(2S,3S)-(-)-2,3-dimethoxybutane-1,4-diyl bis(ethyl malonate) | 496067-15-3

• 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: (2S,3S)-(-)-2,3-dimethoxybutane-1,4-diyl bis(ethyl malonate)
• 英文别名: 3-O-[(2S,3S)-4-(3-ethoxy-3-oxopropanoyl)oxy-2,3-dimethoxybutyl] 1-O-ethyl propanedioate
• CAS: 496067-15-3
• 化学式: C₁₆H₂₆O₁₀
• 分子量: 378.376
• InChiKey: FRGDZLWETOFZOB-RYUDHWBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  26
• 可旋转键数：
  17
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  124
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  足球烯 、 (2S,3S)-(-)-2,3-dimethoxybutane-1,4-diyl bis(ethyl malonate) 在 碘 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲苯 为溶剂， 以5%的产率得到C₇₆H₂₂O₁₀
  参考文献：
  名称：

  Absolute Stereochemistry of Chiral C 60 Fullerene Bis-Adducts

  摘要：

  To determine the absolute configuration of chiral fullerene bis-adducts, we have studied the double Bingel reaction of C-60 with chiral tether (2S,3S)-(-)-9 derived from (R,R)-(+)-tartaric acid, and have succeeded in isolating two possible chiral bis-adducts 10a (5%) and 10b (2%) in addition to the C-s-symmetrically added derivative 10c (40%). The CD spectra of chiral bis-adducts [CD(+)281]-10a and [CD(-)281]-10b show very intense Cotton effects, which are almost of mirror image, indicating that their chiral C-60 pi-electron systems are enantiomeric each other. The H-1 and C-13 NMR spectra of 10a and 10b indicate that they have C-2-symmetrical structures, and the vicinal coupling constants between two equivalent protons H-2 and H-2' were determined as 1.2 Hz for 10a and 1.8 Hz for 10b, respectively by the 13 C satellite band method. From the conformational analyses, the absolute configurations of these chiral C60 fullerene bis-adducts were unambiguously determined as [CD(+)281]-(S,S,C-f)-10a and [CD(-)281]-(S,S,(f)A)-10b, respectively.

  DOI：

  10.1080/10242430210704
• 作为产物：
  描述：

  (R,R)-2,3-dimethoxy-succinic acid dimethyl ester 在 吡啶 、 lithium aluminium tetrahydride 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 生成 (2S,3S)-(-)-2,3-dimethoxybutane-1,4-diyl bis(ethyl malonate)
  参考文献：
  名称：

  Absolute Stereochemistry of Chiral C 60 Fullerene Bis-Adducts

  摘要：

  To determine the absolute configuration of chiral fullerene bis-adducts, we have studied the double Bingel reaction of C-60 with chiral tether (2S,3S)-(-)-9 derived from (R,R)-(+)-tartaric acid, and have succeeded in isolating two possible chiral bis-adducts 10a (5%) and 10b (2%) in addition to the C-s-symmetrically added derivative 10c (40%). The CD spectra of chiral bis-adducts [CD(+)281]-10a and [CD(-)281]-10b show very intense Cotton effects, which are almost of mirror image, indicating that their chiral C-60 pi-electron systems are enantiomeric each other. The H-1 and C-13 NMR spectra of 10a and 10b indicate that they have C-2-symmetrical structures, and the vicinal coupling constants between two equivalent protons H-2 and H-2' were determined as 1.2 Hz for 10a and 1.8 Hz for 10b, respectively by the 13 C satellite band method. From the conformational analyses, the absolute configurations of these chiral C60 fullerene bis-adducts were unambiguously determined as [CD(+)281]-(S,S,C-f)-10a and [CD(-)281]-(S,S,(f)A)-10b, respectively.

  DOI：

  10.1080/10242430210704

文献信息

• Absolute Stereochemistry of Chiral C 60 Fullerene Bis-Adducts
  作者：Kazuhiro Yoshida、Shuichi Osawa、Kenji Monde、Masataka Watanabe、Nobuyuki Harada

  DOI：10.1080/10242430210704

  日期：2002.1

  To determine the absolute configuration of chiral fullerene bis-adducts, we have studied the double Bingel reaction of C-60 with chiral tether (2S,3S)-(-)-9 derived from (R,R)-(+)-tartaric acid, and have succeeded in isolating two possible chiral bis-adducts 10a (5%) and 10b (2%) in addition to the C-s-symmetrically added derivative 10c (40%). The CD spectra of chiral bis-adducts [CD(+)281]-10a and [CD(-)281]-10b show very intense Cotton effects, which are almost of mirror image, indicating that their chiral C-60 pi-electron systems are enantiomeric each other. The H-1 and C-13 NMR spectra of 10a and 10b indicate that they have C-2-symmetrical structures, and the vicinal coupling constants between two equivalent protons H-2 and H-2' were determined as 1.2 Hz for 10a and 1.8 Hz for 10b, respectively by the 13 C satellite band method. From the conformational analyses, the absolute configurations of these chiral C60 fullerene bis-adducts were unambiguously determined as [CD(+)281]-(S,S,C-f)-10a and [CD(-)281]-(S,S,(f)A)-10b, respectively.