ethyl 2-[hydroxy(6-methoxy-2,2-dimethyl-(3aR,5R,6S,6aR)-perhydrofuro[2,3-d][1,3]dioxol-5-yl)methyl]acrylate | 867266-20-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: ethyl 2-[hydroxy(6-methoxy-2,2-dimethyl-(3aR,5R,6S,6aR)-perhydrofuro[2,3-d][1,3]dioxol-5-yl)methyl]acrylate
• 英文别名: ethyl 2-[[(3aR,5R,6S,6aR)-6-methoxy-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-hydroxymethyl]prop-2-enoate
• CAS: 867266-20-4
• 化学式: C₁₄H₂₂O₇
• 分子量: 302.324
• InChiKey: VQFYCXWPMPJVEN-NOJOXAQASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  83.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ethyl 2-[hydroxy(6-methoxy-2,2-dimethyl-(3aR,5R,6S,6aR)-perhydrofuro[2,3-d][1,3]dioxol-5-yl)methyl]acrylate 在 lithium aluminium tetrahydride 、 三氯化铝 作用下， 以 乙醚 为溶剂， 反应 2.0h， 以68%的产率得到1-[6-methoxy-2,2-dimethyl-(3aR,5R,6S,6aR)-perhydrofuro[2,3-d][1,3]dioxol-5-yl]-2-methylene-1,3-propanediol
  参考文献：
  名称：

  Steric determinants in diastereocontrol during Baylis–Hillman reaction of sugar-derived aldehydes

  摘要：

  Diastereoselective Baylis-Hillman reaction using different sugar-derived aldehydes with various activated olefins afforded chiral multifunctional adducts in good yields. Steric factors that dictate and determine the diastereoselection will be discussed. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.06.026
• 作为产物：
  描述：

  1,2-O-异亚丙基-3-O-甲基-Alpha-D-木五二呋喃醛糖-(1,4) 、 丙烯酸乙酯 在 三乙烯二胺 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 15.0h， 以74%的产率得到ethyl 2-[hydroxy(6-methoxy-2,2-dimethyl-(3aR,5R,6S,6aR)-perhydrofuro[2,3-d][1,3]dioxol-5-yl)methyl]acrylate
  参考文献：
  名称：

  Steric determinants in diastereocontrol during Baylis–Hillman reaction of sugar-derived aldehydes

  摘要：

  Diastereoselective Baylis-Hillman reaction using different sugar-derived aldehydes with various activated olefins afforded chiral multifunctional adducts in good yields. Steric factors that dictate and determine the diastereoselection will be discussed. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.06.026

文献信息

• Sulpholane––A new solvent for the Baylis–Hillman reaction
  作者：Palakodety Radha Krishna、A. Manjuvani、V. Kannan、G.V.M. Sharma

  DOI：10.1016/j.tetlet.2003.11.137

  日期：2004.2

  Sulpholane, a commercially available solvent, is used for the first time as a new solvent for the Baylis-Hillman reaction tinder ambient conditions; a wide variety of olefins as well as aldehydes participate very efficiently resulting in good to excellent yields of products. Acrylamide also underwent the Baylis-Hillman reaction with 4-nitrobenzaldehyde under these reaction conditions. (C) 2003 Elsevier Ltd. All rights reserved.
• Krishna, Palakodety Radha; Kannan, Vembaiyan; Sharma, Gangavaram V. M., Synlett, 2003, # 6, p. 888 - 890
  作者：Krishna, Palakodety Radha、Kannan, Vembaiyan、Sharma, Gangavaram V. M.、Rao, Mallem H. V. Ramana

  DOI：——

  日期：——