ethyl β-(2-ethylene ketal-cyclohexyl)propionate | 33050-94-1

• 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: ethyl β-(2-ethylene ketal-cyclohexyl)propionate
• 英文别名: 3-(1,4-dioxa-spiro[4.5]dec-6-yl)-propionic acid ethyl ester；3-(1,4-Dioxa-spiro[4.5]dec-6-yl)-propionsaeure-aethylester；Ethyl 3-(1,4-dioxaspiro[4.5]decan-6-yl)propanoate
• CAS: 33050-94-1
• 化学式: C₁₃H₂₂O₄
• 分子量: 242.315
• InChiKey: LAIFVXUMDDCLFV-UHFFFAOYSA-N

物化性质

• 沸点：
  99-101 °C(Press: 0.15 Torr)
• 密度：
  1.0822 g/cm3(Temp: 24 °C)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl β-(2-ethylene ketal-cyclohexyl)propionate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以96%的产率得到3-(1,4-dioxaspiro[4,5]dec-6-yl)propan-1-ol
  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
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 对甲苯磺酸 、 乙二醇 、 苯 作用下， 生成 ethyl β-(2-ethylene ketal-cyclohexyl)propionate
  参考文献：
  名称：

  The Reaction of 2-Substituted Cyclohexanones with Organometallic Compounds

  摘要：

  DOI：

  10.1021/ja01530a018

文献信息

• Indium triflate: a mild Lewis acid catalyst for thioacetalization and transthioacetalization
  作者：Sengodagounder Muthusamy、Srinivasarao Arulananda Babu、Chidambaram Gunanathan

  DOI：10.1016/s0040-4020(02)00897-9

  日期：2002.9

  Protection of a variety of carbonyl compounds as thioacetals using indium triflate, a mild Lewis acid catalyst, was achieved at ambient temperature in very good yield. Transthioacetalization of oxyacetals into thioacetals was also achieved in an excellent yield. A mixture of carbonyl compound and its respective oxyacetal was also completely converted into thioacetal in the presence of indium triflate. (C) 2002 Elsevier Science Ltd. All rights reserved.
• A Broadly Applicable Mild Method for the Synthesis of <i>gem</i>-Diperoxides from Corresponding Ketones or 1,3-Dioxolanes
  作者：Yun Li、Hong-Dong Hao、Qi Zhang、Yikang Wu

  DOI：10.1021/ol900262t

  日期：2009.4.2

  Ketones or ketals were readily converted into the corresponding gem-dihydroperoxides in high yields by treatment with ethereal H2O2 at ambient temperature in the presence of 2-5 mol % of phosphomolybdic acid.
• Srivastava; Kumar; Singh, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2001, vol. 40, # 12, p. 1248 - 1250
  作者：Srivastava、Kumar、Singh

  DOI：——

  日期：——
• 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.
• The Reaction of 2-Substituted Cyclohexanones with Organometallic Compounds
  作者：S. M. McElvain、Rodney B. Clampitt

  DOI：10.1021/ja01530a018

  日期：1959.11