O,O'-sec-butylidene-L_g-tartaric acid dimethyl ester | 68572-77-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: O,O'-sec-butylidene-L_g-tartaric acid dimethyl ester
• 英文别名: O,O'-sec-Butyliden-L_g-weinsaeure-dimethylester；dimethyl (4R,5R)-2-ethyl-2-methyl-1,3-dioxolane-4,5-dicarboxylate
• CAS: 68572-77-0
• 化学式: C₁₀H₁₆O₆
• 分子量: 232.233
• InChiKey: MKRRGGRYAFVXFU-RNFRBKRXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  O,O'-sec-butylidene-L_g-tartaric acid dimethyl ester 在 potassium cyanide 、 sodium hydroxide 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 26.5h， 生成 (4R)-2-[(4R,5R)-2-ethyl-2-methyl-5-[(4R)-4-naphthalen-2-yl-4,5-dihydro-1,3-oxazol-2-yl]-1,3-dioxolan-4-yl]-4-naphthalen-2-yl-4,5-dihydro-1,3-oxazole
  参考文献：
  名称：

  Enantioselective Mercuriocyclization of γ-Hydroxy-cis-alkenes

  摘要：

  Asymmetric mercuriocyclization of gamma-hydroxy-(Z)-alkenes has been achieved using Hg(II) complexed with tartrate-derived 4-(2-naphthyl)bisoxazoline as chiral ligand to give rise to 2-monosubstituted tetrahydrofurans in 86-95% ee. Not only the linker connecting two oxazolines but also their 4-substituents were found crucial for high enantioselectivity. In addition, tuning the ketal protecting group of tartrate as well as adding MeOH and K(2)CO(3) worked beneficially.

  DOI：

  10.1021/ja029777d
• 作为产物：
  描述：

  L-(+)-酒石酸二甲酯 、 丁酮 在 phosphorus pentoxide 作用下， 生成 O,O'-sec-butylidene-L_g-tartaric acid dimethyl ester
  参考文献：
  名称：

  Synthesis of Cyclic Derivatives of Tartaric Acid by Condensing Alkyld-Tartrates with Aliphatic Ketones. (Optical Activity and Chemical Structure in Tartaric Acid. V)

  摘要：

  DOI：

  10.1246/bcsj.14.19

文献信息

• Synthesis of Cyclic Derivatives of Tartaric Acid by Condensing Alkyl<i>d</i>-Tartrates with Aliphatic Ketones. (Optical Activity and Chemical Structure in Tartaric Acid. V)
  作者：Yojiro Tsuzuki

  DOI：10.1246/bcsj.14.19

  日期：1939.1
• Enantioselective Mercuriocyclization of γ-Hydroxy-<i>cis</i>-alkenes
  作者：Sung Ho Kang、Mihyong Kim

  DOI：10.1021/ja029777d

  日期：2003.4.1

  Asymmetric mercuriocyclization of gamma-hydroxy-(Z)-alkenes has been achieved using Hg(II) complexed with tartrate-derived 4-(2-naphthyl)bisoxazoline as chiral ligand to give rise to 2-monosubstituted tetrahydrofurans in 86-95% ee. Not only the linker connecting two oxazolines but also their 4-substituents were found crucial for high enantioselectivity. In addition, tuning the ketal protecting group of tartrate as well as adding MeOH and K(2)CO(3) worked beneficially.