(4S,5S)-4,5-diphenyl-(1,3,2)-dioxathiolane-(2,2)-dioxide | 214492-40-7

• 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: (4S,5S)-4,5-diphenyl-(1,3,2)-dioxathiolane-(2,2)-dioxide
• 英文别名: (4S,5S)-4,5-diphenyl-1,3,2-dioxathiolane 2,2-dioxide
• CAS: 214492-40-7
• 化学式: C₁₄H₁₂O₄S
• 分子量: 276.313
• InChiKey: ZRHYPUWGNKZMRW-KBPBESRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  61
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4S,5S)-4,5-diphenyl-(1,3,2)-dioxathiolane-(2,2)-dioxide 在 碲化氢 、 三乙基硼氢化锂 作用下， 以 四氢呋喃 为溶剂， 反应 0.33h， 以95%的产率得到反式-1,2-二苯乙烯
  参考文献：
  名称：

  通过碲化学法从1,2-二醇的环状硫酸盐和硫代碳酸盐中制得的烯烃

  摘要：

  通过元素还原原位生成的碲化物离子处理1,2-二醇环状硫酸盐（1,3,2-二氧杂硫杂环戊烷2,2-二氧化物），在温和的条件下（10分钟至2小时）快速产生烯烃。 0°C至室温）。该反应是立体特异性的，例如内消旋-2,3-二苯基乙烷2,3-二醇→顺式-sti; d，l -2,3-二苯基乙烷-2,3-二醇→反式-sti。已经获得了不饱和的甘露糖和核糖衍生物，（-）-酒石酸二乙酯得到了富马酸二乙酯。该反应可以在化学计量的还原剂存在下用0.1当量或更少的元素碲进行。碲化物离子与内消旋的环状硫代碳酸酯（1,3-二氧戊环-2-硫酮）反应-和d，1-，1,2-二苯基乙烷-1,2-二醇分别产生顺式-和反式-二苯乙烯。

  DOI：

  10.1016/0040-4039(95)01532-m
• 作为产物：
  描述：

  (4S,5S)-4,5-diphenyl-1,3,2-dioxathiolane 2-oxide 在 ruthenium trichloride 、 sodium periodate 作用下， 以 四氯化碳 、 乙腈 为溶剂， 反应 1.0h， 生成 (4S,5S)-4,5-diphenyl-(1,3,2)-dioxathiolane-(2,2)-dioxide
  参考文献：
  名称：

  Conformational Preferences of RNase A C-Peptide Derivatives Containing a Highly Constrained Analogue of Phenylalanine

  摘要：

  Both enantiomers of a highly constrained derivative of phenylalanine, FiFi, were prepared in optically pure form. Studies were performed to elucidate the effects of substituting this amino acid for phenylalanine in RN-24, a derivative of the RNase A C-peptide. Thus RN-24, and the analogues 9 and 10, in which Phe-8 was replaced by each of the enantiomers of FiFi, were prepared. Comparative circular dichroism (CD) experiments indicated relative tendencies to adopt helical structures, and variable-temperature CD studies showed the relative ease with which these conformations were lost at elevated temperatures. These observations were rationalized via computer-assisted molecular modeling, which showed that the phenyl groups of (R,R)-FiFi in the peptidomimetic 9 can be accommodated via distortion of the helical conformations and that such distorted conformations persist as the temperature is increased. Conversely, intolerable contacts occur in an analogous conformation of the (S,S)-FiFi peptidomimetic 10 and these preclude helicity. Consistent with these observations, molecular dynamics studies of these peptidomimetics at 276 K indicate that helical conformations of 9 and RN-24 are observable under conditions in which the analogous conformation of 10 is lost. Overall, these studies demonstrate that cyclopropane amino acids can be used to enforce elements of secondary structure (albeit distorted) or to preclude them altogether.

  DOI：

  10.1021/ja981153d

文献信息

• Alkenes from cyclic sulfates and thionocarbonates of 1,2-diols via tellurium chemistry
  作者：Bin Chao、Kenneth C. McNulty、Donald C. Dittmer

  DOI：10.1016/0040-4039(95)01532-m

  日期：1995.10

  stereospecific, e.g. meso-2,3-diphenylethane 2,3-diol → cis-stilbene; d,l-2,3-diphenylethane-2,3-diol → trans-stilbene. Unsaturated mannose and ribose derivatives have been obtained, and diethyl (-)-tartrate gives diethyl fumarate. The reaction may be performed with 0.1 equiv or less of elemental tellurium in the presence of a stoichiometric amount of reducing agent. Reaction of telluride ion with cyclic thionocarbonates

  通过元素还原原位生成的碲化物离子处理1,2-二醇环状硫酸盐（1,3,2-二氧杂硫杂环戊烷2,2-二氧化物），在温和的条件下（10分钟至2小时）快速产生烯烃。 0°C至室温）。该反应是立体特异性的，例如内消旋-2,3-二苯基乙烷2,3-二醇→顺式-sti; d，l -2,3-二苯基乙烷-2,3-二醇→反式-sti。已经获得了不饱和的甘露糖和核糖衍生物，（-）-酒石酸二乙酯得到了富马酸二乙酯。该反应可以在化学计量的还原剂存在下用0.1当量或更少的元素碲进行。碲化物离子与内消旋的环状硫代碳酸酯（1,3-二氧戊环-2-硫酮）反应-和d，1-，1,2-二苯基乙烷-1,2-二醇分别产生顺式-和反式-二苯乙烯。
• Conformational Preferences of RNase A <i>C</i>-Peptide Derivatives Containing a Highly Constrained Analogue of Phenylalanine
  作者：Destardi Moye-Sherman、Song Jin、Inhye Ham、Dongyeol Lim、J. Martin Scholtz、Kevin Burgess

  DOI：10.1021/ja981153d

  日期：1998.9.1

  Both enantiomers of a highly constrained derivative of phenylalanine, FiFi, were prepared in optically pure form. Studies were performed to elucidate the effects of substituting this amino acid for phenylalanine in RN-24, a derivative of the RNase A C-peptide. Thus RN-24, and the analogues 9 and 10, in which Phe-8 was replaced by each of the enantiomers of FiFi, were prepared. Comparative circular dichroism (CD) experiments indicated relative tendencies to adopt helical structures, and variable-temperature CD studies showed the relative ease with which these conformations were lost at elevated temperatures. These observations were rationalized via computer-assisted molecular modeling, which showed that the phenyl groups of (R,R)-FiFi in the peptidomimetic 9 can be accommodated via distortion of the helical conformations and that such distorted conformations persist as the temperature is increased. Conversely, intolerable contacts occur in an analogous conformation of the (S,S)-FiFi peptidomimetic 10 and these preclude helicity. Consistent with these observations, molecular dynamics studies of these peptidomimetics at 276 K indicate that helical conformations of 9 and RN-24 are observable under conditions in which the analogous conformation of 10 is lost. Overall, these studies demonstrate that cyclopropane amino acids can be used to enforce elements of secondary structure (albeit distorted) or to preclude them altogether.