(2S,5S)-5-methyl-4,4-diphenyl-1,3,2-dioxathiolane-2-oxide | 126577-50-2

• 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: (2S,5S)-5-methyl-4,4-diphenyl-1,3,2-dioxathiolane-2-oxide
• 英文别名: 2-Methyl-1,1-diphenylethylensulfit；(2S,5S)-5-methyl-4,4-diphenyl-1,3,2-dioxathiolane 2-oxide
• CAS: 126577-50-2
• 化学式: C₁₅H₁₄O₃S
• 分子量: 274.34
• InChiKey: ACONWRLGPDTDKX-BUXKBTBVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  54.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,5S)-5-methyl-4,4-diphenyl-1,3,2-dioxathiolane-2-oxide 、 叔丁基氯化镁 生成 (2S,S(S))-3-hydroxy-3,3-diphenylpropyl 1,1-dimethylethanesulfinate
  参考文献：
  名称：

  RICARD, LOUIS;REBIERE, FRANCOIS;KAGAN, HENRI B., C. R. ACAD. SCI. SER. 2, 312,(1991) N, C. 225-228

  摘要：

  DOI：
• 作为产物：
  描述：

  (S)-(-)-1,1-二苯基-1,2-丙二醇 在 氯化亚砜 、 三乙胺 作用下， 以70%的产率得到(2R,5S)-trans-4,4-diphenyl-5-methyl-1,3,2-dioxathiolane 2-oxide
  参考文献：
  名称：

  Kagan, Henry B.; Rebiere, Francois; Samuel, Odile, Phosphorus, Sulfur and Silicon and the Related Elements, 1991, vol. 58, # 1-4, p. 89 - 110

  摘要：

  DOI：

文献信息

• A general route to enantiomerically pure sulfoxides from a chiral sulfite
  作者：F. Rebiere、O. Samuel、L. Ricard、H. B. Kagan

  DOI：10.1021/jo00021a008

  日期：1991.10

  Enantiomerically pure cyclic chiral sulfite (S)-7 (trans stereochemistry) has been easily obtained in two steps from (S)-ethyl lactate. This compound was found to react cleanly with many organometallics to give crystalline sulfinates with high regioselectivity (> 90:10). Addition of a second organometallic transforms the purified sulfinate in excellent yield into a chiral sulfoxide (100% ee) of predictable absolute configuration. The mechanism and scope of this approach are discussed. This method completes the various other methods of preparation of chiral sulfoxides and is especially convenient for the preparation of tert-butyl sulfoxides. Examples for the synthesis of many chiral tert-butyl sulfoxides are given. The case of chiral sulfites derived from a C2 diol or of a chiral monoalcohol is also proposed as a route to chiral sulfinates, and some promising preliminary results have been obtained. The general main routes to obtain chiral sulfoxides from sulfites are also discussed.
• RICARD, LOUIS;REBIERE, FRANCOIS;KAGAN, HENRI B., C. R. ACAD. SCI. SER. 2, 312,(1991) N, C. 225-228
  作者：RICARD, LOUIS、REBIERE, FRANCOIS、KAGAN, HENRI B.

  DOI：——

  日期：——
• Kagan, Henry B.; Rebiere, Francois; Samuel, Odile, Phosphorus, Sulfur and Silicon and the Related Elements, 1991, vol. 58, # 1-4, p. 89 - 110
  作者：Kagan, Henry B.、Rebiere, Francois、Samuel, Odile

  DOI：——

  日期：——