Tert-butyl [3-hydroxy-4-(3-methylbut-2-enyl)phenyl] carbonate | 346433-57-6

• 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: Tert-butyl [3-hydroxy-4-(3-methylbut-2-enyl)phenyl] carbonate
• CAS: 346433-57-6
• 化学式: C₁₆H₂₂O₄
• 分子量: 278.348
• InChiKey: TZDWKDYXSFTECM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Tert-butyl [3-hydroxy-4-(3-methylbut-2-enyl)phenyl] carbonate 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 、 间氯过氧苯甲酸 、 lithium hydroxide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 41.0h， 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：

  二碳酸二叔丁酯 在 sodium tetrahydroborate 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醚 、 水 为溶剂， 反应 4.17h， 生成 Tert-butyl [3-hydroxy-4-(3-methylbut-2-enyl)phenyl] carbonate
  参考文献：
  名称：

  生成邻醌甲基化物的温和阴离子方法：邻官能化酚的简便制备物。

  摘要：

  描述了一种生成邻醌甲基化物的低温方法，其允许在低温下容易地将各种R取代基引入芳基环系统上。该方法对于有效制备邻环烷基化的酚是有用的。

  DOI：

  10.1021/jo001752e

文献信息

• A Mild Anionic Method for Generating <i>o-</i>Quinone Methides:  Facile Preparations of <i>Ortho</i>-Functionalized Phenols
  作者：Ryan M. Jones、Ryan W. Van De Water、Christopher C. Lindsey、Christophe Hoarau、Thay Ung、Thomas R. R. Pettus

  DOI：10.1021/jo001752e

  日期：2001.5.1

  A low-temperature method for generating o-quinone methides is described which permits facile introduction of assorted R substituents onto the aryl ring system at low temperature. The method is useful for the efficient preparation of ortho-ring-alkylated phenols.

  描述了一种生成邻醌甲基化物的低温方法，其允许在低温下容易地将各种R取代基引入芳基环系统上。该方法对于有效制备邻环烷基化的酚是有用的。
• The first total synthesis of moracin O and moracin P, and establishment of the absolute configuration of moracin O
  作者：Navneet Kaur、Yan Xia、Yinglan Jin、Nguyen Tien Dat、Kondaji Gajulapati、Yongseok Choi、Young-Soo Hong、Jung Joon Lee、Kyeong Lee

  DOI：10.1039/b823340c

  日期：——

  The first total synthesis of the naturally occurring benzofurans, moracins O and P was achieved using a Sonogashira cross coupling reaction followed by in situ cyclization, and the absolute configuration of natural moracin O was established.

  利用 Sonogashira 交叉偶联反应和原位环化，首次实现了天然苯并呋喃、吗拉辛 O 和 P 的全合成，并确定了天然吗拉辛 O 的绝对构型。
• 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。
• [EN] NOVEL COUMARIN-BASED COMPOUNDS, PREPARATION METHOD THEREOF, AND MULTIDRUG RESISTANCE INHIBITORY PHARMACEUTICAL COMPOSITIONS CONTAINING SAME AS ACTIVE INGREDIENTS<br/>[FR] NOUVEAUX COMPOSÉS À BASE DE COUMARINE, PROCÉDÉ DE PRÉPARATION DE CES DERNIERS ET COMPOSITIONS PHARMACEUTIQUES INHIBANT LA RÉSISTANCE PLÉIOTROPE CONTENANT CES NOUVEAUX COMPOSÉS EN TANT QU'INGRÉDIENTS ACTIFS
  申请人：KOREA RES INST OF BIOSCIENCE

  公开号：WO2010064817A2

  公开（公告）日：2010-06-10

  본 발명은 신규 쿠마린계 화합물, 이의 제조방법 및 이를 유효성분으로 함유하는 다약제내성 억제용 약학적 조성물에 관한 것으로, 본 발명에 따른 쿠마린계 화합물은 다약제내성의 주요 원인인 P-당단백질(P-glycoprotein, Pgp)의 과발현에 대한 억제활성 및 항암제와의 병용투여시 항암활성의 증가를 나타내어 항암제에 대한 다약제내성 극복제제, 치료제 또는 조절제로 이용될 수 있으며, 항암제의 효과를 증진시켜 암환자의 생존률을 높일 수 있고, 병용투여하는 항암제의 용량을 줄여 정상세포에 대한 부작용을 감소시킬 수 있으므로 항암치료에 유용하게 사용될 수 있다.
• Hoarau, Christophe; Pettus, Thomas R.R., Synlett, 2003, # 1, p. 127 - 137
  作者：Hoarau, Christophe、Pettus, Thomas R.R.

  DOI：——

  日期：——