prepared from protocatechuic acid in six linear steps. Both catechol derivatives were further elaborated to their trimethylsilyl-protected counterparts to facilitate their binding to nanocrystalline metal oxides. Electronic spectroscopy and cyclic voltammetry were used to probe the electronic properties of the phosphonate-functionalized catecholates in charge-transfer complexes of the general formula (catecholate)Pd(pdi) (pdi = N,N'-bis(mesityl)phenanthrene-9,10-diimine). These studies show that attachment of the phosphonate anchor directly to the 4-position of the ((Et)phoscat)(2-) ligand significantly perturbs the donor ability of the catecholate ligand; however, incorporation of a single methylene spacer group in ((Et)Bnphoscat)(2-) helps to isolate catecholate from the electron-withdrawing phosphonate group.

  DOI：

  10.1021/acs.inorgchem.5b01191
• 作为产物：
  描述：

  ethyl 2,2-dimethylbenzo[1,3]dioxole-5-carboxylate 在 吡啶 、 lithium aluminium tetrahydride 、 三溴化磷 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 2.0h， 生成 5-(bromomethyl)-2,2-dimethylbenzo[1,3]dioxole
  参考文献：
  名称：

  Synthesis of Catecholate Ligands with Phosphonate Anchoring Groups

  摘要：

  New catecholate ligands containing protected phosphonate anchoring groups in the 4-position of the catecholate ring were synthesized. The catechol 4-diethoxyphosphorylbenzene-1,2-diol, ((Et)phoscat)H-2, was prepared in three steps from pyrocatechol; whereas, the catechol 4-(diethoxyphosphorylmethyl)benzene-1,2-diol, ((Et)Bnphoscat)H-2, containing a methylene spacer between the catecholate ring and phosphonate anchor, was prepared from protocatechuic acid in six linear steps. Both catechol derivatives were further elaborated to their trimethylsilyl-protected counterparts to facilitate their binding to nanocrystalline metal oxides. Electronic spectroscopy and cyclic voltammetry were used to probe the electronic properties of the phosphonate-functionalized catecholates in charge-transfer complexes of the general formula (catecholate)Pd(pdi) (pdi = N,N'-bis(mesityl)phenanthrene-9,10-diimine). These studies show that attachment of the phosphonate anchor directly to the 4-position of the ((Et)phoscat)(2-) ligand significantly perturbs the donor ability of the catecholate ligand; however, incorporation of a single methylene spacer group in ((Et)Bnphoscat)(2-) helps to isolate catecholate from the electron-withdrawing phosphonate group.

  DOI：

  10.1021/acs.inorgchem.5b01191

文献信息

• Synthesis and structure-activity relationships of cephalosporins, 2-isocephems, and 2-oxaisocephems with C-3′ or C-7 catechol or related aromatics
  作者：Koichi Tsuji、Hidetsugu Tsubouchi、Koichi Yasumura、Makoto Matsumoto、Hiroshi Ishikawa

  DOI：10.1016/s0968-0896(96)00217-9

  日期：1996.12

  A series of cephalosporins, 2-isocephems, and 2-oxaisocephems with C-3' catechol-containing (pyridinium-4-thio)methyl groups and 2-isocephems with C-7 catechol related aromatics have been prepared and evaluated for antimicrobial activity. It turns out that these compounds have highly potent activity against Gram-negative bacteria, especially resistant pathogens such as Pseudomonas aeruginosa. The most

  制备了一系列具有C-3'邻苯二酚的（4-吡啶鎓吡啶）甲基的头孢菌素，2-isophephems和2-oxaisocephephe和具有C-7-catechol相关芳香族化合物的2-isophephes，并进行了抗菌活性评估。事实证明，这些化合物对革兰氏阴性菌，特别是铜绿假单胞菌等耐药病原体具有很强的活性。该系列中活性最高的化合物是（6S，7S）-7- [2-（2-氨基噻唑-4-基）-2-[（Z）-[（1,5-二羟基-4-吡啶idon-2 -（基）甲氧基]亚氨基]乙酰胺基] -3-[[[（（4-甲基-5-羧甲基）噻唑-2-基]硫代]甲基] -8-氧代-1-氮杂-4-硫代双环[4.2.0 ]辛-2-烯-2-羧酸，对临床分离的P，铜绿假单胞菌和鲍曼不动杆菌均表现出强大的体外活性，而鲍曼不动杆菌也对许多抗感染药具有耐药性，
• Method of preparing aldehydes
  申请人：Sagami Chemical Research Center

  公开号：US03962281A1

  公开（公告）日：1976-06-08

  A novel method for preparing substituted actaldehydes comprising subjecting a specific sulfoxide derivative to an acidic hydrolysis.

  一种制备取代十四醛的新方法，包括将特定的亚砜衍生物进行酸性水解处理。
• US3962281A
  申请人：——

  公开号：US3962281A

  公开（公告）日：1976-06-08
• US4088667A
  申请人：——

  公开号：US4088667A

  公开（公告）日：1978-05-09
• [EN] LARGE SCALE PRODUCTION OF CATECHOL-CONTAINING POLYMERS<br/>[FR] PRODUCTION À GRANDE ÉCHELLE DE POLYMÈRES CONTENANT DU CATÉCHOL
  申请人：PURDUE RESEARCH FOUNDATION

  公开号：WO2021127079A1

  公开（公告）日：2021-06-24

  This invention relates to a method for manufacturing a catechol-containing co-polymer through a suspension polymerization or a solution polymerization process. In some illustrative embodiments, this disclosure relates to a process of a free radical suspension polymerization for large-scale manufacturing catechol-containing copolymers. In some other illustrative embodiments, this disclosure relates to a solution polymerization of free radical, cationic, or anionic process for large-scale manufacturing catechol-containing copolymers. The process and the product thereof are within the scope of this disclosure.