(R,R)-(+)-4,5-diphenyl-1,3,2-dioxathiolan-2-one | 183184-04-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (R,R)-(+)-4,5-diphenyl-1,3,2-dioxathiolan-2-one
• 英文别名: cycl. 1α,2β-Diphenyl-ethylensulfit；(4R,5R)-4,5-diphenyl-1,3,2-dioxathiolane 2-oxide
• CAS: 183184-04-5
• 化学式: C₁₄H₁₂O₃S
• 分子量: 260.313
• InChiKey: QFXSAPIDISAYKZ-ZIAGYGMSSA-N

物化性质

• 沸点：
  393.7±42.0 °C(Predicted)
• 密度：
  1.38±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 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：

  (R,R)-(+)-4,5-diphenyl-1,3,2-dioxathiolan-2-one 在 lithium aluminium tetrahydride 、 叠氮化锂 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 (1R,2S)-2-氨基-1,2-二苯基乙醇
  参考文献：
  名称：

  通过手性环状亚硫酸盐合成手性氨基醇，氮丙啶和二胺

  摘要：

  邻苯二甲酸二醇与亚硫酰氯反应，以定量收率得到1,2-环亚硫酸盐，二甲基甲酰胺中的叠氮化锂可轻松使开环生成叠氮基醇，而叠氮基醇又被立体选择性地转化为氨基醇，氮丙啶和二胺。

  DOI：

  10.1039/c39910000095
• 作为产物：
  描述：

  氢胺 在 氯化亚砜 作用下， 以74%的产率得到(R,R)-(+)-4,5-diphenyl-1,3,2-dioxathiolan-2-one
  参考文献：
  名称：

  对映体富集的氮丙啶的溶剂和温度依赖性官能化

  摘要：

  据报道，手性非外消旋氮丙啶具有高度立体选择性和区域选择性功能。通过从母体对映体富集的氮丙啶开始并精细调节反应条件，可以解决锂化/亲电子捕获序列的区域选择性和立体选择性，从而可以制备高度对映体的官能化氮丙啶。从手性Ñ烷基反式-2,3- diphenylaziridines（小号，小号） - 1，b中，两个不同构造的手性aziridinyllithiums可以产生（反式- 1，B-锂在甲苯中，顺式- 1一，b-Li在THF中），因此揭示了溶剂依赖的反应性，可用于合成具有不同立体化学的手性三取代氮丙啶。相比之下，手性氮丙啶（S，S）-1 c表现出温度依赖性，可在-78°C时得到手性邻甲硅烷基化的氮丙啶1 c-邻-Li，在0 ℃时得到α-锂化的氮丙啶1c-α-Li ℃。两种锂化中间体均与亲电试剂反应生成对映体富集的邻位-和α-官能化的氮丙啶。的反应的所有锂化氮丙啶与羰基化合物布置有用的手性羟烷基化

  DOI：

  10.1002/chem.201002172

文献信息

• Preparation of Cyclic Sulfites by Transesterification of Diols and Diisopropyl Sulfite
  作者：Steven A. King、Brenda Pipik、David A. Conlon、M. Bhupathy

  DOI：10.1080/00397919708003344

  日期：1997.2

  Abstract Cyclic Sulfites of 1,2-, 1,3- and 1,4-diols can be prepared in high yield by acid or base catalyzed transesterification with diisopropyl sulfite.

  摘要 1,2-、1,3-和1,4-二醇的环状亚硫酸盐可以通过酸或碱催化与亚硫酸二异丙酯的酯交换反应以高收率制备。
• The Pyrolysis of Sulfites. I. Symmetrical Sulfites
  作者：Charles C. Price、Giancarlo Berti

  DOI：10.1021/ja01634a001

  日期：1954.3
• Nucleophilic Ring Opening of Cyclic 1,2-Sulfites with Nitrogen Nucleophiles. A Route to Enantiopure Benzylic Amino Alcohols.
  作者：Kirsten Nymann、Saravanapavan Mylvaganam、John S. Svendsen、Inamur Rahaman Laskar、Nirmalendu Ray Chaudhuri、Kirsi Ranta、Teófilo Rojo

  DOI：10.3891/acta.chem.scand.52-1060

  日期：——

  The reaction between cyclic 1,2-sulfites and two imide and two sulfonamide nucleophiles has been Investigated in order to develop a procedure for the enantioselective preparation of N-protected vicinal amino alcohols. The results show that both imide and sulfonamide anions react with cyclic sulfites, yielding the desired products. In some cases the regioselectivities are low, and for the sulfonamides products originating from nucleophilic addition to the sulfite sulfur are observed.
• Nucleophilic Reactions between Cyclic 1,2-Sulfites and Chloride Ions.
  作者：Kirsten Nymann、Linda Jensen、John S. Svendsen、T. Anthonsen、Ryszard Gawinecki、Günter Häfelinger、Muhammed Nour Homsi、Frank K. H. Kuske、Monika Haugg、Nathalie Trabesinger-Rüf、Elmar G. Weinhold

  DOI：10.3891/acta.chem.scand.50-0832

  日期：——

  When cyclic 1,2-sulfites are ring opened by chloride ion, the chlorohydrins are formed with low regio and stereo-selectivity. The mechanisms involved in the process were investigated by measuring the stereochemical outcome of the reactions. The results showed that reversible inversion pathways (S(N)2 reactions) and a retention pathway (S(N)2i reaction) gave rise to the loss in ee in both the chlorohydrins and in the cyclic 1,2-sulfites.
• Induction of Cholesteric Mesophases by Simple Cyclic Derivatives of <i>p,p</i><i>‘</i>-Disubstituted 1,2-Diphenylethane-1,2-diols:  Importance of Shape and Polarizability Effects
  作者：Stefano Superchi、Maria Irene Donnoli、Gloria Proni、Gian Piero Spada、Carlo Rosini

  DOI：10.1021/jo990038y

  日期：1999.6.1

  A systematic study of the cholesteric induction in nematic solvents (MBBA and E7) by some cyclic derivatives of unsubstituted and p,p'-disubstituted-1,2-diphenylethane-1, shows that the values of the twisting power are significantly dependent on the nature of the link connecting the two oxygen atoms and on the nature of the p,p'-substituents. This result has been interpreted considering that the nature of the bridge affects the overall molecular shape and the p,p'-substituents affect both the molecular polarizability and shape. This investigation points out that the polarizability of the solute and the solvent is the main parameter in determining the value of the twisting power while electrostatic arene-arene interactions contribute to a less extent. It has been also observed that solutes having the same structure and the same absolute configuration can induce cholesteric helix of opposite sign depending on the substituent on the aromatic ring. This finding indicates that configurational assignments by cholesteric induction are reliable only if high values of twisting power are measured.