ethyl ether d-malic acid diethyl ester | 17596-10-0

• 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: ethyl ether d-malic acid diethyl ester
• 英文别名: rechtsdrehender Aethoxy-bernsteinsaeure-diaethylester；Aethylaether-d-aepfelsaeure-diaethylester；diethyl (2R)-2-ethoxybutanedioate
• CAS: 17596-10-0
• 化学式: C₁₀H₁₈O₅
• 分子量: 218.25
• InChiKey: SYCKGYYABBRUOZ-MRVPVSSYSA-N

物化性质

• 沸点：
  92-93 °C(Press: 2 Torr)
• 密度：
  1.052±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：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 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：

  ethyl ether d-malic acid diethyl ester 在 palladium on activated charcoal 吡啶 、 lithium aluminium tetrahydride 、 sodium azide 、 氢气 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 100.0 ℃ 、7.3 MPa 条件下， 反应 9.5h， 生成 (R)-2-ethoxy-1,4-diaminobutane
  参考文献：
  名称：

  Synthesis and in vitro cytotoxicity of novel hydrophilic chiral 2-alkoxy-1,4-butanediamine platinum (II) complexes

  摘要：

  Twenty-six new hydrophilic chiral 2-alkoxy-1,4-butanediamine platinum (II) complexes having a seven-membered ring structure between a bidentate carrier ligand and a platinum atom have been synthesized and most of them were evaluated for their in vitro cytotoxicity toward A549 human non-small cell lung carcinoma and HCT-116 human colon cancer cell lines. The cytotoxicities of platinum complexes are related to the nature of the carrier ligand and leaving group. Complex 5'b, viz. cis-dichloro[(2R)ethoxy-1,4-butanediamine] platinum (11), exhibits the greatest potency among those 21 tested platinum complexes in both cell lines. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.08.025
• 作为产物：
  描述：

  D-(+)-苹果酸二乙酯 、 碘乙烷 在 silver(l) oxide 作用下， 反应 6.0h， 以83%的产率得到ethyl ether d-malic acid diethyl ester
  参考文献：
  名称：

  Synthesis and in vitro cytotoxicity of novel hydrophilic chiral 2-alkoxy-1,4-butanediamine platinum (II) complexes

  摘要：

  Twenty-six new hydrophilic chiral 2-alkoxy-1,4-butanediamine platinum (II) complexes having a seven-membered ring structure between a bidentate carrier ligand and a platinum atom have been synthesized and most of them were evaluated for their in vitro cytotoxicity toward A549 human non-small cell lung carcinoma and HCT-116 human colon cancer cell lines. The cytotoxicities of platinum complexes are related to the nature of the carrier ligand and leaving group. Complex 5'b, viz. cis-dichloro[(2R)ethoxy-1,4-butanediamine] platinum (11), exhibits the greatest potency among those 21 tested platinum complexes in both cell lines. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.08.025

文献信息

• Purdie; Williamson, Journal of the Chemical Society, 1895, vol. 67, p. 970
  作者：Purdie、Williamson

  DOI：——

  日期：——
• Enantio- and regioselective monohydrolysis of diethyl 2-ethoxysuccinate
  作者：Beat Wirz、Paul Spurr

  DOI：10.1016/0957-4166(95)00056-u

  日期：1995.3

  A procedure for the synthesis of (S)-ethyl 2-ethoxy-4-succinate 2 in 95% e.e. using a lipase from Candida rugosa was developed. The enzymatic reaction was highly selective for the secondary ester group and provided the desired (S)-monoacid in 40% yield. The unchanged (R)-diester was readily racemized and recycled.
• Synthesis and in vitro cytotoxicity of novel hydrophilic chiral 2-alkoxy-1,4-butanediamine platinum (II) complexes
  作者：Haibin Zhu、Kai Cui、Lianhong Wang、Shaohua Gou

  DOI：10.1016/j.bmcl.2005.08.025

  日期：2005.11

  Twenty-six new hydrophilic chiral 2-alkoxy-1,4-butanediamine platinum (II) complexes having a seven-membered ring structure between a bidentate carrier ligand and a platinum atom have been synthesized and most of them were evaluated for their in vitro cytotoxicity toward A549 human non-small cell lung carcinoma and HCT-116 human colon cancer cell lines. The cytotoxicities of platinum complexes are related to the nature of the carrier ligand and leaving group. Complex 5'b, viz. cis-dichloro[(2R)ethoxy-1,4-butanediamine] platinum (11), exhibits the greatest potency among those 21 tested platinum complexes in both cell lines. (c) 2005 Elsevier Ltd. All rights reserved.