[6-(Acetyloxymethyl)cyclohexa-1,5-dien-1-yl]methyl acetate | 333310-33-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: [6-(Acetyloxymethyl)cyclohexa-1,5-dien-1-yl]methyl acetate
• CAS: 333310-33-1
• 化学式: C₁₂H₁₆O₄
• 分子量: 224.257
• InChiKey: XYPWMWZGNQLJTB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-羟基氨基甲酸叔丁酯 、 [6-(Acetyloxymethyl)cyclohexa-1,5-dien-1-yl]methyl acetate 在 tetrapropylammonium periodate 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以75%的产率得到
  参考文献：
  名称：

  Functional Group Scope in the Methylene-Free, Tandem Enyne Metathesis

  摘要：

  The methylene-free ring synthesis of 1,3-cyclohexadienes has been expanded to include a diverse set of functional group-rich terminal and internal alkynes.

  DOI：

  10.1021/ol060727d
• 作为产物：
  描述：

  1,5-cis,cis-cyclooctadiene 、 1,4-二乙酰氧基-2-丁炔 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以63%的产率得到[6-(Acetyloxymethyl)cyclohexa-1,5-dien-1-yl]methyl acetate
  参考文献：
  名称：

  Functional Group Scope in the Methylene-Free, Tandem Enyne Metathesis

  摘要：

  The methylene-free ring synthesis of 1,3-cyclohexadienes has been expanded to include a diverse set of functional group-rich terminal and internal alkynes.

  DOI：

  10.1021/ol060727d

文献信息

• Tandem dienyne cross-metathesis/ring-closing metathesis
  作者：Jason A Smulik、Steven T Diver

  DOI：10.1016/s0040-4039(00)01922-5

  日期：2001.1

  Tandem enyne cross-metathesis/ring-closing metathesis between terminal alkynes and 1,5-hexadiene has been demonstrated using the 1,3-dimesityl-4,5-dihydroimidazol-2-ylidene-substituted ruthenium benzylidene complex. Synthesis of 2-substituted 1,3-cyclohexadienes using this one step tandem reaction is reported. In addition, metathesis products were subjected to [4+2] cycloaddition with N-methylmaleimide

  末端炔烃和1,5-己二烯之间的串联烯炔交叉复分解/闭环易位反应已使用1,3-二甲磺酰基-4,5-二氢咪唑-2-亚烷基取代的钌亚苄基络合物进行了证明。报道了使用这一一步串联反应合成2-取代的1，3-环己二烯。此外，在一个合成步骤中，将易位产物与N-甲基马来酰亚胺进行[4 + 2]环加成反应，得到相应的环加合物。
• Synthesis of 1,3-cyclohexadienes by tandem diene–alkyne metathesis: improved procedure
  作者：Mark D. Middleton、Steven T. Diver

  DOI：10.1016/j.tetlet.2005.04.017

  日期：2005.6

  A practical synthesis of 2-substituted 1,3-cyclohexadienes by the cross enyne metathesis between alkynes and 1,5-hexadiene is reported. The isolation of the 1,3-cyclohexadienes has been hampered by the formation of an inseparable triene by-product. The use of a second consecutive cross alkene metathesis to give water-soluble products allowed removal of this by-product. Using this one-pot procedure, a synthesis of cyclohexadienes from simple starting materials was developed. The procedure was used in a three-step synthesis of a functionalized tetrahydroquinoline using Pd(II)-catalyzed chloroacetoxyiation (Backvall reaction) for cyclohexadiene functionalization. (c) 2005 Elsevier Ltd. All rights reserved.