(E)-5-(2-Oxo-cyclohexyl)-pent-2-enoic acid ethyl ester | 353460-57-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (E)-5-(2-Oxo-cyclohexyl)-pent-2-enoic acid ethyl ester
• 英文别名: ethyl (E)-5-(2-oxocyclohexyl)pent-2-enoate
• CAS: 353460-57-8
• 化学式: C₁₃H₂₀O₃
• 分子量: 224.3
• InChiKey: FNZYHUMHZOIADU-UXBLZVDNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 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：

  (E)-5-(2-Oxo-cyclohexyl)-pent-2-enoic acid ethyl ester 在 urea hydrogen peroxide 、 mercury(II) diacetate 、 scandium tris(trifluoromethanesulfonate) 作用下， 以 二氯甲烷 为溶剂， 反应 40.0h， 生成
  参考文献：
  名称：

  青蒿素（青蒿素）的简化类似物

  摘要：

  通过简单的途径设计并合成了三种新的青蒿素的简化类似物，而无需依靠常用的光敏氧化。目标分子中的过氧键取自UHP，第一个过氧-碳键通过半交换反应形成，第二个通过分子内迈克尔加成反应或通过Hg（II）介导的闭环反应形成。所有这三种过氧化物均具有一个与全碳六元环稠合的七元过氧环，这是生成以碳为中心的取代乙基基团所需的结构基序。

  DOI：

  10.1016/j.tet.2007.08.018
• 作为产物：
  描述：

  3-(1,4-dioxaspiro[4,5]dec-6-yl)propan-1-ol 在 草酰氯 、 对甲苯磺酸 、 二甲基亚砜 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 48.0h， 生成 (E)-5-(2-Oxo-cyclohexyl)-pent-2-enoic acid ethyl ester
  参考文献：
  名称：

  Visible Light Initiated Photosensitized Electron Transfer Cyclizations of Aldehydes and Ketones to Tethered α,β-Unsaturated Esters:  Stereoselective Synthesis of Optically Pure C-Furanosides

  摘要：

  Photosensitized one-electron reductive activation of aldehydes/ketones tethered with activated olefins leads to efficient cyclization to give diastereoselective cycloalkanols in high yield. The activation is promoted by secondary and dark electron transfer from visible light (405 nm) initiated photosensitized electron transfer generated 9,10-dicyanoanthracene radical anion (DCA(.-)). The DCA(.-) is produced by electron transfer using either triphenylphosphine (Ph3P) as sacrificial electron donor (PS-A) or 1,5-dimethoxynaphthalene (DMN) as primary electron donor and ascorbic acid as sacrificial electron donor (PS-B), to light-absorbing DCA. The cyclization is suggested to involve ketyl radical intermediate. High trans diastereoselectivity is observed during the formation of cycloalkanols. This cyclization strategy is further extended for the stereoselective synthesis of optically pure C-furanoside (41), starting from naturally occuring L-tartaric acid. The stereochemistry of 41 is suggested based on the single-crystal X-ray diffraction data.

  DOI：

  10.1021/jo9702812

文献信息

• The First Tandem [2 + 2] Cycloaddition−Michael Reaction Using Ynolates:  Facile Construction of Substituted Carbocycles
  作者：Mitsuru Shindo、Kenji Matsumoto、Yusuke Sato、Kozo Shishido

  DOI：10.1021/ol0159928

  日期：2001.6.1

  [GRAPHICS]A tandem [2 + 2] cycloaddition-Michael reaction using ynolate anions followed by decarboxylation produced polysubstituted five-, six-, and seven-membered cycloalkenes.
• Visible Light Initiated Photosensitized Electron Transfer Cyclizations of Aldehydes and Ketones to Tethered α,β-Unsaturated Esters:  Stereoselective Synthesis of Optically Pure <i>C</i>-Furanosides
  作者：Ganesh Pandey、Saumen Hajra、Manas K. Ghorai、K. Ravi Kumar

  DOI：10.1021/jo9702812

  日期：1997.8.1

  Photosensitized one-electron reductive activation of aldehydes/ketones tethered with activated olefins leads to efficient cyclization to give diastereoselective cycloalkanols in high yield. The activation is promoted by secondary and dark electron transfer from visible light (405 nm) initiated photosensitized electron transfer generated 9,10-dicyanoanthracene radical anion (DCA(.-)). The DCA(.-) is produced by electron transfer using either triphenylphosphine (Ph3P) as sacrificial electron donor (PS-A) or 1,5-dimethoxynaphthalene (DMN) as primary electron donor and ascorbic acid as sacrificial electron donor (PS-B), to light-absorbing DCA. The cyclization is suggested to involve ketyl radical intermediate. High trans diastereoselectivity is observed during the formation of cycloalkanols. This cyclization strategy is further extended for the stereoselective synthesis of optically pure C-furanoside (41), starting from naturally occuring L-tartaric acid. The stereochemistry of 41 is suggested based on the single-crystal X-ray diffraction data.
• Simplified analogues of qinghaosu (artemisinin)
  作者：Qi Zhang、Yikang Wu

  DOI：10.1016/j.tet.2007.08.018

  日期：2007.10

  Three new simplified analogues of qinghaosu have been designed and synthesized through simple routes without recourse to the commonly employed photosensitized oxidation. The peroxy bonds in the target molecules were taken from UHP with the first peroxy–carbon bond formed through a hemiketal exchange reaction and the second by either an intramolecular Michael addition or a Hg(II)-mediated ring-closure

  通过简单的途径设计并合成了三种新的青蒿素的简化类似物，而无需依靠常用的光敏氧化。目标分子中的过氧键取自UHP，第一个过氧-碳键通过半交换反应形成，第二个通过分子内迈克尔加成反应或通过Hg（II）介导的闭环反应形成。所有这三种过氧化物均具有一个与全碳六元环稠合的七元过氧环，这是生成以碳为中心的取代乙基基团所需的结构基序。