2-(1-hydroxy-1-methylethyl)-2,3-dihydrobenzofuran-6-ol | 4806-05-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 香豆素
• 英文名称: 2-(1-hydroxy-1-methylethyl)-2,3-dihydrobenzofuran-6-ol
• 英文别名: 2-(1-hydroxy-1-methyl-ethyl)-2,3-dihydro-benzofuran-6-ol；2-<α-Hydroxy-isopropyl>-6-hydroxy-cumaran；2-(α-Hydroxyisopropyl)-6-hydroxycumaran；2-(2-Hydroxypropan-2-yl)-2,3-dihydro-1-benzofuran-6-ol；2-(2-hydroxypropan-2-yl)-2,3-dihydro-1-benzofuran-6-ol
• CAS: 4806-05-7
• 化学式: C₁₁H₁₄O₃
• 分子量: 194.23
• InChiKey: KNGVODGLMAODGT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(1-hydroxy-1-methylethyl)-2,3-dihydrobenzofuran-6-ol 在 吡啶 、 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 pyridine hydrofluoride 、 一氯化碘 、 potassium carbonate 、 溶剂黄146 、 三乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 37.0h， 生成 {4-[6-(1-hydroxy-1-methylethyl)-5,6-dihydrobenzo[1,2-b;5,4-b']difuran-2-yl]phenoxy}acetic acid ethyl ester
  参考文献：
  名称：

  HIF-1α inhibitors: Synthesis and biological evaluation of novel moracin O and P analogues

  摘要：

  The natural products moracins O and P exhibited potent in vitro inhibitory activity against hypoxia-inducible factor (HIF-1), which is a key mediator during adaptation of cancer cells to tumour hypoxia. Systematic variations of the structures of benzofuran type moracins were made and structure-activity relationship analysis showed the importance of the 2-arylbenzofuran ring and the (R)-configuration of the core scaffold. Further evaluation of the representative compound 5 showed its inhibitory effect on HIF-1 alpha protein accumulation and target gene expression under hypoxia. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.03.022
• 作为产物：
  描述：

  Tert-butyl [3-hydroxy-4-(3-methylbut-2-enyl)phenyl] carbonate 在 lithium hydroxide 、 二甲基二环氧乙烷 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 48.17h， 生成 2-(1-hydroxy-1-methylethyl)-2,3-dihydrobenzofuran-6-ol
  参考文献：
  名称：

  由邻戊烯基化酚合成F11334：中性鞘磷脂酶（N-SMase）的μM抑制剂

  摘要：

  F11334A 1，F11334A 2，F11334A 3以及它们相应的间苯二酚类似物与F11334B 1和F11263一起合成。在这些合成研究的过程中，开发了用于操作（2,3-丙二醇）和（2,3-环氧丙基）o-取代酚的几种条件，以及裂解芳基碳酸叔丁酯的各种条件。。从酶分析看来，对苯二酚核是抑制N-SMase必需的必需结构。此外，似乎该化合物家族由不可逆抑制剂组成。

  DOI：

  10.1016/s0040-4020(02)00391-5

文献信息

• Synthesis of the F11334's from o-prenylated phenols: μM inhibitors of neutral sphingomyelinase (N-SMase)
  作者：Christopher C Lindsey、Consuelo Gómez-Dı́az、José M Villalba、Thomas R.R Pettus

  DOI：10.1016/s0040-4020(02)00391-5

  日期：2002.5

  their corresponding resorcinol analogs were synthesized along with F11334B1, and F11263. In the course of these synthetic studies, several conditions for manipulating (2,3-propanediol) and (2,3-epoxypropyl) o-substituted phenols were developed as well as a variety of conditions for cleavage of aryl O-t-butyl carbonates. From enzyme assays it appears that the hydroquinone nucleus is the essential structural

  F11334A 1，F11334A 2，F11334A 3以及它们相应的间苯二酚类似物与F11334B 1和F11263一起合成。在这些合成研究的过程中，开发了用于操作（2,3-丙二醇）和（2,3-环氧丙基）o-取代酚的几种条件，以及裂解芳基碳酸叔丁酯的各种条件。。从酶分析看来，对苯二酚核是抑制N-SMase必需的必需结构。此外，似乎该化合物家族由不可逆抑制剂组成。
• HIF-1α inhibitors: Synthesis and biological evaluation of novel moracin O and P analogues
  作者：Yan Xia、Yinglan Jin、Navneet Kaur、Yongseok Choi、Kyeong Lee

  DOI：10.1016/j.ejmech.2011.03.022

  日期：2011.6

  The natural products moracins O and P exhibited potent in vitro inhibitory activity against hypoxia-inducible factor (HIF-1), which is a key mediator during adaptation of cancer cells to tumour hypoxia. Systematic variations of the structures of benzofuran type moracins were made and structure-activity relationship analysis showed the importance of the 2-arylbenzofuran ring and the (R)-configuration of the core scaffold. Further evaluation of the representative compound 5 showed its inhibitory effect on HIF-1 alpha protein accumulation and target gene expression under hypoxia. (C) 2011 Elsevier Masson SAS. All rights reserved.