((S)-4-Methoxycarbonylmethyl-5-oxo-[1,3]dioxolan-4-yl)-acetic acid | 199341-50-9

• 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: ((S)-4-Methoxycarbonylmethyl-5-oxo-[1,3]dioxolan-4-yl)-acetic acid
• 英文别名: 2-[(4S)-4-(2-methoxy-2-oxoethyl)-5-oxo-1,3-dioxolan-4-yl]acetic acid
• CAS: 199341-50-9
• 化学式: C₈H₁₀O₇
• 分子量: 218.163
• InChiKey: LDPXQIFJGYIBKV-QMMMGPOBSA-N

物化性质

• 沸点：
  405.0±20.0 °C(Predicted)
• 密度：
  1.403±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  99.1
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ((S)-4-Methoxycarbonylmethyl-5-oxo-[1,3]dioxolan-4-yl)-acetic acid 在 sodium hydroxide 、 chymotripsin 、 phosphate buffer pH=7 、 sodium ethanolate 作用下， 反应 96.0h， 生成 1,5-diethyl 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：

  柠檬酸 在 N,N-二甲基苯胺 、 三氯氧磷 作用下， 以 氯仿 、 二甲基亚砜 为溶剂， 生成 ((S)-4-Methoxycarbonylmethyl-5-oxo-[1,3]dioxolan-4-yl)-acetic acid
  参考文献：
  名称：

  Resolution of a citric acid derivative: synthesis of (R)-(−)-homocitric acid-γ-lactone

  摘要：

  Both the (R) and (S) enantiomers of the citric acid derivative 1 have been obtained in greater than or equal to 90% ee via resolution of the racemate by fractional crystallisation of the (S) and (R)-alpha-methylbenzylamine salts respectively. The stereochemistry of (R)-1 has been assigned by its conversion to (R)-(-)-homocitric acid utilising an Arndt-Eistert homologation followed by acid catalysed deprotection. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00435-7

文献信息

• Resolution of a citric acid derivative: synthesis of (R)-(−)-homocitric acid-γ-lactone
  作者：Rachael A. Ancliff、Andrew T. Russell、Adam J. Sanderson

  DOI：10.1016/s0957-4166(97)00435-7

  日期：1997.10

  Both the (R) and (S) enantiomers of the citric acid derivative 1 have been obtained in greater than or equal to 90% ee via resolution of the racemate by fractional crystallisation of the (S) and (R)-alpha-methylbenzylamine salts respectively. The stereochemistry of (R)-1 has been assigned by its conversion to (R)-(-)-homocitric acid utilising an Arndt-Eistert homologation followed by acid catalysed deprotection. (C) 1997 Elsevier Science Ltd.
• 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.