methyl (Z)-3-[(4R,5S)-5-hydroxymethyl-2,2-dimethyl-1,3-dioxolan-4-yl]-2-propenoate | 891193-73-0

• 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: methyl (Z)-3-[(4R,5S)-5-hydroxymethyl-2,2-dimethyl-1,3-dioxolan-4-yl]-2-propenoate
• 英文别名: methyl (Z)-3-[(4R,5S)-5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]prop-2-enoate
• CAS: 891193-73-0
• 化学式: C₁₀H₁₆O₅
• 分子量: 216.234
• InChiKey: ZGSWVZMGMHNJDN-YKCGFPGDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl (Z)-3-[(4R,5S)-5-hydroxymethyl-2,2-dimethyl-1,3-dioxolan-4-yl]-2-propenoate 在 重铬酸吡啶 、 3 A molecular sieve 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以74%的产率得到methyl (Z)-3-[(4R,5R)-5-formyl-2,2-dimethyl-1,3-dioxolan-4-yl]-2-propenoate
  参考文献：
  名称：

  Synthesis of enantiomerically pure hydroxylated pyrroline N-oxides from d-ribose

  摘要：

  A convenient way to obtain enantiomerically pure hydroxylated pyrroline N-oxides is reported. The key step is the formation of omega-oxo criciates from (D)-ribose and a subsequent 1,3-azaprotio cyclotransfer reaction of the resulting oximino alkenoate derivatives. The stereochemistry of the nitrones obtained is discussed in relation to that of the starting compounds. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.02.006
• 作为产物：
  描述：

  D-O²,O³-isopropylidene-ribitol 在 sodium periodate 、 苯甲酸 作用下， 以 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 18.0h， 生成 methyl (Z)-3-[(4R,5S)-5-hydroxymethyl-2,2-dimethyl-1,3-dioxolan-4-yl]-2-propenoate
  参考文献：
  名称：

  Synthesis of enantiomerically pure hydroxylated pyrroline N-oxides from d-ribose

  摘要：

  A convenient way to obtain enantiomerically pure hydroxylated pyrroline N-oxides is reported. The key step is the formation of omega-oxo criciates from (D)-ribose and a subsequent 1,3-azaprotio cyclotransfer reaction of the resulting oximino alkenoate derivatives. The stereochemistry of the nitrones obtained is discussed in relation to that of the starting compounds. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.02.006

文献信息

• Synthesis of S-functionalized thioesters using thioaroylate ions derived from carboxylic acids and tetrathiomolybdate via acyloxyphosphonium intermediates
  作者：Purushothaman Gopinath、Chanda Debasree、Ravindran Sasitha Vidyarini、Srinivasan Chandrasekaran

  DOI：10.1016/j.tet.2010.06.028

  日期：2010.8

  Thioaroylate ions generated in situ from acyloxyphosphonium salts and tetrathiomolybdate upon Michael addition or ring opening of three membered systems led to a facile synthesis of S-functionalized thioesters. While the ring opening of aziridines gave very good yield of the products, Michael addition and epoxide ring opening gave moderate yields.

  在三元体系的迈克尔加成或开环后，由酰氧基phosph盐和四硫代钼酸盐原位产生的硫代芳族酸酯离子导致了S-官能化硫酯的简便合成。尽管氮丙啶的开环给出了非常好的产物收率，但是迈克尔加成和环氧化物的开环给出了中等收率。
• Synthesis of enantiomerically pure hydroxylated pyrroline N-oxides from d-ribose
  作者：Nikolaos G. Argyropoulos、Theodoros D. Panagiotidis、John K. Gallos

  DOI：10.1016/j.tetasy.2006.02.006

  日期：2006.3

  A convenient way to obtain enantiomerically pure hydroxylated pyrroline N-oxides is reported. The key step is the formation of omega-oxo criciates from (D)-ribose and a subsequent 1,3-azaprotio cyclotransfer reaction of the resulting oximino alkenoate derivatives. The stereochemistry of the nitrones obtained is discussed in relation to that of the starting compounds. (c) 2006 Elsevier Ltd. All rights reserved.