5,5-Bis-methoxycarbonylmethyl-[1,3]dioxolan-4-on | 77862-72-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 5,5-Bis-methoxycarbonylmethyl-[1,3]dioxolan-4-on
• 英文别名: (5-oxo-[1,3]dioxolane-4,4-diyl)-bis-acetic acid dimethyl ester；5,5-bis-methoxycarbonylmethyl-[1,3]dioxolan-4-one；(5-Oxo-[1,3]dioxolan-4,4-diyl)-di-essigsaeure-dimethylester；1,3-Dioxolane-4,4-diacetic acid, 5-oxo-, dimethyl ester；methyl 2-[4-(2-methoxy-2-oxoethyl)-5-oxo-1,3-dioxolan-4-yl]acetate
• CAS: 77862-72-7
• 化学式: C₉H₁₂O₇
• 分子量: 232.19
• InChiKey: LUNFBLOSJFIJHC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  88.1
• 氢给体数：
  0
• 氢受体数：
  7

安全信息

• 海关编码：
  2932999099

反应信息

• 作为反应物：
  描述：

  5,5-Bis-methoxycarbonylmethyl-[1,3]dioxolan-4-on 在 sodium hydroxide 、 pig liver esterase 、 phosphate buffer pH=7 、 三乙胺 作用下， 反应 2.0h， 生成 (R)-Dimethyl citrate
  参考文献：
  名称：

  Regio- and enantioselectivity of the enzyme-catalyzed hydrolysis of citric acid derivatives

  摘要：

  The hydrolysis of triethyl citrate in the presence of three serine proteases (chymotrypsin, subtilisin in BPN', Is subtilisin carlsberg) is highly regioselective and gives the symmetric diester. Several lipases and proteases have the complementary regioselectivity and give the chiral diester. Pig liver esterase, Aspergillus niger lipase and Candida antarctica lipase give the chiral (R)-diester with good regio- and enantioselectivity. The stereoselective hydrolysis of the meso citric derivatives 7a,b in the presence of Candida antarctica lipase gives the corresponding (R)-monoester. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00448-0
• 作为产物：
  描述：

  甲醇 、 5-氧代-1,3-二氧戊环-4,4-二乙酸 在 甲醇 、 1,1-二甲氧基丙烷 、 DOWEX 50WX₄ 作用下， 反应 24.0h， 以86%的产率得到5,5-Bis-methoxycarbonylmethyl-[1,3]dioxolan-4-on
  参考文献：
  名称：

  Regio- and enantioselectivity of the enzyme-catalyzed hydrolysis of citric acid derivatives

  摘要：

  The hydrolysis of triethyl citrate in the presence of three serine proteases (chymotrypsin, subtilisin in BPN', Is subtilisin carlsberg) is highly regioselective and gives the symmetric diester. Several lipases and proteases have the complementary regioselectivity and give the chiral diester. Pig liver esterase, Aspergillus niger lipase and Candida antarctica lipase give the chiral (R)-diester with good regio- and enantioselectivity. The stereoselective hydrolysis of the meso citric derivatives 7a,b in the presence of Candida antarctica lipase gives the corresponding (R)-monoester. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00448-0

文献信息

• Nau; Brown; Bailey, Journal of the American Chemical Society, 1925, vol. 47, p. 2602
  作者：Nau、Brown、Bailey

  DOI：——

  日期：——
• Casini et al., Annali di Chimica, 1959, vol. 49, p. 499,504
  作者：Casini et al.

  DOI：——

  日期：——
• Regio- and enantioselectivity of the enzyme-catalyzed hydrolysis of citric acid derivatives
  作者：Robert Chênevert、Béatrice Tchédam Ngatcha、Yannick Stéphane Rose、Daniel Goupil

  DOI：10.1016/s0957-4166(98)00448-0

  日期：1998.12

  The hydrolysis of triethyl citrate in the presence of three serine proteases (chymotrypsin, subtilisin in BPN', Is subtilisin carlsberg) is highly regioselective and gives the symmetric diester. Several lipases and proteases have the complementary regioselectivity and give the chiral diester. Pig liver esterase, Aspergillus niger lipase and Candida antarctica lipase give the chiral (R)-diester with good regio- and enantioselectivity. The stereoselective hydrolysis of the meso citric derivatives 7a,b in the presence of Candida antarctica lipase gives the corresponding (R)-monoester. (C) 1998 Elsevier Science Ltd. All rights reserved.