(2-iodo-3-oxocyclohex-1-en-1-yl)methyl pivalate | 181041-43-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2-iodo-3-oxocyclohex-1-en-1-yl)methyl pivalate
• 英文别名: (2-Iodo-3-oxocyclohexen-1-yl)methyl 2,2-dimethylpropanoate
• CAS: 181041-43-0
• 化学式: C₁₂H₁₇IO₃
• 分子量: 336.17
• InChiKey: SQBCLQDVQCEFJV-UHFFFAOYSA-N

物化性质

• 沸点：
  369.1±42.0 °C(Predicted)
• 密度：
  1.51±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2-iodo-3-oxocyclohex-1-en-1-yl)methyl pivalate 在 甲醇 、 potassium carbonate 作用下， 反应 5.0h， 以55%的产率得到3-(hydroxymethyl)-2-iodocyclohex-2-en-1-one
  参考文献：
  名称：

  Synthesis of an epoxyquinol analog: efficient methodology for the insertion of side chains into cyclohexenone cores

  摘要：

  A novel epoxyquinol analog was prepared by molecular simplification of monomeric and dimeric scaffolds. A feasible methodology for the insertion of side chains into cyclohexenone skeleton was developed. Insertion of the hydroxymethyl side chain was achieved through alpha-sulfonylcarbanion chemistry. The alkenyl chain was inserted through palladium cross-coupling strategy. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.10.138
• 作为产物：
  描述：

  7-tosyl-1,4-dioxaspiro[4.5]decane 在 吡啶 、 正丁基锂 、 2,6-二叔丁基-4-甲基苯酚 、 氢氟酸 、 碘 、 [双(三氟乙酰氧基)碘]苯 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 34.33h， 生成 (2-iodo-3-oxocyclohex-1-en-1-yl)methyl pivalate
  参考文献：
  名称：

  Escobarines 功能化环 C 的合成

  摘要：

  开发了一种合成策略，用于从环己烯酮制备 α-乙炔基-α,β-环氧-β-甲酰基-和 α-乙炔基-α,β-环氧-β-（羟甲基）环己酮，作为拟议合成中的模型研究escobarines。这种高度官能化的环存在于抗结核 cassane 型二萜 escobarines A 和 B 中。 β-羟甲基的引入是通过使用磺酰基的阴离子和多聚甲醛的亲电攻击逆转烯酮的化学反应性来进行的. β-（羟甲基）环己烯酮的进一步官能化提供了所需的化合物。

  DOI：

  10.1002/ejoc.201501312

文献信息

• Palladium-catalyzed cross-coupling reactions of arylmetal compounds with β-substituted α-iodoenones and a cyclohexyl triflate
  作者：Folkert Boße、Ashok Rao Tunoori、AndréJ. Niestroj、Oliver Gronwald、Martin E. Maier

  DOI：10.1016/0040-4020(96)00489-9

  日期：1996.7

  Electron-rich arylstannanes were found to couple with α-iodoenones in the presence of Pd2(dba)3·CHCl3, a weak-coordinating ligand [AsPh3 or Pd(o-tol)3] and CuI (0.75-1.0 equiv) to give sterically hindered α-arylcyclohexenones 15–20. In addition, compounds 19, 22 and 23 were prepared by Suzuki coupling reactions of the cyclohexyl derivatives 7c,f and 11, respectively, with the arylboronic acid 21.

  发现在存在弱配位配体[AsPh 3或Pd（邻甲苯基）3 ]和CuI（0.75-1.0当量）的Pd 2（dba）3 ·CHCl 3的存在下，富电子芳基斯坦酮与α-碘代烯偶联。）可得到空间受阻的α-芳基环己烯酮15–20。另外，分别通过环己基衍生物7c，f和11与芳基硼酸21的Suzuki偶联反应制备化合物19、22和23。
• Cross-coupling approach towards dynemicin analogs without the nitrogen
  作者：Folkert Boße、Ashok Rao Tunoori、Martin E. Maier

  DOI：10.1016/s0040-4020(97)00616-9

  日期：1997.7

  Utilizing a cross-coupling reaction between the arylstannane 5 and the iodoenone 7, the arylcyclohexenone 8 was prepared. This compound was then transformed into the enediyne aldehydes 16a,b. Treatment of 16a with cat. amounts of TBAF gave rise to the macrocyclic dynemicin analog 17a. This was converted to the phenolic enediyne 18. (C) 1997 Elsevier Science Ltd.
• Synthesis of Functionalized Ring C of Escobarines
  作者：Harim Lechuga-Eduardo、Moises Romero-Ortega、Horacio F. Olivo

  DOI：10.1002/ejoc.201501312

  日期：2016.1

  A synthetic strategy was developed for the preparation of α-ethynyl-α,β-epoxy-β-formyl- and α-ethynyl-α,β-epoxy-β-(hydroxymethyl)cyclohexanone from cyclohexenone as a model study in a proposed synthesis of escobarines. This highly functionalized ring is found in the anti-TB cassane-type diterpenes escobarines A and B. Introduction of the β-hydroxymethyl group was carried out by reversing the chemical

  开发了一种合成策略，用于从环己烯酮制备 α-乙炔基-α,β-环氧-β-甲酰基-和 α-乙炔基-α,β-环氧-β-（羟甲基）环己酮，作为拟议合成中的模型研究escobarines。这种高度官能化的环存在于抗结核 cassane 型二萜 escobarines A 和 B 中。 β-羟甲基的引入是通过使用磺酰基的阴离子和多聚甲醛的亲电攻击逆转烯酮的化学反应性来进行的. β-（羟甲基）环己烯酮的进一步官能化提供了所需的化合物。
• Synthesis of an epoxyquinol analog: efficient methodology for the insertion of side chains into cyclohexenone cores
  作者：Viviana Heguaburu、Valeria Schapiro、Enrique Pandolfi

  DOI：10.1016/j.tetlet.2010.10.138

  日期：2010.12

  A novel epoxyquinol analog was prepared by molecular simplification of monomeric and dimeric scaffolds. A feasible methodology for the insertion of side chains into cyclohexenone skeleton was developed. Insertion of the hydroxymethyl side chain was achieved through alpha-sulfonylcarbanion chemistry. The alkenyl chain was inserted through palladium cross-coupling strategy. (C) 2010 Elsevier Ltd. All rights reserved.