3,4-dimethoxyphenyl chloroformate | 121750-74-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3,4-dimethoxyphenyl chloroformate
• 英文别名: (3,4-dimethoxyphenyl) carbonochloridate
• CAS: 121750-74-1
• 化学式: C₉H₉ClO₄
• 分子量: 216.621
• InChiKey: WEWQQXOZLOKJKK-UHFFFAOYSA-N

物化性质

• 沸点：
  273.6±25.0 °C(Predicted)
• 密度：
  1.274±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,4-dimethoxyphenyl chloroformate 在 bis(1,5-cyclooctadiene)diiridium(I) dichloride 、 四甲基乙二胺 、 [O,O'-(S)-(1,1'-dinaphthyl-2,2'-diyl)-N,N’-di-(S,S)-1-(2-methoxyphenyl)ethylphosphoramidite] 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 0.5h， 生成 (S)-(+)-1-phenyl-1-(3,4-dimethoxyphenoxy)-2-propene
  参考文献：
  名称：

  Ir（I）催化的对映选择性脱羧烯丙基醚化：芳基烯丙基醚不对称合成的一般方法

  摘要：

  Ir（I）催化的芳基碳酸烯丙酯的对映选择性脱羧烯丙基醚化反应提供了芳基烯丙基醚。反应的一般性和高立体选择的关键是使用分子内脱羧烯丙基化过程和[Ir（dbcot）Cl] 2作为Ir（I）来源。Ir（I）催化的非对映选择性脱羧烯丙基醚化反应，与不对称醛的crotylation和交叉复分解相结合，可以提供具有高非对映选择性的单保护的2-甲基-1,3-二醇（从简单的醛开始）。

  DOI：

  10.1021/ol3033237
• 作为产物：
  描述：

  光气 、 3,4-二甲氧基苯酚 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 苯 为溶剂， 反应 45.0h， 以84%的产率得到3,4-dimethoxyphenyl chloroformate
  参考文献：
  名称：

  1-substituted-1,2,5,6-tetrahydropyridine-3-carboxaldehyde-O-alkyloximes as novel orally active and long-lasting muscarinic cholinergic agonists

  摘要：

  Our previous attempts to design muscarinic agonists related to arecoline with the prerequisites for clinical use were successful with the discovery of 1,2,5,6-tetrahydropyridine-3-carboxaldehyde-O-methyloxime hydrochloride, RU 35963, and structurally related compounds, in which die metabolically labile ester group of arecoline was replaced with the bioisosteric and stable aldoxime group. With the aim of obtaining compounds with improved cholinomimetic properties, several aryl- and alkyl-carbamates of RU 35963, as well as O-alkyl-, and O-aryl-carbamates of the 1-hydroxy-1,2,5,6-tetrahydropyridine-3- carboxaldehyde-O-methyloxime hydrochloride, 24, have been synthesized and evaluated biologically. The most interesting molecules to emerge from the primary screening have been evaluated more extensively and their cholinomimetic profiles compared with those of the parent molecules. In vitro studies indicate that none of these prodrugs have affinity for muscarinic receptor sites and some of them (aryl-carbamates) have cholinesterase inhibiting properties. Results from in vivo experiments in mice and rats showed that these new substances, 1-[4-chlorophenyl] oxycarbonyl-1,2,5,6-tetrahydropyridine-3- carboxaldehyde-O-methyloxime (16 = RU 47213) in particular, have cholinomimetic properties that compare favourably with those of the parent compounds. After oral administration 16 was clearly superior to RU 35963 in terms of central selectivity, duration of action and therapeutic indexes.

  DOI：

  10.1016/0223-5234(92)90186-5

文献信息

• 1,2,5,6-tetrahydropyridine oxime derivatives
  申请人：Beecham Group p.l.c.

  公开号：US05356914A1

  公开（公告）日：1994-10-18

  Compounds of formula (I) or a pharmaceutically acceptable salt thereof: ##STR1## wherein R.sub.1 represents a 1,2,5,6-tetrahydropyridin-3-yl group N-substituted by R.sub.10 wherein R.sub.10 represents OH; a group hydrolysable in vivo to OH or hydrogen; C.sub.1-8 alkoxy; C.sub.2-8 alkenyloxy; C.sub.2-8 alkynyloxy; C.sub.3-8 cycloalkyloxy; or COR.sub.13 wherein R.sub.13 represents hydrogen, C.sub.1-8 alkyl, phenyl or phenyl C.sub.1-4 alkyl; in which any phenyl moiety is optionally substituted by up to 3 substituents independently selected from C.sub.1-6 alkoxy, C.sub.1-6 alkyl, halo, C.sub.1-6 alkoxycarbonyl, cyano, C.sub.1-6 alkylthio or C.sub.1-6 alkylsulphonyl; enhance acetylcholine function via an action at muscarinic receptors within the central nervous system and are therefore of potential use in the treatment and/or prophylaxis of dementia in mammals.

  公式（I）的化合物或其药用盐：其中R.sub.1代表由R.sub.10N取代的1,2,5,6-四氢吡啶-3-基团，其中R.sub.10代表OH；在体内可水解为OH或氢的基团；C.sub.1-8烷氧基；C.sub.2-8烯氧基；C.sub.2-8炔氧基；C.sub.3-8环烷氧基；或COR.sub.13，其中R.sub.13代表氢，C.sub.1-8烷基，苯基或苯基C.sub.1-4烷基；在其中，任何苯基部分可选择性地取代为最多3个独立选择的C.sub.1-6烷氧基，C.sub.1-6烷基，卤素，C.sub.1-6烷氧羰基，氰基，C.sub.1-6烷硫基或C.sub.1-6烷基磺酰基；通过在中枢神经系统内对胆碱能受体的作用增强乙酰胆碱功能，因此在哺乳动物的痴呆症的治疗和/或预防中具有潜在用途。
• From (+)-epigallocatechin gallate to a simplified synthetic analogue as a cytoadherence inhibitor for P. falciparum
  作者：Sandra Gemma、Simone Brogi、Pradeep R. Patil、Simone Giovani、Stefania Lamponi、Andrea Cappelli、Ettore Novellino、Alan Brown、Matthew K. Higgins、Khairul Mustafa、Tadge Szestak、Alister G. Craig、Giuseppe Campiani、Stefania Butini、Margherita Brindisi

  DOI：10.1039/c3ra45933k

  日期：——

  Parasite derived surface antigen PfEMP1 is a virulence factor of the human malaria parasite. PfEMP1 variants have been implicated in the cytoadherence of P. falciparum infected erythrocytes (iRBC) to several binding receptors on host vascular endothelium. Among them, binding to ICAM-1 seems to be related to severe manifestations of the disease such as cerebral malaria. The binding site for iRBC has been mapped to the BED-side of the N-terminal immunoglobulin-like domain of ICAM-1, and the DE-loop appears to be critical for binding. To date (+)-EGCG is the unique small molecule anti-cytoadherence inhibitor probably mimicking the DE-loop of ICAM-1. Here we report the discovery of a tetrahydroisoquinoline derivative, a prototype of a novel class of cytoadherence inhibitors, and an analogue of the natural compound characterized by a synthetically accessible scaffold. Molecular modeling analysis of (+)-EGCG and its synthetic tetrahydroisoquinoline analogue rationalized their binding mode to PfEMP1, confirming their ability to mimic the DE-loop.

  寄生虫表面抗原 PfEMP1 是人类疟原虫的致病因子。PfEMP1变体与恶性疟原虫感染的红细胞（iRBC）与宿主血管内皮上的几种结合受体的细胞粘附有关。其中，与 ICAM-1 的结合似乎与脑疟疾等疾病的严重表现有关。iRBC 的结合位点已被绘制到 ICAM-1 N 端免疫球蛋白样结构域的 BED 侧，DE 环似乎是结合的关键。迄今为止，(+)-EGCG 是唯一可能模拟 ICAM-1 DE 环的小分子抗细胞粘附抑制剂。在此，我们报告了一种四氢异喹啉衍生物的发现，它是一类新型细胞粘附抑制剂的原型，也是一种天然化合物的类似物，其特点是具有可合成的支架。(+)-EGCG及其合成四氢异喹啉类似物的分子建模分析合理地解释了它们与PfEMP1的结合模式，证实了它们模拟DE环的能力。
• 1,2,5,6-TETRAHYDROPYRIDINE OXIME DERIVATIVES
  申请人：BEECHAM GROUP PLC

  公开号：EP0552213A1

  公开（公告）日：1993-07-28
• US4921868A
  申请人：——

  公开号：US4921868A

  公开（公告）日：1990-05-01
• US5231107A
  申请人：——

  公开号：US5231107A

  公开（公告）日：1993-07-27