methyl 3-(2-bromoethyl)-6-hydroxy-2,4-dimethylbenzoate | 623936-71-0

• 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: methyl 3-(2-bromoethyl)-6-hydroxy-2,4-dimethylbenzoate
• 英文别名: Benzoic acid, 3-(2-bromoethyl)-6-hydroxy-2,4-dimethyl-, methyl ester
• CAS: 623936-71-0
• 化学式: C₁₂H₁₅BrO₃
• 分子量: 287.153
• InChiKey: HUVJFYKXSQWRDU-UHFFFAOYSA-N

物化性质

• 熔点：
  87-88 °C
• 沸点：
  359.6±42.0 °C(Predicted)
• 密度：
  1.405±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 3-(2-bromoethyl)-6-hydroxy-2,4-dimethylbenzoate 在 四(三苯基膦)钯 吡啶 、 potassium phosphate 、 三溴化硼 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 22.25h， 生成 8-(2-bromoethyl)-7,9-dimethyl-6H-benzo[c]chromen-6-one
  参考文献：
  名称：

  1，3-双（甲硅烷基烯醇醚）与3-甲硅烷氧基-2-烯-1-酮的[3 + 3]环化反应合成二苯并[ b，d ]吡喃-6-酮

  摘要：

  通过用3-甲硅烷氧基-2-en-1-one或1,1-将1,3-双（甲硅烷基烯醇醚）正式[3 + 3]环化制备官能化的二苯并[ b，d ]吡喃-6-。二乙酰环丙烷得到官能化的水杨酸酯，相应三氟甲磺酸酯的Suzuki交叉偶联反应以及随后的BBr 3介导的内酯化。二苯并[ b，d ]吡喃-6-酮的第二种方法依赖于1，3-双（甲硅烷基烯醇醚）与1-（2-甲氧基苯基）-1-（三甲基甲硅烷氧基）烷的环化[3 + 3] -1-en-3-ones和随后的BBr 3介导的内酯化。

  DOI：

  10.1021/jo070608r
• 作为产物：
  描述：

  甲基8-羟基-4,8-二甲基-6-氧代螺[2.5]辛-4-烯-5-羧酸酯 在 溴化钛(IV) 作用下， 以 二氯甲烷 为溶剂， 以94%的产率得到methyl 3-(2-bromoethyl)-6-hydroxy-2,4-dimethylbenzoate
  参考文献：
  名称：

  Synthesis, reactions and structure–activity relationships of 1-hydroxyspiro[2.5]cyclooct-4-en-3-ones: Illudin analogs with in vitro cytotoxic activity

  摘要：

  1-Hydroxyspiro [2.5]cyclooet-4-en-3-ones-analogs of natural illudines-were prepared in good yields by cyclization of 1,3-dicarbonyl dianions or 1,3-bis-silyl enol ethers ('masked dianions') with 1,1-diacylcyclopropanes. Several spirocyclopropanes showed a significant antiproliferative activity against human leukemia HL60 cells in vitro. 1-Hydroxyspiro [2.5]cyclooct-4-en-3-ones represent highly reactive precursors of unstable spiro[5.2]cycloocta-4,7-dien-6-ones and reactions with a number of nucleophiles were studied. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.03.037

文献信息

• Domino “[3+3]-Cyclization-Homo-Michael” Reactions of 1,3-Bissilyl Enol Ethers with 1,1-Diacylcyclopropanes
  作者：Gopal Bose、Van Thi Hong Nguyen、Ehsan Ullah、Sunanda Lahiri、Helmar Görls、Peter Langer

  DOI：10.1021/jo0485278

  日期：2004.12.1

  The Lewis acid mediated domino " [3+3] -cyclization-homo-Michael" reaction of 1,3-bissilyl enol ethers with 1,1-diacylcyclopropanes allows an efficient one-pot synthesis of functionalized salicylates containing a halogenated side chain. A great variety of substitution patterns could be realized by variation of the starting materials and of the Lewis acid. The mechanism of the domino process was studied.
• Synthesis of dibenzo[b,d]pyran-6-ones based on a ‘[3+3] cyclization–Suzuki cross-coupling’ strategy
  作者：Van Thi Hong Nguyen、Peter Langer

  DOI：10.1016/j.tetlet.2004.12.030

  日期：2005.2

  Functionalized dibenzo[b,d]pyran-6-ones were prepared by sequential '[3+3] cyclization-Suzuki cross-coupling' reactions. (C) 2004 Elsevier Ltd. All rights reserved.
• [3+3] Cyclizations of 1,3-Bis(silyl enol ether)s with 1,1-Diacetylcyclopentane and 1,1-Diacetylcyclopropane
  作者：Peter Langer、Gopal Bose

  DOI：10.1002/anie.200351263

  日期：2003.9.5
• Synthesis of Dibenzo[<i>b</i>,<i>d</i>]pyran-6-ones Based on [3 + 3] Cyclizations of 1,3-Bis(silyl enol ethers) with 3-Silyloxy-2-en-1-ones
  作者：Ibrar Hussain、Van Thi Hong Nguyen、Mirza Arfan Yawer、Tuan Thanh Dang、Christine Fischer、Helmut Reinke、Peter Langer

  DOI：10.1021/jo070608r

  日期：2007.8.1

  were prepared by formal [3 + 3] cyclization of 1,3-bis(silyl enol ethers) with 3-silyloxy-2-en-1-ones or 1,1-diacetylcyclopropane to give functionalized salicylates, Suzuki cross-coupling reactions of the corresponding triflates, and subsequent BBr3-mediated lactonization. A second approach to dibenzo[b,d]pyran-6-ones relies on the [3 + 3] cyclization of 1,3-bis(silyl enol ethers) with 1-(2-methoxyphe

  通过用3-甲硅烷氧基-2-en-1-one或1,1-将1,3-双（甲硅烷基烯醇醚）正式[3 + 3]环化制备官能化的二苯并[ b，d ]吡喃-6-。二乙酰环丙烷得到官能化的水杨酸酯，相应三氟甲磺酸酯的Suzuki交叉偶联反应以及随后的BBr 3介导的内酯化。二苯并[ b，d ]吡喃-6-酮的第二种方法依赖于1，3-双（甲硅烷基烯醇醚）与1-（2-甲氧基苯基）-1-（三甲基甲硅烷氧基）烷的环化[3 + 3] -1-en-3-ones和随后的BBr 3介导的内酯化。
• Synthesis, reactions and structure–activity relationships of 1-hydroxyspiro[2.5]cyclooct-4-en-3-ones: Illudin analogs with in vitro cytotoxic activity
  作者：Gopal Bose、Karin Bracht、Patrick J. Bednarski、Michael Lalk、Peter Langer

  DOI：10.1016/j.bmc.2006.03.037

  日期：2006.7.15

  1-Hydroxyspiro [2.5]cyclooet-4-en-3-ones-analogs of natural illudines-were prepared in good yields by cyclization of 1,3-dicarbonyl dianions or 1,3-bis-silyl enol ethers ('masked dianions') with 1,1-diacylcyclopropanes. Several spirocyclopropanes showed a significant antiproliferative activity against human leukemia HL60 cells in vitro. 1-Hydroxyspiro [2.5]cyclooct-4-en-3-ones represent highly reactive precursors of unstable spiro[5.2]cycloocta-4,7-dien-6-ones and reactions with a number of nucleophiles were studied. (c) 2006 Elsevier Ltd. All rights reserved.