α,α'-di<(S)-2-hydroxy-2-phenylethyl>-o-xylenedioxide | 141515-87-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: α,α'-di<(S)-2-hydroxy-2-phenylethyl>-o-xylenedioxide
• 英文别名: α,α'-di[(S)-2-hydroxy-2-phenylethyl]-o-xylenedioxide；(1S)-2-[[2-[[(2S)-2-hydroxy-2-phenylethoxy]methyl]phenyl]methoxy]-1-phenylethanol
• CAS: 141515-87-9
• 化学式: C₂₄H₂₆O₄
• 分子量: 378.468
• InChiKey: IILWVQRUEDPTLM-DNQXCXABSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  28
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  L-扁桃酸甲酯 在 lithium aluminium tetrahydride 、 sodium hydride 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 2.17h， 生成 α,α'-di<(S)-2-hydroxy-2-phenylethyl>-o-xylenedioxide
  参考文献：
  名称：

  Enantioselective protonation of samarium enolates by a C2-symmetric chiral diol

  摘要：

  High enantioselectivity (up to 97%ee) have been achieved in the protonation of samarium enolates which were generated by SmI2-mediated cross-coupling reaction between unsymmtrical dialkylketene and allyl iodide, using a C-2-symmetric chiral diol as a proton source. The stereochemistry of enolate formation and of the enantioselective protonation is discussed.

  DOI：

  10.1016/0957-4166(94)80086-3

文献信息

• Enantioselective protonation of samarium enolates derived from α-heterosubstituted ketones and lactone by SmI2-mediated reduction
  作者：Yutaka Nakamura、Seiji Takeuchi、Yoshiaki Ohgo、Makoto Yamaoka、Akihiro Yoshida、Koichi Mikami

  DOI：10.1016/s0040-4020(99)00143-x

  日期：1999.4

  SmI2-mediated reductive cleavage of α-hetero substituents of α-alkyl or α-aryl ketones and lactone gave the corresponding “thermodynamic samarium enolates”. Enantioselective protonation of the samarium enolates with C2-symmetric chiral diols afforded the corresponding ketones and lactone in moderate to high enantioselectivities.

  SmI 2介导的α-烷基或α-芳基酮的α-杂取代基和内酯的还原裂解产生相应的“热力学sa烯醇盐”。用C 2对称手性二醇对烯醇盐进行对映选择性质子化，可得到中等至高对映选择性的相应酮和内酯。
• Asymmetric Synthesis of Ketones by SmI₂-Mediated Allylation or Benzylation of Ketenes Followed by Enantioselective Protonation
  作者：Seiji Takeuchi、Norikazu Miyoshi、Yoshiaki Ohgo

  DOI：10.1246/cl.1992.551

  日期：1992.4

  SmI2-mediated allylation or benzylation of alkylarylketenes followed by enantioselective protonation with α,α′-di[(S)-2-hydroxy-2-phenylethyl]-o-xylenedioxide gave the corresponding ketones in 61–91%ee.

  SmI2- 介导的烷基芳基烯酮的烯丙基化或苄基化，然后与 α,α′-二[(S)-2-羟基-2-苯基乙基]-邻氧二氧化物进行对映选择性质子化，可得到 61-91%ee 的相应酮。
• Enantioselective protonation of samarium enolates by a C2-symmetric chiral diol
  作者：Seiji Takeuchi、Akiko Ohira、Norikazu Miyoshi、Hajime Mashio、Yoshiaki Ohgo

  DOI：10.1016/0957-4166(94)80086-3

  日期：1994.9

  High enantioselectivity (up to 97%ee) have been achieved in the protonation of samarium enolates which were generated by SmI2-mediated cross-coupling reaction between unsymmtrical dialkylketene and allyl iodide, using a C-2-symmetric chiral diol as a proton source. The stereochemistry of enolate formation and of the enantioselective protonation is discussed.