methyl 3-(1,3-dioxolan-2-yl)-2-hydroxypropanoate | 329735-16-2

• 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 3-(1,3-dioxolan-2-yl)-2-hydroxypropanoate
• CAS: 329735-16-2
• 化学式: C₇H₁₂O₅
• 分子量: 176.169
• InChiKey: LJBFENLVPASYHD-UHFFFAOYSA-N

物化性质

• 沸点：
  266.9±20.0 °C(Predicted)
• 密度：
  1.234±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 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 3-(1,3-dioxolan-2-yl)-2-hydroxypropanoate 在 Ru-carbon 氢气 、 对甲苯磺酸 作用下， 以 水 、 异丙醇 为溶剂， 60.0 ℃ 、2.0 MPa 条件下， 反应 6.0h， 以100%的产率得到(±)-α-羟基-γ-丁内酯
  参考文献：
  名称：

  Synthesis of α-hydroxy-γ-butyrolactones from acrylates and 1,3-dioxolanes using N-hydroxyphthalimide (NHPI) as a key catalyst

  摘要：

  A new route to alpha-hydroxy-gamma-butyrolactones through three-component radical coupling of 1,3-dioxoranes, acrylates, and molecular oxygen using N-hydroxyphthalimide (NHPI) as a key catalyst has been developed. For example, the addition of 1,3dioxarane to methyl acrylate under dioxygen by NHPI followed by catalytic hydrogenation of the resulting adduct on Pd/C afforded alpha-hydroxy-gamma-butyrolactone in good yield. This method provides a facile approach to alpha-hydroxy-gamma-butyrolactones, which are difficult to synthesize by conventional methods. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.03.137
• 作为产物：
  描述：

  1,3-二氧戊环 、 丙烯酸甲酯（MA） 在 4,9-(benzene-1,2-diyl)-2,4-dihydroxy-3a,4,9,9a-tetrahydro-1H-benzo[f]isoindole-1,3(2H)-dione 、 氧气 、 cobalt(II) acetate 作用下， 20.0 ℃ 、101.33 kPa 条件下， 以56%的产率得到methyl 3-(1,3-dioxolan-2-yl)-2-hydroxypropanoate
  参考文献：
  名称：

  Anthrone-derived NHPI analogues as catalysts in reactions using oxygen as an oxidant

  摘要：

  已开发出一种对映选择性的合成龙脑衍生的NHPI类似物。其中一种类似物与钴盐结合，应用于催化苄基化合物和二醇的好氧氧化。还进行了使用催化剂的外消旋版本进行的探索性研究。还证明了用分子氧作为终端氧化剂，二氧六烷或醇对活化烯烃的自由基加成也可由NHPI类似物催化。

  DOI：

  10.1039/b812351a

文献信息

• N-Hydroxyphthalimide-catalyzed radical addition of 1,3-dioxolanes and molecular oxygen to alkenes under ambient conditions: a new route to β-oxycarbonyl compounds
  作者：Kazutaka Hirano、Takahiro Iwahama、Satoshi Sakaguchi、Yasutaka Ishii

  DOI：10.1039/b008418m

  日期：——

  A novel catalytic hydroxyacylation of alkenes using 1,3-dioxolanes and molecular oxygen has been developed, and the reaction of 2-methyl-1,3-dioxolane with methyl acrylate under dioxygen atmosphere in the presence of catalytic amounts of NHPI and Co(OAc)2 produced the corresponding adduct in 81% yield.

  已经开发了一种使用 1,3-二氧戊环和分子氧的烯烃催化羟基酰化反应，并在催化量的 NHPI 和 Co(OAc) 存在下，在双氧气氛下与丙烯酸甲酯反应。 )2 以 81% 的产率产生相应的加合物。
• Synthesis of α-hydroxy-γ-butyrolactones from acrylates and 1,3-dioxolanes using N-hydroxyphthalimide (NHPI) as a key catalyst
  作者：Takashi Kagayama、Satoshi Sakaguchi、Yasutaka Ishii

  DOI：10.1016/j.tetlet.2005.03.137

  日期：2005.5

  A new route to alpha-hydroxy-gamma-butyrolactones through three-component radical coupling of 1,3-dioxoranes, acrylates, and molecular oxygen using N-hydroxyphthalimide (NHPI) as a key catalyst has been developed. For example, the addition of 1,3dioxarane to methyl acrylate under dioxygen by NHPI followed by catalytic hydrogenation of the resulting adduct on Pd/C afforded alpha-hydroxy-gamma-butyrolactone in good yield. This method provides a facile approach to alpha-hydroxy-gamma-butyrolactones, which are difficult to synthesize by conventional methods. (c) 2005 Elsevier Ltd. All rights reserved.
• Anthrone-derived NHPI analogues as catalysts in reactions using oxygen as an oxidant
  作者：Juan Shen、Choon-Hong Tan

  DOI：10.1039/b812351a

  日期：——

  An enantioselective synthesis of anthrone-derived NHPI analogues has been developed. One of these analogues, in combination with Co salts, was employed to catalyse the aerobic oxidation of benzylic compounds and diols. Exploratory studies using a racemic version of the catalyst were also conducted. Radical addition of dioxolanes or alcohols to activated alkenes with molecular oxygen as the terminal oxidant was also shown to be catalysed with NHPI analogues.

  已开发出一种对映选择性的合成龙脑衍生的NHPI类似物。其中一种类似物与钴盐结合，应用于催化苄基化合物和二醇的好氧氧化。还进行了使用催化剂的外消旋版本进行的探索性研究。还证明了用分子氧作为终端氧化剂，二氧六烷或醇对活化烯烃的自由基加成也可由NHPI类似物催化。