Tert-butyl [3-[(2-methylpropan-2-yl)oxycarbonyloxy]phenyl] carbonate | 145530-95-6

• 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-[(2-methylpropan-2-yl)oxycarbonyloxy]phenyl] carbonate
• CAS: 145530-95-6
• 化学式: C₁₆H₂₂O₆
• 分子量: 310.347
• InChiKey: UCTHVPVFWHQVHM-UHFFFAOYSA-N

物化性质

• 沸点：
  392.6±38.0 °C(predicted)
• 密度：
  1.122±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Tert-butyl [3-[(2-methylpropan-2-yl)oxycarbonyloxy]phenyl] carbonate 、 联硼酸频那醇酯 在 (1,5-cyclooctadiene)(methoxy)iridium(I) dimer 、 4,4'-二叔丁基-2,2'-二吡啶 作用下， 以 2-甲基戊烷 为溶剂， 反应 18.0h， 生成 Tert-butyl [3-[(2-methylpropan-2-yl)oxycarbonyloxy]-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl] carbonate
  参考文献：
  名称：

  Iridium-catalyzed C–H activation/borylation/oxidation for the preparation of bis-protected phloroglucinol derivatives

  摘要：

  The preparation of bis-protected phloroglucinol derivatives from a range of protected resorcinol substrates is presented. Functionalization was achieved via a two-step, one-pot iridium-catalyzed C-H activation/borylation/oxidation protocol. Our system gave high conversions to the arylboronic esters and good yields of the desired phenols following subsequent oxidation. A range of common protecting group categories was studied including alkyl, silyl, ether and ester. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.03.049
• 作为产物：
  描述：

  二碳酸二叔丁酯 、 间苯二酚 以 neat (no solvent) 为溶剂， 反应 0.05h， 以85%的产率得到tert-butyl (3-hydroxyphenyl) carbonate
  参考文献：
  名称：

  A New, Efficient, and Catalyst-free Microwave-assisted Approach for Formation of O-tert-Butoxy Carbonates

  摘要：

  一种新的简单、高效、绿色且无催化剂的化学选择性方案用于各种结构多样的羟基化合物的O-叔丁氧基碳酰化，反应使用了（Boc）2O，并在微波辐射下进行。相应的O-叔丁氧基碳酸酯在较短的反应时间内以良好到优秀的产率获得，且没有任何副反应。

  DOI：

  10.1246/cl.140075

文献信息

• Chemoselective O-tert-butoxycarbonylation of phenols using 6,7-dimethoxyisoquinoline as a novel organocatalyst
  作者：Yukako Saito、Yuichi Yoshimura、Hiroki Takahata

  DOI：10.1016/j.tetlet.2010.10.114

  日期：2010.12

  The chemoselective O-tert-butoxycarbonylation of phenols using low levels (5-0.1 mol %) of 6,7-dimethoxyisoquinoline as a reusableorganocatalyst is described. (C) 2010 Elsevier Ltd. All rights reserved.
• Iridium-catalyzed C–H activation/borylation/oxidation for the preparation of bis-protected phloroglucinol derivatives
  作者：Laura J. Marshall、Karl M. Cable、Nigel P. Botting

  DOI：10.1016/j.tetlet.2010.03.049

  日期：2010.5

  The preparation of bis-protected phloroglucinol derivatives from a range of protected resorcinol substrates is presented. Functionalization was achieved via a two-step, one-pot iridium-catalyzed C-H activation/borylation/oxidation protocol. Our system gave high conversions to the arylboronic esters and good yields of the desired phenols following subsequent oxidation. A range of common protecting group categories was studied including alkyl, silyl, ether and ester. (C) 2010 Elsevier Ltd. All rights reserved.
• A New, Efficient, and Catalyst-free Microwave-assisted Approach for Formation of <i>O</i>-<i>tert</i>-Butoxy Carbonates
  作者：Hacène K’tir、Aïcha Amira、Malika Berredjem、Nour-Eddine Aouf

  DOI：10.1246/cl.140075

  日期：2014.6.5

  A new simple, efficient, greener, and catalyst-free chemoselective protocol for the O-tert-butoxycarbonylation of various structurally diverse hydroxy compounds was carried out with (Boc)2O under microwave radiation. The corresponding O-tert-butoxy carbonates were obtained in good to excellent yields in a short reaction time without any side reactions.

  一种新的简单、高效、绿色且无催化剂的化学选择性方案用于各种结构多样的羟基化合物的O-叔丁氧基碳酰化，反应使用了（Boc）2O，并在微波辐射下进行。相应的O-叔丁氧基碳酸酯在较短的反应时间内以良好到优秀的产率获得，且没有任何副反应。