acetic acid 2-acetoxy-3-benzyloxy-propyl ester | 151121-12-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油脂
• 英文名称: acetic acid 2-acetoxy-3-benzyloxy-propyl ester
• 英文别名: acetic acid 2-acetoxy-3-benzyloxypropyl ester；3-(benzyloxy)propane-1,2-diyl diacetate；3-benzyloxy-1,2-diacetoxypropane；1,2-Di-O-acetyl-3-O-benzylglycerin；2,3-Diacetyl-1-O-benzylglycerol；3-Benzyloxy-1,2-diacetyl-1,2-propanediol；(2-acetyloxy-3-phenylmethoxypropyl) acetate
• CAS: 151121-12-9
• 化学式: C₁₄H₁₈O₅
• 分子量: 266.294
• InChiKey: PZJWZGWBDMSONK-UHFFFAOYSA-N

物化性质

• 沸点：
  140-143 °C(Press: 0.15 Torr)
• 密度：
  1.133±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿、二氯甲烷

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  19
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  acetic acid 2-acetoxy-3-benzyloxy-propyl ester 生成 (2R)-1,2-diacetoxy-3-(benzyloxy)propane
  参考文献：
  名称：

  Lipase-catalyzed enantiomer selective hydrolysis of 1,2-diol diacetates

  摘要：

  Enantiomer selective hydrolysis of racemic 1,2-diol diacetates (rac-2a-h) was investigated by using the inexpensive commercial porcine pancreatic lipase. The hydrolysis proceeds with variable regioselectivity but with moderate to good enantioselectively yielding a mixture of isomeric monoacetates (3a-h and 4a-h) and unchanged diacetate enantiomers (2a-h). Evidence was found that both monoacetates (3a-h and 4a-h) are formed with the same sense of enantiomer selectivity.

  DOI：

  10.1016/s0957-4166(00)80071-3
• 作为产物：
  描述：

  3-苄氧基-1,2-丙二醇 、 溶剂黄146 以 水 为溶剂， 反应 1.0h， 以85%的产率得到acetic acid 2-acetoxy-3-benzyloxy-propyl ester
  参考文献：
  名称：

  Lipid-improving agent and composition containing lipid-improving agent

  摘要：

  一种含有甘油三酯的脂质改善剂，其中多不饱和脂肪酸与甘油三酯的2位结合。

  公开号：

  US20060217441A1

文献信息

• Aerobic Acetoxyhydroxylation of Alkenes Co-catalyzed by Organic Nitrite and Palladium
  作者：Xian-Min Chen、Xiao-Shan Ning、Yan-Biao Kang

  DOI：10.1021/acs.orglett.6b02743

  日期：2016.10.21

  An aerobic acetoxyhydroxylation of alkenes cooperatively catalyzed by organic nitrite and palladium at room temperature using clean and cheap air as the sole oxidant has been developed. Various vicinal diols, diacetoxyalkanes, and dihalogenoalkanes have been synthesized. The gram-scale synthesis has also been approached. Vicinal difluorination and dichlorolation products have also been achieved via

  已经开发了有机亚硝酸盐和钯在室温下使用清洁廉价的空气作为唯一氧化剂协同催化的烯烃的好氧乙酰氧基羟化反应。已经合成了各种邻二醇，二乙酰氧基烷烃和二卤代烷烃。也已经进行了克级合成。通过该反应也已经获得了邻二氟和二氯化产物。
• Aerobic Palladium‐Catalyzed Dioxygenation of Alkenes Enabled by Catalytic Nitrite
  作者：Zachary K. Wickens、Pablo E. Guzmán、Robert H. Grubbs

  DOI：10.1002/anie.201408650

  日期：2015.1.2

  Catalytic nitrite was found to enable carbon–oxygen bond‐forming reductive elimination from unstable alkyl palladium intermediates, providing dioxygenated products from alkenes. A variety of functional groups were tolerated, and high yields (up to 94 %) were observed with many substrates, also for a multigram‐scale reaction. Nitrogen dioxide, which could form from nitrite under the reaction conditions

  发现催化亚硝酸盐可从不稳定的烷基钯中间体中消除碳-氧键，从而从烯烃中提供双氧合产物。可以容忍各种官能团，而且对于许多克级反应，在许多底物上都可以观察到高收率（高达94％）。在反应条件下可能由亚硝酸盐形成的二氧化氮被证明是催化循环中的潜在中间体。此外，还通过18个O标记实验探测了还原消除事件，结果表明双官能化产物中的两个氧原子均源自一分子乙酸。
• Palladium-Catalyzed Olefin Dioxygenation
  作者：Yang Li、Datong Song、Vy M. Dong

  DOI：10.1021/ja711029u

  日期：2008.3.1

  A general method for the vicinal dioxygenation of olefins was developed using cationic Pd diphosphine complexes as the catalysts and Phl(OAC)(2) as the terminal oxidant. In comparison to known Pd-catalyzed vicinal oxidations, this method is suitable for a broad range of olefins in both inter- and intramolecular reactions. An (18)O-labeling experiment provides insight into the mechanism of this transformation which presumably involves Pd(II)/Pd(IV) intermediates.
• Sukhanov,V.A. et al., Journal of general chemistry of the USSR, 1977, vol. 47, p. 1943 - 1947
  作者：Sukhanov,V.A. et al.

  DOI：——

  日期：——
• BF₃·OEt₂-Promoted Diastereoselective Diacetoxylation of Alkenes by PhI(OAc)₂
  作者：Wenhe Zhong、Jun Yang、Xiangbao Meng、Zhongjun Li

  DOI：10.1021/jo201752y

  日期：2011.12.16

  Selective syn and anti diacetoxylations of alkenes have been achieved using a PhI(OAc)(2)/BF3 center dot OEt2 system in the presence and absence of water, respectively. A broad range of substrates including electron-deficient alkenes (such as alpha,beta-unsaturated esters) could be elaborated efficiently at room temperature with this methodology, furnishing the desired products in good to excellent yields and diastereoselectivity. In particular, a multigram-scale diastereoselective diacetoxylation of methyl cinnamate (5.00 g) was also accomplished in a few hours, maintaining the same efficiency as small-scale reaction. This novel methodology provides an alternative approach for the preparation of various 1,2-diols.