8-hydroxy-4,8-dimethyl-5-(phenylsulfonyl)spiro[2.5]oct-4-en-6-one | 1021444-99-4

• 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: 8-hydroxy-4,8-dimethyl-5-(phenylsulfonyl)spiro[2.5]oct-4-en-6-one
• 英文别名: 5-(Benzenesulfonyl)-8-hydroxy-4,8-dimethylspiro[2.5]oct-4-en-6-one；5-(benzenesulfonyl)-8-hydroxy-4,8-dimethylspiro[2.5]oct-4-en-6-one
• CAS: 1021444-99-4
• 化学式: C₁₆H₁₈O₄S
• 分子量: 306.383
• InChiKey: MHHHHGTYLMVDQH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  79.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  8-hydroxy-4,8-dimethyl-5-(phenylsulfonyl)spiro[2.5]oct-4-en-6-one 在 三氟化硼乙醚 、 四丁基氯化铵 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以80%的产率得到4-(2-chloroethyl)-3,5-dimethyl-2-(phenylsulfonyl)phenol
  参考文献：
  名称：

  Synthesis and reactions of functionalized spirocyclopropanes by cyclization of dilithiated β-ketosulfones, α-cyanoacetone and diethyl 2-oxopropylphosphonate with 1,1-diacetylcyclopropane

  摘要：

  The cyclization of beta-ketosulfone, beta-ketonitrile and beta-ketophosphonate dianions with 1,1-diacetylcyclopropane afforded 1-hydroxyspiro[5.2]-cyclooct-4-en-3-ones, which were transformed, by reaction with tetrabutylammonium halides, into functionalized phenols containing a remote halide function. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.01.066
• 作为产物：
  描述：

  1,1-乙酰基环丙烷 、 苯磺酰丙酮 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 15.0h， 以30%的产率得到8-hydroxy-4,8-dimethyl-5-(phenylsulfonyl)spiro[2.5]oct-4-en-6-one
  参考文献：
  名称：

  Synthesis and reactions of functionalized spirocyclopropanes by cyclization of dilithiated β-ketosulfones, α-cyanoacetone and diethyl 2-oxopropylphosphonate with 1,1-diacetylcyclopropane

  摘要：

  The cyclization of beta-ketosulfone, beta-ketonitrile and beta-ketophosphonate dianions with 1,1-diacetylcyclopropane afforded 1-hydroxyspiro[5.2]-cyclooct-4-en-3-ones, which were transformed, by reaction with tetrabutylammonium halides, into functionalized phenols containing a remote halide function. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.01.066

文献信息

• Synthesis and reactions of functionalized spirocyclopropanes by cyclization of dilithiated β-ketosulfones, α-cyanoacetone and diethyl 2-oxopropylphosphonate with 1,1-diacetylcyclopropane
  作者：Nasir Rasool、Muhammad A. Rashid、Helmut Reinke、Christine Fischer、Peter Langer

  DOI：10.1016/j.tet.2008.01.066

  日期：2008.3

  The cyclization of beta-ketosulfone, beta-ketonitrile and beta-ketophosphonate dianions with 1,1-diacetylcyclopropane afforded 1-hydroxyspiro[5.2]-cyclooct-4-en-3-ones, which were transformed, by reaction with tetrabutylammonium halides, into functionalized phenols containing a remote halide function. (c) 2008 Elsevier Ltd. All rights reserved.