[(4R)-(+)-4-(2-methoxy-2-oxoethyl)-5-oxo-1,3-dioxolan-4-yl]acetic acid | 199341-35-0

• 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: [(4R)-(+)-4-(2-methoxy-2-oxoethyl)-5-oxo-1,3-dioxolan-4-yl]acetic acid
• 英文别名: 2-[(4R)-4-(2-methoxy-2-oxoethyl)-5-oxo-1,3-dioxolan-4-yl]acetic acid
• CAS: 199341-35-0
• 化学式: C₈H₁₀O₇
• 分子量: 218.163
• InChiKey: LDPXQIFJGYIBKV-MRVPVSSYSA-N

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：

  [(4R)-(+)-4-(2-methoxy-2-oxoethyl)-5-oxo-1,3-dioxolan-4-yl]acetic acid 在 草酰氯 作用下， 以 乙醚 为溶剂， 反应 72.0h， 生成 [(R)-4-(3-Diazo-2-oxo-propyl)-5-oxo-[1,3]dioxolan-4-yl]-acetic acid methyl ester
  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
• 作为产物：
  描述：

  5-氧代-1,3-二氧戊环-4,4-二乙酸 在 N,N-二甲基苯胺 、 三氯氧磷 作用下， 以 氯仿 为溶剂， 生成 [(4R)-(+)-4-(2-methoxy-2-oxoethyl)-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

• Synthesis of the ester side chains of some potently antileukemic harringtonia alkaloids from chiral citrates
  作者：Rachael A. Ancliff、Andrew T. Russell、Adam J. Sanderson

  DOI：10.1039/b605339d

  日期：——

  The selective reduction of one of the three carboxyl groups of two chiral citric acid derivatives to the corresponding aldehydes, under Rosenmund conditions, are reported together with the application of these aldehydes to the syntheses of the ester side chains of some potently antileukemic Cephalotaxus alkaloids e.g. anhydroharringtonine.

  据报道，在Rosenmund条件下，将两种手性柠檬酸衍生物的三个羧基之一选择性还原为相应的醛，以及将这些醛应用于某些强抗白血病的头足类生物碱（如脱水harringtonine）的酯侧链的合成。 。
• Prokop; Milewska, Polish Journal of Chemistry, 2009, vol. 83, # 7, p. 1317 - 1322
  作者：Prokop、Milewska

  DOI：——

  日期：——
• 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.