ethyl 3-(2-chloroethyl)-6-hydroxy-2,4-dimethylbenzoate | 716381-27-0

• 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: ethyl 3-(2-chloroethyl)-6-hydroxy-2,4-dimethylbenzoate
• CAS: 716381-27-0
• 化学式: C₁₃H₁₇ClO₃
• 分子量: 256.729
• InChiKey: KTGUUPMJNAZIRQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 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：

  ethyl 3-(2-chloroethyl)-6-hydroxy-2,4-dimethylbenzoate 在 sodium acetate buffer 、 Pycnoporus cinnabarinus laccase EC 1.10.3.1 作用下， 以 甲醇 、 水 为溶剂， 以74%的产率得到diethyl 5,5'-bis(2-chloroethyl)-2,2'-dihydroxy-4,6,4',6'-tetramethylbiphenyl-3,3'-dicarboxylate
  参考文献：
  名称：

  漆酶催化的碳-碳键形成：水溶液中空气对水杨酸酯的氧化二聚作用

  摘要：

  研究了漆酶催化水杨酸酯的氧化二聚反应，这是漆酶催化的碳-碳键形成的罕见例子。该反应允许使用空气作为化学计量的氧化剂，并在水溶液中进行。研究了该方法的制备范围和机理，该方法在温和条件下提供了一种新的和方便的方法来获得官能化联芳基。

  DOI：

  10.1016/j.tet.2005.03.007
• 作为产物：
  描述：

  Ethyl 8-hydroxy-4,8-dimethyl-6-oxospiro[2.5]oct-4-ene-5-carboxylate 在 三氟化硼乙醚 、 四丁基氯化铵 作用下， 以 二氯甲烷 为溶剂， 以84%的产率得到ethyl 3-(2-chloroethyl)-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 and reactivity of 1-hydroxyspiro[2.5]cyclooct-4-en-3-ones
  作者：Gopal Bose、Peter Langer

  DOI：10.1016/j.tetlet.2004.03.134

  日期：2004.5

  The first 1-hydroxyspiro[2.5]cyclooct-4-en-3-ones were prepared by cyclization of free and masked 1,3-dicarbonyl dia-nions with 1,1-diacetylcyclopropane. 1-Hydroxyspiro[2.5]cyclooct-4-en-3-ones represent precursors of unstable spiro[5.2]cycloocta-4,7-dien-6-ones and reactions with a number of nucleophiles were studied. The reactions are enhanced by dynamic spiro-activation. (C) 2004 Elsevier Ltd. All rights reserved.
• Laccase-catalyzed carbon–carbon bond formation: oxidative dimerization of salicylic esters by air in aqueous solution
  作者：Sabine Ciecholewski、Elke Hammer、Katrin Manda、Gopal Bose、Van T.H. Nguyen、Peter Langer、Frieder Schauer

  DOI：10.1016/j.tet.2005.03.007

  日期：2005.5

  The laccase catalyzed oxidative dimerization of salicylic esters, a rare example of a laccase-catalyzed carbon–carbon bond formation, was studied. This reaction allows the use of air as stoichiometric oxidant and proceeds in aqueous solution. The preparative scope and the mechanism of the method, which provides a new and convenient access to functionalized biaryls under mild conditions, were investigated

  研究了漆酶催化水杨酸酯的氧化二聚反应，这是漆酶催化的碳-碳键形成的罕见例子。该反应允许使用空气作为化学计量的氧化剂，并在水溶液中进行。研究了该方法的制备范围和机理，该方法在温和条件下提供了一种新的和方便的方法来获得官能化联芳基。
• 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.