6,7-(methylenedioxy)phthalaldehydic acid | 77632-09-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: 6,7-(methylenedioxy)phthalaldehydic acid
• 英文别名: 6-hydroxy-6H-furo[3,4-g][1,3]benzodioxol-8-one
• CAS: 77632-09-8
• 化学式: C₉H₆O₅
• 分子量: 194.144
• InChiKey: IWJYMGJFBJSWGN-UHFFFAOYSA-N

物化性质

• 熔点：
  153-155 °C
• 沸点：
  462.6±45.0 °C(Predicted)
• 密度：
  1.699±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6,7-(methylenedioxy)phthalaldehydic acid 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 以94%的产率得到6,7-methylenedioxy-phthalide
  参考文献：
  名称：

  General method for the synthesis of phthalaldehydic acids and phthalides from o-bromobenzaldehydes via ortho-lithiated aminoalkoxides

  摘要：

  DOI：

  10.1021/jo00162a011
• 作为产物：
  描述：

  2-溴-3-羟基-4-甲氧基苯甲醛 在 potassium fluoride 、 三氯化铝 作用下， 以 吡啶 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 32.0h， 生成 6,7-(methylenedioxy)phthalaldehydic acid
  参考文献：
  名称：

  General method for the synthesis of phthalaldehydic acids and phthalides from o-bromobenzaldehydes via ortho-lithiated aminoalkoxides

  摘要：

  DOI：

  10.1021/jo00162a011

文献信息

• Central nervous system active compounds. IV. Synthesis of 3-aminobenzylphthalides
  作者：GI Hutchison、PA Marshall、RH Prager、JM Tippett、AD Ward

  DOI：10.1071/ch9802699

  日期：——

  Several 3-aminobenzylphthalides have been prepared by reactions of 3- (2-oxo-1-phenylpropyl)-phthalides with hydrazoic acid or by the Beckmann rearrangement. The corresponding reactions with 3-(2- oxoindanyl)phthalides showed limited success but led to a new synthesis of phthalide-isoquinoline alkaloids. Preliminary biological testing of some of these derivatives indicates that they only have weak central nervous system activity.

  几种 通过 3- (2-氧代-1-苯基丙基)邻苯二甲酸与苯甲酸的反应，或通过贝克曼 重排。与 3-(2-氧代茚基)邻苯二甲酸盐的相应反应 的相应反应显示出有限的成功，但却导致了邻苯二甲酰异喹啉生物碱的新合成。 生物碱。对其中一些衍生物的初步生物测试表明 表明，它们只具有微弱的中枢神经系统活性。
• Unexpected Isomerisation of a Fragment Analogue During Fragment-Based Screening of HIV Integrase Catalytic Core Domain
  作者：John H. Ryan、Karen E. Jarvis、Roger J. Mulder、Craig L. Francis、G. Paul Savage、Olan Dolezal、Thomas S. Peat、John J. Deadman

  DOI：10.1071/ch15587

  日期：——

  Fragment-based screening of human immunodeficiency virus type 1 (HIV) integrase revealed several aromatic carboxylic acid fragment hits, some of which bound weakly at the site on the HIV-integrase catalytic core domain that binds the lens epithelium-derived growth factor (LEDGF). Virtual screening of an internal database identified an analogue that bound with higher affinity and in an isomerised form to the LEDGF binding site. The starting lactone was stable in CDCl3; however, an unexpected isomerisation process occurred in [D6]DMSO to give the same isomer found in the LEDGF binding site. This hit led directly to a series of low-micromolar LEDGF inhibitors and, via a scaffold hop, to a series of allosteric binding site inhibitors.

  对人体免疫缺陷病毒 1 型（HIV）整合酶的片段筛选发现了几种芳香族羧酸片段，其中一些与 HIV 整合酶催化核心结构域上结合晶状体上皮源性生长因子（LEDGF）的位点结合力较弱。通过对内部数据库进行虚拟筛选，发现了一种类似物，它能以异构化形式与 LEDGF 结合位点结合，亲和力更高。起始内酯在 CDCl3 中是稳定的；然而，在 [D6]DMSO 中发生了意想不到的异构化过程，产生了与 LEDGF 结合位点相同的异构体。这一发现直接催生了一系列低微摩尔 LEDGF 抑制剂，并通过支架跳跃催生了一系列异构结合位点抑制剂。
• Short synthesis of noscapine, bicuculline, egenine, capnoidine, and corytensine alkaloids through the addition of 1-siloxy-isobenzofurans to imines
  作者：Maria Del Pilar C. Soriano、Nagula Shankaraiah、Leonardo Silva Santos

  DOI：10.1016/j.tetlet.2010.01.104

  日期：2010.3

  A concise diastereotioselective strategy for the synthesis of noscapine, bicuculiine, and egenine (1a-c), as well as capnoidine and corytensine (2a,b), was developed using diastereoselective addition of 1-siloxy-isobenzofurans 4a and 4b to immium ion 5 in a one-pot approach. The synthesis features the use of imine 13 obtained through Bischler-Napieralsky reaction from airline 11. The addition of ionic liquids as addictives in the reactions afforded erythro configuration in major adduct compounds. The synthetic route can also be applied in the total synthesis of promising tubulin binding agent EM105 (3). (C) 2010 Elseviet Ltd. All rights reserved.
• HUNG, TRAN, V.;MOONEY, B. A.;PRAGER, R. H.;WARD, A. D., AUSTRAL. J. CHEM., 1981, 34, N 1, 151-162
  作者：HUNG, TRAN, V.、MOONEY, B. A.、PRAGER, R. H.、WARD, A. D.

  DOI：——

  日期：——
• SINHABABU, ACHINTYA, K.;BORCHARDT, R. T., J. ORG. CHEM., 1983, 48, N 14, 2356-2360
  作者：SINHABABU, ACHINTYA, K.、BORCHARDT, R. T.

  DOI：——

  日期：——