(2,2-dimethylbenzo[d][1,3]dioxol-5-yl)methanol | 71203-57-1

• 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: (2,2-dimethylbenzo[d][1,3]dioxol-5-yl)methanol
• 英文别名: (2,2-dimethylbenzo[1,3]dioxol-5-yl)methanol；(2,2-dimethyl-benzo[1,3]dioxol-5-yl)-methanol；1,3-Benzodioxole-5-methanol, 2,2-dimethyl-；(2,2-dimethyl-1,3-benzodioxol-5-yl)methanol
• CAS: 71203-57-1
• 化学式: C₁₀H₁₂O₃
• 分子量: 180.203
• InChiKey: VDCMVFQLPRQFSY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 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：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2,2-dimethylbenzo[d][1,3]dioxol-5-yl)methanol 在 manganese(IV) oxide 作用下， 生成 2,2-difluorobenzo[d][1,3]dioxole-5-carbaldehyde
  参考文献：
  名称：

  Oxidative Intramolecular Phenolic Coupling Reaction Induced by a Hypervalent Iodine(III) Reagent:  Leading to Galanthamine-Type Amaryllidaceae Alkaloids

  摘要：

  By extending our oxidative phenol-coupling reactions using a hypervalent iodine(III) reagent, a versatile synthetic procedure for the galanthamine-type Amaryllidaceae alkaloids was accomplished. The first total synthesis of (+/-)-sanguinine and the total syntheses of (+/-)-galanthamine, (+/-)-narwedine, (+/-)-lycoramine, and (+/-)-norgalanthamine were also successfully carried out.

  DOI：

  10.1021/jo9807868
• 作为产物：
  描述：

  ethyl 2,2-dimethylbenzo[1,3]dioxole-5-carboxylate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以83%的产率得到(2,2-dimethylbenzo[d][1,3]dioxol-5-yl)methanol
  参考文献：
  名称：

  肽支架上的模板化发色团组装：结构演变。

  摘要：

  使用带有预编程受体位点的模板在给定位置选择性容纳发色团是工程人工采光系统的一种有吸引力的方法。沉迷于这种思路，这项工作解决了使用黄色，红色和蓝色生色团的量身定制的天线架构的创建，同时利用了三个动态共价反应，即二硫键交换，酰基formation和硼酸酯的形成。通过稳态UV / Vis吸收和荧光光谱学研究了各种结构修饰，例如生色团及其空间组织（距离，方向，顺序）对天线内能量转移的影响。这项系统的研究使发色团与蓝色受体之间的黄色和红色供体的能量转移效率显着提高，分别达到了显着的22％和15％。元动力学模拟表明，天线的构象特性受分子内发色团相互作用的驱动，分子间发色团相互作用迫使α螺旋自身折叠，从而消除了由肽主链中受体侧空间排列的编程所产生的任何影响。

  DOI：

  10.1002/chem.201803205

文献信息

• Fe₂(SO₄)₃·xH₂O on silica: an efficient and low-cost catalyst for the direct nucleophilic substitution of alcohols in solvent-free conditions
  作者：Lingjun Li、Anlian Zhu、Yuqin Zhang、Xincui Fan、Guisheng Zhang

  DOI：10.1039/c3ra45772a

  日期：——

  Fe2(SO4)3·xH2O on silica has been found to be a novel efficient catalyst for the direct nucleophilic substitution of alcohols in solvent-free conditions. In this reaction system, the alcohols can react with various nucleophilic reagents for the convenient construction of C–C bonds and C–N bonds with the benefits of high conversion, no requirement to use excessive amounts of the nucleophile, only a catalytic amount of iron catalyst required, solvent-free and benign reaction conditions, and the feasible reusability of the catalyst.

  研究发现，二氧化硅上的 Fe2(SO4)3-xH2O 是一种新型高效催化剂，可在无溶剂条件下直接进行醇的亲核取代反应。在该反应体系中，醇类可与各种亲核试剂发生反应，方便地构建 C-C 键和 C-N 键，具有转化率高、无需使用过量的亲核剂、只需催化量的铁催化剂、反应条件无溶剂且无害、催化剂可重复使用等优点。
• Synthesis of Catecholate Ligands with Phosphonate Anchoring Groups
  作者：Elaine Seraya、Zhongyue Luan、Matt Law、Alan F. Heyduk

  DOI：10.1021/acs.inorgchem.5b01191

  日期：2015.8.3

  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.
• Sargent, Melvyn V.; Wangchareontrakul, Sirichai; Jefferson, Alan, Journal of the Chemical Society. Perkin transactions I, 1989, # 3, p. 431 - 439
  作者：Sargent, Melvyn V.、Wangchareontrakul, Sirichai、Jefferson, Alan

  DOI：——

  日期：——
• SARGENT, MELVYN V.;WANGCHAREONTRAKUL, SIRICHAI;JEFFERSON, ALAN, J. CHEM. SOC. PERKIN TRANS. PT 1,(1989) N, C. 431-439
  作者：SARGENT, MELVYN V.、WANGCHAREONTRAKUL, SIRICHAI、JEFFERSON, ALAN

  DOI：——

  日期：——
• [EN] MANNOSE 6-PHOSPHATE OR ASGPR RECEPTOR BINDING COMPOUNDS FOR THE DEGRADATION OF EXTRACELLULAR PROTEINS<br/>[FR] COMPOSÉS DE LIAISON AU RÉCEPTEUR MANNOSE-6-PHOSPHATE OU ASGPR POUR LA DÉGRADATION DE PROTÉINES EXTRACELLULAIRES
  申请人：[en]AVILAR THERAPEUTICS, INC.

  公开号：WO2023028338A2

  公开（公告）日：2023-03-02

  Compounds and compositions that have a mannose 6-phosphate receptor or ASGPR binding ligand bound to an extracellular protein binding ligand are provided for the selective degradation of a target extracellular protein in vivo to treat disorders mediated by the extracellular protein.