S-1,1-二苯基-1,2-丙二醇 | 126577-48-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: S-1,1-二苯基-1,2-丙二醇
• 英文名称: (R)-(+)-1,1-diphenyl-1,2-propanediol
• 英文别名: (R)-1,1-Diphenyl-1,2-propandiol；(2R)-1,1-diphenylpropane-1,2-diol
• CAS: 126577-48-8
• 化学式: C₁₅H₁₆O₂
• 分子量: 228.291
• InChiKey: RQKXFLUAQLDHMO-GFCCVEGCSA-N

物化性质

• 沸点：
  406.6±40.0 °C(Predicted)
• 密度：
  1.152±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  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 二氯甲烷 为溶剂， 以60%的产率得到2-Methyl-1,1-diphenylethylensulfit
  参考文献：
  名称：

  A general route to enantiomerically pure sulfoxides from a chiral sulfite

  摘要：

  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.

  DOI：

  10.1021/jo00021a008
• 作为产物：
  描述：

  (R)-1,1-diphenyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propan-1-ol 在 sodium perborate tetrahydrate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 2.0h， 以2.7 mg的产率得到S-1,1-二苯基-1,2-丙二醇
  参考文献：
  名称：

  对映体和非对映体选择性1,2-具有二硼烷基甲烷和取代的1,1-二硼烷基烷烃的α-酮酸酯

  摘要：

  据报道，通过在α-酮酸酯中添加二硼烷基甲烷和取代的1,1-二硼烷基烷烃，可以催化合成硼酸酯取代的叔醇。反应由容易获得的手性膦/铜（I）配合物催化，并产生β-羟基硼酸酯，其含高达99：1 er和大于20：1 dr的多达两个连续的立体异构中心。有机硼产品的实用性通过几种化学选择性功能化。有证据表明反应是通过对映体富集的α-硼烷基-铜烷基中间体发生的。

  DOI：

  10.1002/anie.201603465

文献信息

• Metal-Free Nitrogen-Doped Porous Carbons for Nitriles and Amides Synthesis from 1,2-Diols via Oxidative Cleavage of C–C Bonds
  作者：Huihui Luo、Ying Lv、Shuainan Tian、Guosong Li、Wen Dai

  DOI：10.1021/acscatal.3c03584

  日期：2023.11.17

  experiments verify that the preference of selectivity for amides stems from the synergistic effect of the carboxylic acid group in catalysts and carboxylate anions. This protocol exhibits easy scalability, broad substrate scope, remarkable functional group tolerability, and recyclable catalyst. Characterization analysis and experimental data reveal that the high catalytic activity of the N-doped carbon materials

  1,2-二醇中 C-C 键的氧化裂解和功能化已成为化学转化领域快速发展的领域。然而，由于 C-C 键固有的动力学惰性和热力学稳定性，以直接和选择性的方式实现这一目标，特别是使用无金属催化剂，仍然具有挑战性。在此，我们描述了一种通用且有效的无金属 N 掺杂多孔碳材料，该材料能够从 1,2-二醇合成腈。使用 O 2作为氧化剂和水溶液，一系列结构不同的单取代和多取代 1,2-二醇可以顺利地进行 C-C 键断裂以获得腈。NH 3作为氮源。值得注意的是，1,2-二醇的氧化裂解和酰胺化以产生酰胺也可以用NH 4 OAc作为氮源来实现。一系列对照实验验证了酰胺选择性的偏好源于催化剂中的羧酸基团和羧酸根阴离子的协同效应。该协议具有简单的可扩展性、广泛的底物范围、显着的官能团耐受性和可回收的催化剂。表征分析和实验数据表明，氮掺杂碳材料的高催化活性主要归因于石墨氮物种和大的比表面积。
• REBIERE, F.;KAGAN, H. B., TETRAHEDRON LETT., 30,(1989) N8, C. 3659-3662
  作者：REBIERE, F.、KAGAN, H. B.

  DOI：——

  日期：——
• Enantio- and Diastereoselective 1,2-Additions to α-Ketoesters with Diborylmethane and Substituted 1,1-Diborylalkanes
  作者：Stephanie A. Murray、Jacob C. Green、Sanita B. Tailor、Simon J. Meek

  DOI：10.1002/anie.201603465

  日期：2016.7.25

  The catalytic enantioselective synthesis of boronate‐substituted tertiary alcohols through additions of diborylmethane and substituted 1,1‐diborylalkanes to α‐ketoesters is reported. The reactions are catalyzed by readily available chiral phosphine/copper(I) complexes and produce β‐hydroxyboronates containing up to two contiguous stereogenic centers in up to 99:1 e.r. and greater than 20:1 d.r. The utility

  据报道，通过在α-酮酸酯中添加二硼烷基甲烷和取代的1,1-二硼烷基烷烃，可以催化合成硼酸酯取代的叔醇。反应由容易获得的手性膦/铜（I）配合物催化，并产生β-羟基硼酸酯，其含高达99：1 er和大于20：1 dr的多达两个连续的立体异构中心。有机硼产品的实用性通过几种化学选择性功能化。有证据表明反应是通过对映体富集的α-硼烷基-铜烷基中间体发生的。
• 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.