2-(benzo[d][1,3]dioxol-5-yl)-4,4-dimethyl-4,5-dihydrooxazole | 85588-72-3

• 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-(benzo[d][1,3]dioxol-5-yl)-4,4-dimethyl-4,5-dihydrooxazole
• 英文别名: 4,4-Dimethyl-2-(3,4-methylenedioxyphenyl)-1,3-oxazoline；2-(1,3-benzodioxol-5-yl)-4,4-dimethyl-5H-1,3-oxazole
• CAS: 85588-72-3
• 化学式: C₁₂H₁₃NO₃
• 分子量: 219.24
• InChiKey: JSCFKPALBRZAOL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  40
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(benzo[d][1,3]dioxol-5-yl)-4,4-dimethyl-4,5-dihydrooxazole 在 aluminum oxide 、 N-氯代丁二酰亚胺 、 二异丁基氢化铝 作用下， 以 乙醚 为溶剂， 反应 9.83h， 生成 胡椒醛
  参考文献：
  名称：

  Reductive cleavage of aryl oxazolines to benzaldehydes and substituted toluenes

  摘要：

  DOI：

  10.1021/jo00170a036
• 作为产物：
  描述：

  胡椒酸 在 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 10.0h， 生成 2-(benzo[d][1,3]dioxol-5-yl)-4,4-dimethyl-4,5-dihydrooxazole
  参考文献：
  名称：

  对 2-(恶唑啉基)-苯酚和 1,2,5-硫属二唑环化衍生物的取代效应：发射颜色可调、极简激发态分子内质子转移 (ESIPT) 基发光体

  摘要：

  合成了被不同给电子和吸电子基团取代的简约 2-(恶唑啉基)-苯酚及其 1,2,5-硫属二唑环化衍生物，并研究了它们在溶液和固体中的发射行为状态。根据引入的取代基的性质及其位置，发射效率会增加或减少，从而产生 AIE 或 ACQ 特性。单晶分析揭示了 J 型和 H 型包装基序以及迄今为止未描述的以酮形式分离的基于 ESIPT 的荧光团。

  DOI：

  10.1021/acs.joc.1c00846

文献信息

• A unified total synthesis of benzo[<i>d</i>][1,3]dioxole-type benzylisoquinoline alkaloids of aporphines, coptisines, and dibenzopyrrocolines
  作者：Jie Lv、Zhi-Hong Li、An-Jun Deng、Hai-Lin Qin

  DOI：10.1039/d1ob02258j

  日期：——

  The first total synthesis of (S)-(+)-ovigerine, (S)-(+)-N-formylovigerine, and (6aS,6a’S)-(+)-ovigeridimerine of aporphine alkaloids with a benzo[d][1,3]dioxole structure feature was established. The strategy was based upon the well-known Pd-catalyzed arylation to set the aporphine framework, and Noyori asymmetric hydrogenation followed by diastereoselective resolution to achieve excellent enantioselectivity

  首次全合成( S )-(+)-卵黄黄碱、( S )-(+)- N-甲酰黄绿素和(6a S ,6a' S )-(+)-鸟黄苷与苯并[ d ][1,3]二氧戊环结构特征建立。该策略基于众所周知的 Pd 催化芳基化来设置阿卟啉骨架，以及 Noyori 不对称氢化，然后进行非对映选择性拆分以实现出色的对映选择性。通过稍微修改总合成路线并将其与 aza-Michael 加成、Bischler-Napieralski 反应和N-芳基化策略性地结合起来，该方法也适用于苯并[ d][1,3]二氧杂环戊烯型苯甲基异喹啉类黄连碱类和二苯并吡咯啉类生物碱，包括黄连碱类的两种凤仙花、四氢黄连碱、溴化黄连季碱和两种二苯并吡咯啉类似物，均能高效合成这些目标化合物。在合成的9种化合物中，首次报道了三种阿朴啡和两种凤仙花的总合成，ee值均大于99%。这项工作也代表了苯并[ d ][1,3]二氧杂环戊烯类阿卟啉、黄连素和二苯并吡咯啉全合成合成路线的首次统一。
• Anti-inflammatory benzylselenobenzamides made from anilines and
  申请人：A. Nattermann & Cie. GmbH

  公开号：US05141955A1

  公开（公告）日：1992-08-25

  Anti-inflammatory benzylselanobenzamides made from anilines and benzylamines have the formula I ##STR1## are disclosed wherein R is hydrogen, methyl or ethyl; R.sup.1 and R.sup.2 are the same or different and, taken separately, are hydrogen, fluorine, chlorine, bromine, C.sub.1 to C.sub.4 alkyl, C.sub.1 to C.sub.4 alkoxy, hydroxy, cyano, amino, dimethylamino or nitro; and R.sup.3 and R.sup.4 are the same or different and, taken separately, are hydrogen, fluorine, chlorine, bromine, C.sub.1 to C.sub.4 alkyl, C.sub.1 to C.sub.4 alkoxy, hydroxy, cyano, or nitro and, taken together, represent methylenedioxy; and n is 0.1 or 2.

  由苯胺和苄胺制成的抗炎苄硒苯甲酰胺具有以下结构式I的化学式，其中R为氢、甲基或乙基；R.sup.1和R.sup.2相同或不同，分别为氢、氟、氯、溴、C.sub.1至C.sub.4烷基、C.sub.1至C.sub.4烷氧基、羟基、氰基、氨基、二甲胺基或硝基；R.sup.3和R.sup.4相同或不同，分别为氢、氟、氯、溴、C.sub.1至C.sub.4烷基、C.sub.1至C.sub.4烷氧基、羟基、氰基或硝基，或者一起表示亚甲二氧基；n为0.1或2。
• Aerobic C(sp²)–H Hydroxylations of 2-Aryloxazolines: Fast Access to Excited-State Intramolecular Proton Transfer (ESIPT)-Based Luminophores
  作者：Dominik Göbel、Nils Clamor、Enno Lork、Boris J. Nachtsheim

  DOI：10.1021/acs.orglett.9b01350

  日期：2019.7.19

  The direct hydroxylation of 2-aryloxazolines via a deprotonative magnesiation using TMPMgCl center dot LiCl and subsequent oxidation with molecular oxygen or air as a green oxidant is reported. This method proceeds under mild conditions at room temperature with high regioselectivity and chemoselectivity. The obtained phenols exhibit tunable luminescence properties, induced by excited-state intramolecular proton transfer. This method opens a new opportunity for the sustainable synthesis of luminescent organic molecules.
• Mazindol Analogues as Potential Inhibitors of the Cocaine Binding Site at the Dopamine Transporter
  作者：William J. Houlihan、Lawrence Kelly、Jessica Pankuch、Judith Koletar、Leonard Brand、Aaron Janowsky、Theresa A. Kopajtic

  DOI：10.1021/jm010302r

  日期：2002.9.1

  A series of mazindol. (2) and homomazindol (3) analogues with a variety of electron-donating and electron-withdrawing groups in the pendant aryl group and the benzo ring C, as well as H, methoxy, and alkyl groups replacing the hydroxyl group were synthesized, and their binding affinities at the dopamine transporter (DAT) on rat or guinea pig striatal. membranes were determined. Several active analogues were also evaluated for their ability to block uptake of DA, 5-HT, and NE and inhibit binding of [I-125] RTI-55 at HEK-hDAT, HEK-hSERT, and HEK-hNET cells. Mazindane (26) was found to be a pro-drug, oxidizing (5-H --> 5-OH) to mazindol on rat striatal membranes and HEk-hDAT cells. The 4',7,8-trichloro analogue (38) of mazindol was the I most potent and selective ligand. for HEK-hDAT cells (DAT K-i = 1.1 nM; SERT/DAT 1283 and NET/DAT = 38). Experimental results strongly favor the cyclic or ol tautomers of 2 and 3 to bind more, tightly at the DAT than the corresponding keto tautomers.
• Takano, Seiichi; Numata, Hirotoshi; Ogasawara, Kunio, Heterocycles, 1983, vol. 20, # 3, p. 417 - 420
  作者：Takano, Seiichi、Numata, Hirotoshi、Ogasawara, Kunio

  DOI：——

  日期：——